8 comments/ 64094 views/ 6 favorites Amy's First Time By: LaxNd20 Please give me feedback (good or bad). I'd like to know what others think, thank you. Send them to the address in my profile with the headline "Amy's First" * * * * * It was Saturday night; Amy had just gotten off work and was headed back to the apartment she shared with her two friends Jill and Kelly. Amy had only really known the two girls for about 2 months; she had just moved to the city and had met them in a bar. They had an open room in the apartment and offered it to her. Amy was 23, 5'7", 110lbs., 36B, blonde hair. She walked into the apartment and found Jill sitting at the table reading. Jill was about 24, 6'1", 120lbs, 34C, and brunette. All the guys wanted to fuck her, especially since she was a former track standout in college. Kelly was in the bathroom getting out of the shower. She was 24 also, 5'11", 113lbs, 36C, and dirty blonde. She walked out of the shower past the other two in only a towel. She walked into her bedroom and closed the door. Jill and Amy were talking about their days when they herd Kelly calling from the room, "Guys, could you come in here?" The two of them went to see what was up. Kelly sat in the middle of the room with a deck of cards in her hand. "Let's play some poker!" Jill's eyes lit up and said, "Okay, how much is the buy in, $5?" Kelly got a devilish grin on her face, "No. How about we play some strip poker?" Jill sat down and said, "Sure." Amy stood there for a second and then asked, "Why are we going to play strip poker alone?" The two girls just kind of giggled at her and then Kelly said, "Well, Amy, me and Jill are bi-sexual and play ever once in a while when we get horny, you don't have to play is you don't want to." Amy was a little stunned; she had never thought these two girls were bi. She had always seen them with guys and had once walked in on Jill giving a guy head. Amy had never had a bi experience and was kind of curious. "Well, ok, I'd like to play, but what are the rules?" Jill spoke up first and said, "Ok, the rules are this: each of us wears four items of clothing on: a shirt; bra; pants; panties. There is no folding; the player with the worst hand has to take off a piece of clothing, as directed by the winner. After a player has lost all there clothing they can continue to play, but if they come in last again, they have to stay naked the whole night and do anything the winner of that hand asks for the rest of the night. Is that ok with you?" Amy was never really good as poker but she was starting to get a little wet and the idea interested her. She sat down and got ready to play. Kelly dealt first while Jill got a bottle of wine and three glasses. Kelly won the first hand and Jill lost it. Kelly told Jill to take off her top. The next hand Amy won and Jill lost. Amy told Jill to take off her pants. Jill stood up and slowly wiggled out of her jeans. She was now left in a matching set of black lace bra and panties. Jill won the next hand and Amy lost. Amy had to take off her shirt, exposing her light blue bra. Kelly lost the next hand and had to take off her top, leaving her to show her red bra. Amy lost the next hand and took off her pants, revealing a small wet spot in her light blue cotton thong. "Ooo, looks like someone is enjoying herself" Jill said. Amy sat down a little embarrassed and played the next hand which she won over Jill. Jill then stood up, walked to Amy, knelt down and unstrapped her bra letting her tits fall almost into Amy's face. She then handed her bra to Amy and moved away giggling. Kelly then beat Amy making her take off her bra. Her tits were tan (she bathed topless) with small nipples like Jill. Jill then beat Kelly making her take off her pants to show her red mini thong. Kelly lost the next hand to Amy leaving all three girls topless. Kelly beat Jill on the next hand. "Mmm," Kelly said. "Get your sexy ass over here and let me take off those panties." Jill went over and Kelly put her face right up to her crotch and pulled down her panties to show her completely shaved pussy. Her lips were moist and Kelly wanted to lick them, but not yet. Amy lost the next hand and Jill let her just slip off her thong, trying to stay a little modest. Amy too was completely shaved, but her lips were much wetter. "Amy, you can quit now if you would like, but if you continue, and lose, you have to do whatever the winner asks, ok?" Jill informed her. "I want to continue." "Wonderful, we are going to have an amazing evening then." Kelly said with a smile. Kelly lost the next hand to Amy who asked to have the thong when she took it off. Kelly threw it to her and Amy sniffed it and put it down. "Smells wonderful. I can't wait to win." Jill lost the next hand to Kelly. "Well, what do we have here? Looks like you are mine for the night." Kelly said. "I can't wait to see what kinky things you will have me do tonight." "That will come soon enough; first, this is the last hand, so until it is through, please play with yourself for us as we play." Jill began to rub her tits with her left hand as she started massaging her pussy lips. Amy watched her as she did this and became increasingly wet. Finally the last cards were dealt. Amy had two pair, 6's and Kings and a two. She handed in her two and got a three back. Not much help, but she still had a good hand. She laid it down and said, "Beat that!" Kelly looked a little up set and laid down her two cards, a measly pair of 4's. "Wow, I won," Amy said. "Not quite, I also have another 4!" Kelly said as she revealed her other four. "I win!" Amy was shocked, but figured it was better this way, she had no clue what to do with Kelly for the night. "Ok, nice hand. So this means that I'm your toy tonight?" "Yes, it does," Kelly said as she stood up. "Now if you would be so kind as to move to my bed and lie down." Amy stood up and did so. She laid down on the bed a little unsure. "Now Jill, what I want you to do is show Amy a good time while I go get something." Jill, who was starting to breath heavily, took her two fingers out of her pussy, dripping with her juices. She walked up to Kelly and let she suck the juices off her fingers. Kelly then left and Jill slapped her on the ass as she was going. "Amy, are you nervous?" "A little." "Have you ever been with a woman before?" "No, but I guess I've always wanted to." "Well, I will be gentle, and if you like or don't like something, speak up and I will respond how you want." "Ok." Jill proceeded to climb into bed and lie down next to Amy. She gently kissed her cheek. She looked deep into her eyes and wet her lips. She then went and kissed Amy on the lips. She gently parted Amy's lips and let her tongue explore. Her hands moved down Amy's body touching her breast and cupping her firm ass. Jill then broke the kiss and moved her way down Amy's body. She licked circles around Amy's nipples before moving her mouth over one. She began to softly suck on the nipple, gently biting it. As she did this she let her hand wander to Amy's shaved pussy, finding her hard clit. Amy had her hands all over Jill's lower back and ass, needing her fingers into the flesh. Jill began to lick a line down Amy's g\body, about to dive into her pussy when Kelly walked into the room. "Ok, Jill, that's enough for now. Will you two come with me?" Kelly asked. Jill reluctantly stopped herself from tasting Amy's sweet juices. They both got up out of the bed and kissed as they followed Kelly, letting their hands wander on each others bodies. Kelly led them to the bathroom, where she had some things set up. There were towels on the floor and glasses of water. Kelly looked at Jill who knew exactly what was going on. Kelly said to Jill and Amy, "Drink up girls, and quickly." They did so, but Amy was still confused. Kelly then said to Jill, "I've already had two glasses of wine and two glasses of water, my bladder is about to burst. I want you to get on your knees and lick my pussy while I pee." Jill immediately got down on her knees and began to lap at Kelly's pussy. After about ten seconds, Kelly let out a loud moan as her flood gates opened and she began to pee. The hot yellow liquid had a sweet taste because of the wine and water. Jill let it fill her mouth and overflow before swallowing it. The stream, which seemed to last forever, filled Jill's mouth four times, and soaked Jill's tits, hair and entire face. When she had finished peeing, Kelly stopped Jill and said to Amy, "I want to you kiss her and lick my pee off her face and tits." Amy didn't know what to do, she had once seen a weird porno with her boyfriend that had a little watersports in it, but she had never considered it. Finally she decided that she would try it once and then decide from there. She licked Jill's chin first, tasting the sweet, salty, hot piss. She liked it, a little. She then kissed Jill, letting the excess pee flow into her mouth through the kiss. Amy then broke it off and started sucking and licking Jill's tits. Kelly was pinching her nipples as Amy did this. Finally, Kelly told Amy to stop. "Now, Jill, do you have to pee?" Kelly asked. "Yes, I do. Badly." "Good. Amy, you are going to sit on my face. As I eat you out, you are going to drink her piss." Amy was very excited, she had liked Kelly's pee, she couldn't wait to taste it from the source. Also she was going to experience her first girl on girl orgasm, both giving and receiving. Kelly laid down on the towels as Amy positioned her above her so that he pussy lips were right over her mouth while her ass was over Kelly's chest. Jill then stood so that her cunt was right in front of Amy's mouth. Amy began to like Jill's lips, feeling and tasting the wetness. She had tasted her own juices before, but Jill's were much sweeter. Jill started her stream. It came fast and Amy wasn't ready. It splashed on her chin and tits, running down to the nose and mouth of Kelly. Amy kneeled there having her pussy licked by Kelly while trying to catch Jill's hot stream of piss in her mouth. She managed to get a couple of mouthfuls before Jill was through. She greedily swallowed them, enjoying every drop. As Jill cam down to kiss and lick her piss off of Amy, Amy was getting ready to cum in Kelly' mouth. Amy broke off the kiss and screamed, "I'm cumming!!!!" Exhausted, Amy slid from Kelly's mouth and collapsed onto the floor, breathing heavily. Kelly gave her no rest. Her face glistening with Amy's cum, Kelly again dove between Amy's legs to lap at her sweet cunt. Amy was catching her second wind when she felt her bladder start to build with pressure. "I have to pee!!" Amy said franticly. Kelly stopped licking her and said, "It's about time. I wand you to kneel above my mouth again, I want to taste every drop." Amy followed her instructions and knelt over her mouth. She had to gently press on her bladder in order to get the flow going, but once she did, it seemed like it would never stop. The yellow liquid came out so fast that Kelly started to gag. Amy stopped the stream for her so that she could adjust. Kelly laid there, drinking mouthful after mouthful of her sweet piss. The excess had gotten into Kelly's hair and all over the towels. As Amy was peeing, Jill laid down and started sucking on Kelly's tits, softly biting the nipples. When Amy was done she stood up and helped Kelly to her feet. "Alright girls," Kelly said, "time to shower off." The three girls got into the shower and turned the water on. All three were tired from the pee session and so the shower was a cool off time with only some heavy petting. when they got out of the shower they didn't bother to dry off. They went straight to Kelly's bed. "I want to taste another girl's cum." Amy said eagerly. "Ok, here's how it will work: Amy you will eat me out, I will dine on Jill's sweet cunt, and Jill will eat you." The three laid down in a circle of sorts and got situated. Amy dove right into Kelly's hot snatch. She knew what she liked and decided to try that. She sucked on her clit, until it was good and hard. then she started lapping at her lips and digging her tongue into her folds deeper. Because they were only using their tongues, it took awhile for the three of them to climax, but they all did at about the same time. They all collapsed and stayed in their positions as they drifted off to sleep. Amy's First Time “How did it happen with you?” Amy looked at the young man in her lap and slowly closed her eyes, her fingers drifting through his hair. “I was eighteen,” she leaned her head back on the wall and sat in silence, letting her mind drift aimlessly in thought. **************************************** Was I eighteen? I don’t remember really. I remember it was the night before my birthday and they had a party for me. Beth, she kept handing me glasses of champagne and telling me, “Mom said it was okay,” and “Don’t worry, it’s your birthday.” The champagne really hit me and I remember her pushing me towards the stairs, telling me to go to bed. “It’s after midnight,” she held me up by my elbow, “everyone is going to go home.” Why was she screaming? I made it up the stairs. I remember that much. Somehow I had gotten undressed and into my bed, I don’t remember how exactly. Then mommy came in and turned out the light and wished me happy birthday. She told me she’d have a special surprise for me when I woke up. I fell asleep. It was two-thirty and Beth came into my room. I remember that, because I looked at the clock and started to complain. She was lying in the bed next to me before I even woke up, under my covers. “Are you okay?” she asked me, her hand gently soothing my face, “I feel somehow responsible.” I remember telling her it was okay, and that I was feeling better. Her hand was so soft against my cheek, I still think back to how it felt. She stayed with me for a few more minutes like that, slowly pulling my head to her chest, until it was on top of her arm. I remember cuddling against her, against her breast. My head gently lodged over her arm. She kept running her fingers through my hair. I felt her other hand start to soothe my hip before sliding up and down my side. She pulled me in closer, her hand rising higher and higher until I felt her slowly circling my breast. I really didn’t realize what was happening, still in a daze from being woken up and not quite sober from the champagne earlier. I just stayed there and relaxed, her touch was so soothing, everything felt so good. “Is this okay,” she whispered softly towards my ear. I remember nodding yes almost immediately. Not really taking time to think about what was happening. She slid down into the bed a little more until we were face to face. She looked into my face for a little while, her hand still soothing my bare hips and side. “You are so sweet,” she whispered before gently placing her lips against mine. I kissed back almost instinctively. Her mouth was so wet and soft. I felt her tugging at her night shirt as our tongues slid together in each other’s mouth. I felt my body twitch with excitement when she pulled the shirt over her head and her soft breasts pressed against my bare chest. I reached my arm around her and caressed the small of her back, pulling her closer to me. Something started to come over me. I felt a sexual energy start to build inside of me, even though I was still half asleep. She slid her hand around to my back, slowly tracing her finger down to my bottom. I felt her legs spread open, using her hand to push my thigh between them. I felt her moistness pressing against my leg as her kisses became more and more passionate. Her hips writhed against my thigh. I hesitantly reached my hand down to touch her breast. They were so soft, so round. I let out an uncontrollable moan as I felt my hand drifting over her nipple. I opened my eyes. It’s the first time I really remember opening them. She was so beautiful. Her blue eyes radiant even in the dim light, her blonde hair easily evident. I looked into her eyes as I let my fingers tease and twist her nipple. She looked up at me smiling, her teeth barely biting her lower lip. I felt her hand drift further and further down into my bottom. She slowly caressed me back and forth until her fingers brushed deep between my legs. She lowered her body slowly, her fingers now reaching deeper and deeper inside of me. I arched my back, pressing my moist lips out to her hand. It felt so good. I had never felt anything like it, her little fingers caressing deep within me. I gasped as I felt her mouth start to surround my nipple, her hand squeezing and guiding my breast towards her mouth. My body shivered with excitement as her tongue rolled repeatedly over my nipple, her mouth suckling me in. I reached my hands behind her head and pulled her tighter to my chest. Her mouth felt so good pressed against me. She slowly parted my legs with one of hers as she shifted and suckled in my other breast. I felt my body tense and then quiver out of my control as I felt her thigh spreading me apart, pressing tightly between my legs. “Oh god,” I remember moaning loudly. She quick held her finger up to my mouth. I had almost forgotten where I was, almost lost myself in the moment. I bit my lip. My body felt like it was going to explode. Every touch of her hand or her mouth sent shivers down my spine. I reached out and massaged her, feeling her hair, her breasts, anything I could find to touch. She felt so soft, so perfect. I drifted my hands across her shoulders, feeling the soft skin up her neck as she leaned away from my breast. “That feels so incredible,” I half moaned, my head drifting down her cheek towards her mouth. I ran my finger over her lips, she pulled it in softly, her tongue sliding against it, soaking it. She took both her hands and grabbed the finger from her mouth. Slowly she backed away from me and spread her legs, pulling my hand down. She guided my finger between her legs. It was so wet, so hot. Even my own had never felt like that before. I found her clit and gently touched it. I felt her thighs twitch as I let my hand explore deeper and deeper, my body lying next to hers. I slowly slid my finger deep inside of her, my thumb gently parting her lips. She let out a moan, her body tensing. I bent over ran my tongue across her breast before slowly pulling the nipple to my mouth. Her nipple felt so good in my mouth, so soothing. I started lowering my body further and further down her. First kissing her side, then her hips and finally working my way between her legs. I used my hands to part her soft flesh, my tongue hesitantly exploring her, taking in the tastes and the smells. I felt my own body rushed with excitement as I let my tongue twist inside of her. She let out a groan as her hips pressed up against my face. I felt her legs tighten around me, her hands clutching at my head. My tongue pressed deeper and deeper inside of her. She was all I could smell, see, feel and taste. Her body broke into orgasm as my tongue writhed deep within her, her hips rotating against my face, covering me with her smell. Slowly her body relaxed, her breathing slowly returning to normal. I let my tongue drift around her legs and her hips for a while, my hands reaching up and caressing her belly. “Oh god is right,” she whispered as she pulled my face towards her. She started by gently kissing my forehead, then my face. Slowly she worked her way towards my mouth. I felt my body tense as our mouths met. I was so excited to think of her kissing me after what I had just done. Her smell still filled my mind. She let her tongue search inside of my mouth, my body melting more and more the longer we kissed. I felt her hands searching around me, feeling my breasts, my hips. “I think it’s your turn,” she cooed into my ear. I remember biting my lip I was so afraid. She lowered herself down my body, first kissing my breasts. I could have come right there, but she sensed my excitement and slowly drifted on. Her hands were everywhere, touching me. My skin felt electric. I remember lying there so still, afraid to move, to do anything. Her breasts felt so good against my thighs as she parted them. I remember her nipples pressing between my legs, rubbing me. She lowered her mouth to my lips and I felt my body jolt with excitement before she even parted my lips. Her tongue gently rolled over my thighs before burrowing between them. I let out a yelp as her tongue headed for my clit, slowly suckling her lips around it. My body broke into orgasm almost immediately. She pulled me into her mouth slowly pressing me back out, her tongue always shifting across me. My hips shot up towards her face, pressing her nose tight against me. I felt my body shake repeatedly, over and over, my hands gripping at the sheets for dear life. Beth kept sliding deeper and deeper inside of me, her hands touching me everywhere. I shook for what seemed like hours, her face pressed tightly between my legs, reaching places I didn’t know I had. Finally, as I felt my body calm down, she pulled herself up next to me. I could smell myself all over her face, my juices glistening on her cheeks. I leaned towards her and kissed her on the forehead and then all over her face, taking my own taste into my mouth with hers. I felt the stirring of excitement again as I moved my lips next to hers and let my tongue explore the mouth that had just brought me so much pleasure. I pulled her body tightly against mine, our lips locked until we fell asleep in each other’s arms. **************************************** “That’s it,” Amy looked down. “You mean to tell me that Aunt Beth was your first sexual experience?” the young man looked up into her eyes. Amy nodded. “Yes she was.” Amy reached her hands down and caressed his bare chest, “Yes she was.” Amy's First Time "Everyone tells me how beautiful I am," Amy sobbed into her hands, "but no one shows me how beautiful I am." Now knowing how to answer, Tom shifted his weight from one foot to the next nervously, his body swaying. "Amy, you are very beautiful," Tom stammered, "very beautiful, but how do I show you." Amy looked up at him, the tears still dripping down her cheeks. "It's not you, it's me, I'm eighteen years old and no one so much as wants to kiss me," Amy answered, a sullen look on her face. "No one wants to hold my hand even. Look at me now, crying, my makeup is a mess, and my clothes are all wrinkled." "You're a mess," Tom laughed, "but a beautiful mess." Amy fell forward into Tom's chest and let his arms engulf her. "Oh Tommy," she moaned, muffled against his shirt, "you are so good to me." She felt Tommy's embrace tighten around her, his strong hands gently massaging her back. All of the stresses of the day seemed to be lifting off of her shoulders. She turned her head sideways and let it rest against his chest, enjoying the soothing pressure of his hands against her back. "You can do that forever Tommy," she looked up at him, "it feels so good." She looked up at his face, and slowly lifted to her tiptoes, and closing her eyes gently pressed her lips to his. Tom's body instantly stiffened against Amy, his once gentle hands gripping into her back tightly. "I'm sorry," Amy backed away, "I don't know what came over me." Tom loosened his grasp. "Amy, I mean, Amy," Tom stammered, "what was that all about?" "I don't know, like I said I don't know what came over me," Amy cuddled back into Tom's chest. "But you were holding me awfully tight, and I could tell you liked it too." Amy coyly bit her lip and nodded her chin downward. She could feel him bulge against her abdomen, his face red from blushing. "Amy, I mean, it's not what you think," Tom looked away, pushing her off of his chest. "Stop this." "You know it feels good. You know you like it," Amy reached her hands out to his chest, and began massaging it through his shirt. "You've always said that you thought I was pretty, that any man would be lucky to have me." Amy wrapped her arms around Tom's neck, her face looking up into his. She pressed her lips against his neck, as he turned his head to look away. "Amy, stop, please." Tom protested, vainly pressing her off of him. Amy felt her body quivering as she ran her tongue gently over the lines of his neck. His taste began to fill her. "Why are you doing this?" Tom moaned, obviously enjoying himself but still pushing himself away, "Amy please stop." Amy continued and she worked her hands underneath her shirt. Her gentle licks became kisses. She could feel his pants throbbing against her belly, reinforcing her commitment. "Oh Tom," she paused, "I need someone to love me, to really love me." Amy forced a sad look on her face and looked into his eyes. "I need someone to love me, and I know you love me." She could see that it was working, that he was crumbling. "You do love me don't you?" She looked up at him and gently rubbed his arm, "because I love you." Tom bit his lip and nodded yes hesitantly. Amy moved closer. Her body felt electric, she could feel all over her nerve endings from the top of her head to her toes. She reached her arms around his neck pulling her body up until their lips met. "Amy, what are we doing," Tommy moaned, as their lips engulfed one another. Their tongues gently explored each other's mouths. Amy tilted her head back and ran her fingers across the nape of Tom's neck. The held their kiss for what felt like an eternity, their arms exploring each other. "Amy, this isn't right, we can't do anymore," Tom finally pulled away and raising his hands behind his neck, gently pulled Amy's arms from around him. Amy looked into his eyes to see how determined he was to stop. She could see the doubt creeping through his face. The agony of Tom's desire fighting was fighting his instinct to say no. She could sense it. "Tommy, I think you're beautiful and smart and funny, why wouldn't I want to be with someone like that? Like you?" Amy slowly lowered herself to her knees in front of him and began to unbuckle his pants. Tom started to talk, but quickly bit his lip as Amy's hand gently grasped his cock. "Oh Tommy, I love you," she looked up into his eyes just as she parted her lips to take him inside of her mouth. She felt him expanding inside of her. How she had dreamt of this day, of feeling him inside of her, of tasting him, smelling him. She wanted him so badly for so long and now she was finally achieving her goal. Her body was electric. She could feel each hair as it stood on end. She focused on him, on his pleasure like she had never done for anyone before. His taste was so exquisite and silky against her tongue. She began moving her head back and forth, slowly after first. She looked up at him, his face looked to be in half agony, half ecstasy. She felt so powerful, so in control of him. She made his face look like that. She was making him lose control. She sped up, his mouth moving over him faster and faster. She could feel him spasm in her mouth, his juices occasionally coating her tongue. Finally she slowed down. "Is it okay if I take my shirt off?" She looked up at Tom for his approval. Slowly she unbuttoned each button of her blouse and gently dropped the shirt to her arms. She saw him stare as her nipples almost immediately firmed in the cool air. "You like them?" She looked up at him and slowly stood up, making sure that her breasts gently rubbed against his each side of his throbbing cock. "Do you want to touch them?" She looked at him coyly, then gently put her hands into his and pulled them up to her chest. She felt like fainting as his hands firmly surrounded so strongly that her body felt like collapsing into his arms, letting him scoop her up and do whatever he wanted. She moaned softly as his hands finally relaxed and explored farther and farther across her body, until finally, once again their lips met in a long embrace. "Oh Tommy," Amy looked into his eyes, "I love you." Tommy looked away without answering. Deep in her heart Amy knew that he wanted this as much as she wanted it, it would only take a little time. "I need to feel you inside of me, I need to feel next to you, close to you," Amy continued. "Please Tommy." She slowly removed her pants. Tommy continued to look away, but remained so close to her that she could feel the heat radiating from his body. "Give me your hand," Amy held her hand out for him and then, with her fingers interlocked with his, pulled it between her legs. She felt his fingers explore her, her legs opening wider and wider. "Oh Tommy," she bit her lip and moaned, "I need you." She lowered herself to the floor and, still holding Tom's hand, pulled him on top of her. "Please Tommy," she looked into his eyes and begged, "Please." She could feel him so close to her, the heat from his cock burning against her thigh. She reached her lips to his and kissed it softly. Finally she felt him moving higher and higher up her body, his hands exploring her breasts while the tip of his cock gently parted her folds of moist flesh. Amy arched her back and let out a moan as his cock entered her agonizingly slowly. She looked up into Tom's eyes. He was so beautiful, so perfect. "Oh Tommy, you feel so good," she moaned repeatedly as he thrust himself gently in and out of her. She felt her hips moving involuntarily to meet each of his thrust, her legs shaking uncontrollably. "You are my first," she whispered into his ear as she felt her body quivering against his. "Oh my god," Tom started tried to quickly pull himself from between Amy's legs, "I'm going to come." Amy quickly twisted her legs over his buttocks and pressed her mouth hard against his. "Come inside of me," she moaned, "then pressed her hips as hard as she could against him. She felt his body convulse on top of her, his grunting and violent thrusting throwing her into the throes of her own orgasm. She could feel his juices spilling side of her, making his thrusts slide in and out faster and faster, until he finally collapsed on top of her. They lay together on the floor, locked in each other's arms for what seemed like an eternity, the afterglow of their sex evident on both of their faces. Amy looked up and smiled at Tom. "I am so glad that my first time was with you," she cooed. "Who could I love more than my brother?" Tom looked away, his hands continuing to caress her. Amy's First Time Amy brought her suitcase into the dorm room. Nobody was there yet, so she picked a bed and a dresser and started to unpack. Her mom had helped her pack her clothes – plain white cotton underwear, white undershirts, dark plain t-shirts, a couple pair of jeans, a couple long skirts and a couple button down blouses. Her parents did not want her to attract any attention from boys while she was studying. It had been that way during high school and also for the year she worked in their church after high school. She had not made any particularly good friends and had not even talked to any boys. Letting her go off to college was particularly hard for her parents, but also hard for her. She was very nervous. The door opened and a girl with dark skin and short curly hair came in. "Hi, I am Jonay," she said. I guess we are roommates. Amy thought her parents would be upset to have a colored person in her room, though her skin was light for a colored person – almost the color of honey. Jonay was actually half black and half white. Jonay threw her bag on the bed across from Amy and asked if the other roommate had shown up yet. "No," Amy said, "I think I was the first one here". A few minutes later a girl with bright red long hair came in. "Hi there! I'm Theresa," she said as she threw her things on the remaining bed. The three of them were quite a contrast. Jonay with her dark skin, dark eyes and dark hair, Theresa with her red hair, pale skin and green eyes and finally Amy with her medium length blonde hair, blue eyes and tan skin. The girls put their stuff away and decided to go explore. The first few weeks were so busy with finding classes, exams and studying that they barely had time to talk to each other. One Saturday morning Amy slept late and when she awoke both Theresa and Jonay were gone. She jumped in the shower and scrubbed quickly. After drying off, she put on her underwear and jeans. She began wrapping an ace bandage around her breasts as her mother had taught her. Suddenly the door to the bathroom burst open. "Oh, I didn't know you were in here! What are you doing?" Theresa couldn't believe her eyes when she saw what Amy was doing. "I'm wrapping myself so I don't attract attention. Don't you?" Amy said. She thought all girls did. At least that was what her mom had said. "No way!" Theresa exclaimed. "I want to be able to have feeling in my breasts and nipples." "Feeling?" Amy asked. Just then Jonay came in to see what was going on. "You won't believe this." Theresa told her what Amy was doing.. "Come over here" Jonay said and they led her to her bed. "Lay back and put this over your eyes" as she handed her a night mask. Amy covered her eyes and laid back not sure what they were going to do. Jonay and Theresa unwrapped the ace bandage. The air against Amy's nipples made them harden quickly. Both Jonay and Theresa then ran their fingers lightly around her small breasts and then stroked her nipples. "Wow" thought Amy that feels incredible. She had never even touched her own breasts or nipples. Next they took a silky scarf and ran over her nipples. "How does that feel?" Jonay asked. "Really nice" said Amy. "I never knew anything could feel so good." Next Theresa found a feather and played it over one nipple while Jonay found a soft rabbit skin to run over the other one. Amy could feel a tightening in her groin and wasn't sure what they were doing to her, but she didn't want them to stop. Next Theresa and Jonay started rubbing an ice cube over her hardened nipples. It was so cold it was almost painful, but incredible. Her nipples hardened even more. Next Theresa and Jonay started alternating the ice cubes and their mouths. The extreme from the ice cold to the hot moisture of their mouths was so intense. "See what you have been missing" Theresa said. "Oh my gosh! I had no idea they could feel that way." Amy said. "Put just your shirt on with nothing under it for the rest of the say and see how they feel tonight". Theresa told her. Amy put her shirt on and could feel her nipples rub against the cotton of the shirt. They were still hard and a little tender, but it still felt really good. She went outside and went to the library. She felt like everyone could see right through her shirt and know that her nipples were hard. It was hard for her to concentrate on her studies that afternoon. She quickly grabbed a sandwich and then went back to the dorm room. Theresa and Jonay were talking together and stopped when she came in. "How did it feel?" they asked. "Very different, I felt like everyone was looking at me." Amy said. "Is that so bad?" Theresa asked. "You are very attractive, people should look at you." "Is that what it feels like when a guy touches you?" Amy asked. "I didn't know it would feel so exciting." She said. "Haven't you ever touched yourself?" Jonay asked. "No, I was told it was a bad thing to do." Amy said. Jonay and Theresa exchanged looks. "So you have never touched yourself between your legs either?" Theresa asked. Amy looked shocked. "No, isn't that a bad place to touch?" Jonay and Theresa looked at her and Theresa said "It's the best place to touch yourself." Amy didn't look too sure. "Do you want us to show you how like we did with your breasts?" Theresa asked. Amy wasn't sure she wanted that, but the experience with her breasts had been incredible and both girls were so nice and so sure of themselves. She wanted to be more like them. "We can start with your breasts again, if you want." Theresa said. Amy remembered back to that morning and how good it had felt. "Okay" she said. She pulled her shirt off and laid down on her bed. Both Theresa and Jonay started stroking her breasts and nipples. "Wait" Amy said. "Can I feel yours?" she asked. Jonay and Theresa looked at each other and shrugged and took off their tops and bras. "You have such fancy bras" Amy said. "We need to take you shopping too." Theresa laughed. Jonays dark nipples were a big contrast to her honey colored skin. They were really large. Amy reached out to touch hers first and ran her fingers lightly over her nipples, afraid to hurt her. "Don't worry about hurting me, I can take a lot of pressure." Jonay said. Amy pulled a little bit on the one and Jonay said "pull harder." Amy pulled a little harder and then pinched it. "That's better" Jonay said. Theresa's nipples were bright red against her pale skin and smaller than Jonay's but her breasts were much larger. "Are they heavy" Amy asked her, as she reached over and lifted one up. "Not to me" Theresa said. Jonay had leaned over and started sucking hard on Amy's nipple. "Mmmm, that is so good." Amy said. Theresa leaned her breast over to Amy's mouth and said "try it". Amy opened her mouth and first ran her tongue over Theresa's nipple. The texture was different than she thought it would be. She closed her mouth around it and sucked and twirled her tongue around it. "Oh you are good" Theresa said. It was exciting to know she could make another girl feel good about her nipples. It had always been drilled into her head that they were evil and not to be seen or touched, much less licked and sucked. Soon she was feeling a twitch between her legs. Jonay and Theresa glanced at each other and Theresa undid Amy's jeans. Then they both pulled them off. They giggled when they saw her plain white panties. "We definitely need to go shopping" they said. They pulled her panties off and Amy felt really awkward. "Don't worry, we won't hurt you." Jonay said. Jonay went and got a hand mirror and pulled Amy's legs apart. "Here take a look first" she said. Amy could see her hair and her pussy in the mirror. She had never looked at it before and it looked complicated. Theresa ran her finger around the outside edges. These are your outer lips and they are sensitive but can take a lot of pressure. She pinched them to prove her point. It didn't hurt at all, but felt good. Amy was surprised. Nest Theresa ran her fingers along the inside lips. They were moist. She stuck her finger inside and got it moist and the se ran her finger up near the top and said "This is the most important part – your clit". "Why is it important?" Amy asked. "It's the most sensitive." Theresa said. She started to rub it and Amy experienced a feeling she had never felt before. Next, Theresa leaned down and ran her tongue around all the places she had run her fingers. Amy thought she was going to fly off the bed. The sensations going through her body were incredible. "Oh my god!" she cried out. Theresa and Jonay were enjoying giving her pleasure she had never had before. Jonay pulled and pinched her nipples while Theresa continued licking her pussy. Soon the orgasm hit and Amy was almost screaming. After it subsided she asked why her parents would tell her it was so bad when it felt so good. "Your parents are messed up" Theresa said. "Are all girls the same down there?" Amy asked. She was incredibly curious now. Theresa and Jonay took off their clothes. First Amy looked between Jonay's legs. Her pubic hair was very dark and super curly. Her lips were as dark as her nipples and were thicker than Amy's were. "Do you want to taste it?" Jonay asked. "I don't know," Amy replied. She touched the outer lips and then ran her fingers around the inside. Jonay pushed Amy's fingers inside her pussy and Amy could not believe how wet it was. She could feel the muscles contracting. She pulled her fingers out and looked over to Theresa laying next to her. Theresa had spread her legs and was feeling her pussy with her fingers. "Do you touch yourself a lot?" asked Amy. "Yes, Quite a bit. Especially at night, when I can't sleep." Theresa replied. Theresa's pubic hair was a little darker than her hair on her head. Her pussy was red and moist against her pale skin. Amy touched her to see how hers felt. It seemed a bit smoother than Jonay's. "Give it a lick" Theresa said. Amy gave it a tentative lick and could smell her female smell. She then leaned over and licked Jonay's. It smelled a little stronger, but not a bad smell. It was kind of intoxicating. "Don't tease us." Theresa said. "I can't lick you both." Amy said. Theresa said she would lick Jonay if Amy licked her. She and Jonay had already pleased each other before. Amy leaned down into Theresa while Jonay climbed on top of Theresa. Amy slowly licked around the edges and then tried to find the spot that Theresa had found on her. She felt something small and hard and sucked on it. "Oh, that is the spot!" Theresa cried out. Amy was surprised. She swirled her tongue around it and sucked some more. "Suck harder" Theresa cried out. Amy could hear Theresa sucking on Jonay and Jonay was breathing hard. Soon Theresa's body was tensing up and she started to cry out. Amy saw her put her fingers in Jonay since she was breathing so hard she couldn't lick anymore. Amy put her fingers inside Theresa also and Theresa cried out in ecstasy. "Oh my God!" "Don't stop!" Theresa yelled. Amy kept sucking and pushing her fingers in and out. Theresa's body shook with the orgasm at the same time as Jonay's. The two of them collapsed on the bed. "Was I good?" Amy asked. "You were incredible" Theresa said. "Does it feel different with a boy?" Amy asked. "Oh, absolutely" Theresa and Jonay both replied. "Have you seen any cute guys?" Theresa asked. "Well, there is one in my English class, his name is Kenny Jones and he is really nice to me." Amy said. Theresa and Jonay both knew who he was. They also knew that he would be a willing partner and gentle with her. They made a phone call and asked him to come to their room the next night. "We have to go shopping first thing in the morning." Theresa said. They went to bed early and got up the next day and headed to the mall. They went to the lingerie store and showed her all the different styles and colors and materials of the panties and bras available. Amy had no idea there were so many different kinds. It was pretty confusing. They sent her to the dressing room with a handful of bras and had her try some on. She found some that really made her breasts look full even though they were small. She found some panties to match and they went to another store to find some flattering slacks and pretty tops. When they got back to the dorm room Theresa and Jonay had her change and they fixed her hair and put makeup on her. They didn't put too much on though, just enough to accentuate her features. She looked stunning and Amy turned and looked in the mirror and couldn't believe it. "I am so glad I came to college! I am learning so much more than I thought I would!" Amy laughed. Theresa and Jonay got ready to leave and Amy started to get nervous. "I wish you could stay" Amy said. "Well, Kenny might not mind, but not this time" Theresa said. "You will be fine. Just remember how it felt with us and it will be even better with him" Jonay said. A few minutes after they left, Kenny knocked on the door. Amy let him in and offered him some wine like Theresa said to. They both sat down on her bed with the glasses of wine and he asked her a few personal questions. They talked for awhile and he turned on her stereo and turned off all the lights except for one. He sat back down next to her and leaned over and kissed her lips. His mouth was warm and moist and soft. He worked his tongue gently into her mouth and explored all around with it. He really tasted good and smelled good. Soon their tongues were swirling with each other and she felt his hand move up her back and then around the front to her beast. She relaxed remembering how the girls had made her feel. He reached under her blouse and undid her bra. His hand stroked her breast and then her nipple. He pinched and pulled on her nipple and it felt incredible to her. She stopped kissing to take a deep breath. He looked into her blue eyes and said she was beautiful. She had never been told that before. He slowly undid her blouse and took it off and then removed her bra. Your breasts are incredible he said and leaned down and started licking her nipple. It was so hard and so sensitive she thought she was going to cum right then. He pulled his shirt off and pulled her against him. His chest had soft silky hair on it and felt really nice against her skin. He then undid her pants and pulled them off. He admired her pretty silky panties. He said they made him excited. He stroked her pussy through the panties and could feel her getting wet. He pulled his pants off and then his boxers. Her eyes widened with surprise when she saw his large cock. He knew she hadn't been with a guy before since Theresa and Jonay had told him, but she looked pretty scared. "It's okay." He said. "I won't hurt you." "Here touch it." He said. She reached out and felt it. It was hard and warm and moved when she touched it. He showed her how to wrap her hand around it and slide it up and down on him. Then he showed her how to reach down around his balls and lightly squeeze them. Then he pulled her panties off and spread her legs to look at her pussy. "Your pussy is so beautiful" He said. "Please touch it" She said. She couldn't wait. He ran his fingers around it and inside it. She was so wet it really turned him on. He knew he would have to control himself. Gently he leaned down and licked her. He sucked gently on her clit and she moaned out loud. "I think you are ready." He told her. He started to gently enter her. She was so tight he thought it would not go in. He pushed more and then all of sudden it slid right in. "Oh" she cried out. "It kind of hurts" she said. He held still and told her to relax. Slowly she did and she could feel how much he filled her up. Slowly he pulled out a little and slid back in. The pressure against her clit got her excited again. Slowly her hips rose up to meet him and he pushed in harder. Soon they were going harder and harder against each other. She started to breathe really hard and he knew she was close. He was so close also and couldn't wait anymore. They both exploded together. He couldn't believe how good she had been for being a virgin. She was surprised it felt so good. "That was amazing" She said. "I had no idea it would feel that way. When the Jonay and Theresa touched and licked me it was so different." Amy said. Kenny had a surprised look in his eyes. The girls hadn't told him that part. "They licked you?" He asked. "Oh yes, they showed me how to touch myself and then Theresa licked me and made me cum." "Then I licked her while she licked Jonay. I actually made her cum too and it was exciting." Amy said. "I can imagine." Kenny said. His mind was racing with the images she was creating. He knew he would be coming to this dorm room more. They relaxed and then he got a washcloth and helped her clean up and get dressed. They talked some more and he said he needed to leave. "When will you be back?" she asked. "When would you like me to come back?" He asked. "How about next weekend? I will fix dinner and you can hang out with the three of us." She said. "I would love that!" He replied thinking what an exciting evening that could turn out to be. Amy's First Time Author's note: I used these characters already in "Amy's Evolution". I loved them so much that I wrote a different plot line here with Amy losing her virginity in a bedroom and not a gym. The story is all new after the first page or so of exposition. I really take my time with this one, and I hope you will enjoy the journey with our Amy. Please read and comment! ***** I believe martial arts saved my life. Brazilian Jiu Jitsu (BJJ) to be specific. It saved me from obesity, low self-esteem, and it even stopped a rape. I love myself, both inside and out. But it took a while for me to get here. I grew up fat. The problem started around sixth grade and got worse through the cruel years of junior high and high school. It killed my confidence, and that in turn made me more shy, so I didn't have much personality to compensate for the fat rolls. It was a vicious negative feedback loop. Making matters worse for my self-esteem, I went through high school with newly divorced parents. I was a pawn in their war and missed out on a lot of parental nurturing and mentoring. I never got asked out in high school. Not once. I was a natural red head, but instead of embracing my uniqueness like I should have, I was embarrassed. I thought the fair skin, freckles, and orange hair just made me uglier. The extra tonnage seemed to hit me in all the wrong places, quickly giving me a double chin and hiding any semblance of a waist. The only thing I had going for me was a large rack. But my overweight condition just made them seem obnoxious to me. Instead of perky, proportionate breasts, I had jugs. I felt like a heifer with over-sized udders and back pain. The boys must have seen it the same way, because they weren't exactly beating down the door to me. College was better. It was easier to make friends as my peers matured and looked past appearances. I studied hard and got great grades while holding down a part time job, and I began to realize that I was likely going to have a successful career if I continued to apply myself. My self esteem grew, and my personality blossomed. I developed a quick sense of humor and a social life. But I continued to neglect my health. I just had no interest or willpower to work out or eat healthy. I used that as a convenient excuse for why I had lots of guy friends but no lovers by my senior year. The truth was, I didn't even really care. I had zero libido. The urge to study or eat dessert was stronger than the urge to spread my legs. I graduated college a total virgin. I hadn't even kissed a man or tried to give myself my first orgasm. I was fortunate to land a job right away. I moved halfway across the country to Richmond as a 22 year-old, entry-level professional. I worked my ass off the first six months, earning a good reputation and securing my place in the company as a valued employee. But every day I got more frustrated looking in the mirror. It was a lot harder to meet people outside of college. I began to think of things like getting married and having kids. I knew none of that would happen. A victory for me would just be living to forty without having a coronary. But now I had the willpower and the free time to do something about it. I read one of those "think outside the box" self-help books and found some motivation. I tried a few new hobbies that turned out to be minor distractions. The big change came at the Mixed Martial Arts gym I passed on the way to work every day. One day I just decided "what the fuck" and went in. I needed to get in shape, but I knew if I just ran on a treadmill every day like a rodent, I would quickly get bored and stay fat forever. It absolutely sucked for the first month. There were only a few other women there, and I felt like everyone was making fun of me. But I eventually saw that actually these were a great group of folks. They encouraged me. A few of them had been overweight also. So I stuck with it. It was weird to grapple and go home drenched in the sweat of twenty men, but I got used to it. It was hell. I was choked, arm-locked, had my face ground in the mat, and had people lay on top of me and suffocate me with pressure. I was in every way made to feel helpless as I learned. It steadily got better as I learned to move to lessen the pressure of a large man on my body. Occasionally I even got the upper hand. This was the most attention I'd gotten from men, even though it wasn't exactly in a romantic way. Even if the men I trained with weren't interested in me sexually, it was fun to occasionally have them between my legs for the first time. I'm sure they didn't exactly mind being pressed against my large rack. My areolae and nipples were on the large side also, and I had a bad problem of nipping out that I'm sure the guys noticed. After five minutes of exercise, my fair-skinned face flushed red, sweat coated my body, and my nipples got hard and poked through any brand of bra on the planet. I noticed after a few weeks that my jeans were looser and my face wasn't as bloated. Once I started seeing positive changes, it was easy to find motivation to make more changes and accelerate the process. I started eating better and smiling more. I bought more fashionable clothes. I started growing out my short, bland hairstyle. I lifted weights at the small gym in our office building to supplement the jiu-jitsu. I jogged on weekends. People at work and at church saw the changes and encouraged me. I continued to train, and the classes just got more fun. I began to occasionally submit some newer men in training with chokes or joint locks. I felt empowered and was having a great time. After about 30 pounds and eight months of training, I think I was much better looking but still too chunky. I was barely in that window where men who liked a lot of curves might not think I was too fat to make it a deal breaker. I got asked out. My first real date wasn't a great one, probably due to my nerves, but it felt awesome to have a guy finally show interest. I setup a profile on a dating website and went out on a few more first dates. But I just couldn't meet the right guy to move things to the next level. The guys looking for a relationship were picky, and I wasn't interested in the guys I knew were looking for something a little more short-term. But I sure did enjoy finally occasionally getting kissed goodnight, and I became more confident around men. After a few months of this, I finally got a call back from a guy I actually wanted a second date with. I got careless and accepted an invite to his house despite not really knowing him well or doing a background check on him. Everything seemed great. He was good-looking, charming, and a great cook. I had never been pampered before like this, and his efforts made me feel like a queen and clouded my judgment. He had game and easily primed me with a few drinks before moving me to the couch to begin a make-out session. This was my first time getting tongue. So far, so good. It was fun, and he was a good kisser. I let him fondle my breasts over my shirt. Soon my top was off. I knew where this was headed, but I wasn't ready to go all the way. I put on the brakes just as he shoved down his pants and underwear in a blink of an eye, giving me my first look at a real penis in the flesh. He got angry, first joking around, then getting pushy. Before I knew it, he was lying on top of me. I felt his erection poking at my inner thigh as he took just enough weight off me to be able to reach under and fumble with the button on my jeans. The rest was a blur. Nobody had tried to rape me before, but I certainly was no stranger to feeling a man's heavier weight on me. I was almost a blue belt in BJJ at this point, and at least had a chance of defending myself against a strong man. I was taller and stronger than the average woman too, which helped. I was confused for a few seconds. Was this really happening? Could I be misunderstanding something and this was just some kind of passionate play, and was I supposed to go along? No. I was inexperienced, but not stupid. I remember staying calm and asking several times for him to get off, saying "no" more than once. He didn't comply. By now my button was undone and the zipper down. The sight of my panties seemed to encourage him more. He was calling me pet names and smiling, as if he wasn't trying to force himself on me. I wrapped him up between my legs in the guard position, easy to do since he was trying to force my legs apart anyway. I scooted my hips to the side to go for an arm lock, forgetting I was on a couch. The movement pushed him off the couch and me with him. I scrambled to get on top of him, then quickly wrapped up his arm and fell to the side. I lifted my hips, and with the force of my entire body pressing up against just his weak elbow joint, I easily broke his arm. I felt a weird satisfaction as his elbow made an awful crunching sound. I gave him a few elbows to the face and opened a cut above his right eye for good measure, then retrieved my top and bra and left his apartment amid a sea of his obscenities and, oddly, apologies. We never spoke again. This was also the first and last time I ever drove home with too much alcohol in me. I felt horrible for putting others at risk, and I considered myself lucky when I arrived home in one piece. That was a valuable lesson that made me lose interest in dating for a bit, now as a 23 year-old virgin. But at the same time I was becoming curious and impatient for my first sexual experience and didn't want to stay sidelined for long. I had no religious hangups, although I sometimes wished I did. I did attend church after all. Then I would have the best excuse of all for my puritanism, and maybe be a better person in the process. But I didn't want to wait until I was married to get laid, especially since I wasn't sure marriage would ever happen anyway. I think the aggressive nature of almost-daily BJJ training changed my hormones a bit and amped up my libido. I was also far healthier, was not embarrassed by my body as much, and had higher self-esteem, which all worked together to increase my sex drive. Twenty minutes of exploring my curiosity on the Internet along with some experimental diddling that yielded my first orgasm got me hooked on porn. I quickly developed a daily masturbation habit. Pleasing myself was so much fun that I couldn't believe I had waited this long. I did that for a few months after the almost-rape incident. The weight continued to come off, and by now I felt I had about 20 pounds to go to arrive at my ideal weight. I had a clearly defined waist and just needed to get rid of some pooch in the stomach, fat around the thighs, and an inconvenient double chin. I didn't look that bad anymore from behind. I was pleased with the shape of the cheekbones and other facial features that had emerged from my chubby face. My breasts stayed very large, and I began to wear clothes that showed some cleavage. I was definitely getting a lot more looks and compliments now, and I could look in the mirror and humbly tell myself that I was looking at the beginnings of a beautiful woman. This is when Claudia and I started to spend more time together. Claudia was one of the few other women that I trained with. She started a few months after me and was therefore always at about the same skill level as me. We were the same age and both professionals, but that's where the similarities ended. She was completely ripped from the moment she sauntered into the gym, because she was already a serious kickboxer and just wanted to work on her grappling. She was a gorgeous, outgoing Latina with a very warm and genuine personality. I still wasn't dating much after the incident. Almost being raped on your first ever second date was kind of demoralizing. I wasn't avoiding men, but I had cut down my prospects a lot when I deactivated my online profile. I wanted more friends to hang out with to fill this free time, so I asked her over to watch a movie and eat dinner. We quickly became great friends outside the gym. I don't think there is anyone on earth besides Claudia that could have gelled with me so well as to instigate the events that came to pass. She was beautiful inside and out and was one of the most interesting people I'd ever met. She had traveled a ton and was fluent in four languages. Unlike me, she dated a lot and put her body to use. As we slowly became best friends, I got a true picture of how slutty she really was. She loved sex and had no desire to tie herself down yet. This translated to a lot of well-satisfied men who later had their hearts broken. I slowly began to date again, and we shared stories. Mine were always with a little less detail and focused more on bad first dates. She knew I was more reserved, but I never told her I was still a virgin. We soon had standing hangouts together on Friday nights if we didn't have dates. It was always at my place since it was more convenient to our work and the gym, and it involved a nice dinner and a movie rental. We'd usually watch a chick flick over a few drinks and make fun of the characters. I looked forward to this night starting on Monday of each week, and I secretly began turning down Friday night dates so we could be together. I think Claudia felt the same way, but she enjoyed a variety of dick so much that she didn't turn down her dates. But she often came over for a night cap afterward if she didn't shack up with whatever lover had her interest. We were both night owls, and she could count on me still being up at midnight and willing to watch a movie and chat. I was attracted to Claudia. Ever since elementary school I can also remember being attracted to women, but I never told a soul. It was rare and subtle compared with my attraction for men, but with the right combination of personality and gorgeous looks, I would notice a girl and think, "Yeah, I might want to kiss her." For my tastes, Claudia was easily the most beautiful woman in the world. She had long, dark black hair. Her face was fair and freckled like mine, but I was a Midwestern red head while she was an exotic Latina with Spanish roots. We were both relatively tall. I was about 5'10" with Claudia maybe an inch shorter. Claudia wore spandex a lot while grappling, and her muscles rippling on her butt cheeks often had a mesmerizing effect on me. I think she brought the printed leggings fad to Richmond, and she sure rocked the look. She had a tiny waist, a flat stomach, and a nice chest that was a lot smaller than mine but would still fill my hand nicely. After months of grappling with her, I knew her breast size well since I was often pressing against them and accidentally groping her. She also had impeccable style with clothes, and I never knew which version of her I liked more: the spandex-clad, sweaty version, or the made up, elegant version. Both were so attractive and effortlessly seductive. Some might find her too skinny since she had low body fat, but I thought she was perfect. Her butt was tiny but full, and the muscles gave it enough mass and curves to look great with her slim waist. I have no idea if Claudia was attracted to me in that way, whatever "that way" even meant. I just loved being around her and might have liked to kiss and see how that made me feel. Claudia and I never talked about it. Things never got weird even as we grew closer. Cuddling together under a blanket during our movie night became standard. I was grateful that my small couch, which was really more of a love seat, forced this physical closeness. We could talk about anything, and after a few drinks it always turned to sex. Claudia loved to talk, so she didn't really notice that I wasn't sharing as much. I think this is why an enormously popular, outgoing woman loved to hang out with little old me on Friday nights. She could be herself and talk about anything in a judgment-free zone, and she had a patient, captive audience. I kept my own details vague enough to fake that I had any experience without lying. If she had asked if I was a virgin, I would have fessed up. But she never asked, and the longer I waited to tell, the harder it was to admit. I'll even admit I kind of enjoyed waiting for her to figure it out, and to this day I wonder if she knew all along. After a few months of hanging out, we began a tradition of watching a little porn at the end of the night. Claudia had busted me and found a bit of it on my computer one night, and we ended up watching some of it together. We both thought it was cool to watch in small doses for a good laugh, and the fact that we typically had a few drinks in us helped. We drank responsibly. It only took a few to get us more than tipsy, and she sometimes crashed on my couch. I usually drank only on Friday nights. Her "walk of shame" consisted of putting on workout clothes early in the morning and going straight to the gym. That seemed very respectable to me. We began a rotation where one of us would pick the movie, and the other would find the right porn to look at if we got to that point. It was a fun game, and Claudia and I continued to get to know each other and grow close as weeks passed. We enjoyed talking about which guy we thought would be the best guy to screw and why, and then we'd make fun of the girls for various reasons. It was obvious that Claudia evaluated the whole man, but the most heavily weighted variable was how much he was packing. She was definitely a size queen. Since the gym was our only common group of friends, we also talked about the men there. The only guy either of us wanted to fuck was the coach. He was about fifteen years older and married with a few kids, so he was off-limits. One night I decided to be a little risque, and after I ensured Claudia had sufficient red wine lubrication in her, I put on a lesbian scene with a gorgeous porn star named Andie Valentino. "Wow, we haven't watched one of these before," Claudia commented. We were cuddled on the couch, her hand on my knee. I don't know on what planet casual, non-sexual female contact among close friends like this would be considered normal, but Claudia and I were just like that now. "I like this girl. She's the only porn star I would kiss," I said. Andie only did lesbian scenes. The brunette had a gorgeous face and natural breasts that rivaled my own in size. She was famous for her defining characteristic of over-sized pussy lips. I also had big labia and was a little self-conscious about them, so seeing her on screen looking beautiful made me feel beautiful about my own body. I just wished I had her ripped physique to go with that chest. God bless Claudia, she read my mind. "Oh wow, have you kissed a girl before, Amy? I wouldn't have guessed," she teased. "No, never. You?" She shook her head no. "Nobody asked me before," she said. I looked out of the corner of my eye and she was smiling at me, waiting. And just like that, it happened that easily. We leaned in. Our lips connected, just for a second longer than a peck, then we parted. I stared into her eyes for a second. I wish I could say our first kiss was amazing and we tore our clothes off immediately, but it was nothing like that. It was awkward, and there was no momentum to continue the kiss or try something else sexual. "Eh, I don't know," I teased. "I do think you're hotter than all the porn stars we watch, but really, that did nothing for me." A compliment with a dismissal in the same sentence seemed appropriate. "Yeah, I expected more from you, too," she fired back. "I'm so disappointed," I added, joking around. But I was still crushed, and I should have known we couldn't be intimate like this all of a sudden. Perhaps it didn't happen like this in the real world; we had to ease into it. I was grateful I had a partner both willing to try and able to make jokes about it to smooth things over after it bombed. But I wasn't turned off, rather it was just awkward. She was still gorgeous, and I knew I wanted to do it again. Amy's First Time Claudia was ready to leave shortly thereafter. She had stopped drinking and sobered up since she was running a 5k race the next day. I grabbed her arm on the way out to go for our usual close embrace. "Let's do it one more time just for fun," I said. She was leaving, so there was less pressure. Our full lips melted together softly, and this time they lingered. I felt her breath, sweet and feminine. It was different than a man's kiss, or at least the few I'd smooched before. Both of us were soft and unhurried. She paused after a few seconds and came up for air. "One more time, with some tongue," she said. This time our mouths opened and her tongue slid into my mouth. I massaged it gently with my tongue before thrusting into her mouth to return the favor. After a few more slippery exchanges, we were done. I wanted more, but I sensed I shouldn't push my luck yet. "Better," I said. "I would say it has potential. Is this going to make it weird and ruin our friendship?" No way, I thought. "Nothing will ever ruin our friendship," I said. She smiled. "I don't plan on going any further anyway," I said. "My panties are a little damp, I admit it. But I have my limits." I cringed, realizing I had said too much. No filter! Bad Amy! But she laughed, probably not realizing I was dead serious about my arousal. "But I could get used to a kiss goodnight from you every time you walk out my door." "Deal." Even though the kissing had been slightly uncomfortable for us both, I was still glad we did it. At this point in my life, anything out of character I did was a blessing and symbolic of my newly improved self. For the first time that night, instead of thinking about men when I masturbated, I thought about Claudia. I took my time, bringing myself close to orgasm several times before backing off, building the anticipation a lot before finally pulling the trigger. I went through several lovemaking scenarios in my imagination as I stroked my clit, not really sure how a real-world session with Claudia would actually play out in bed. How do women do it? My knowledge came from porn, and I knew that was at least partly misleading. In the end, just imagining Claudia kissing me and touching me was all it took to get off. My desire for her was part physical for sure. I thought of her beautiful eyes and hair, her kind face, her shapely legs. I thought about her nice ass in tight spandex, and I thought about how good it felt when I was all sweaty laying on top of her in the gym. But it was also the emotional connection that aroused me. Unlike all the men that previously joined me in my mind for a heavy masturbation session, Claudia was the only person that I truly loved, trusted, cared about, and was attracted to in real life. This intimacy enabled me to really open up to her as a lover, sadly only in my imagination. Claudia and I continued our Friday night "dates", and I got that kiss every time. I wondered what people would think when they saw us at the gym training hard, grappling with the men and each other, if they knew what we did when we were alone. She stayed over more often now on those Friday nights. We were comfortable enough around each other, and my place felt like home to her. One night she got a little drunker than me and fell asleep talking to me in my bed. That turned into her sleeping in my bed from then on if she stayed. I only had a one-bedroom apartment, and my tiny couch that I had bought used really sucked to sleep on unless you were super drunk. The second time she did this, my air conditioner was crapping out, and we stayed up really late. She came out of the bathroom and crashed on her stomach on top of my sheets in only her panties and bra. I'm glad her face was in the pillow, or she would have seen me staring. Her butt was simply flawless. "Nice tramp stamp," I teased her. She had a very cool looking design on the small of her back with edgy black and red lines. I had only glimpsed part of it before. "Cute butt too," I said and patted her tiny behind over her black panties. It wasn't really rock hard since she was relaxed, but I could still tell that was muscle there, and I was pushing around just enough fat to make her feminine with none to spare. Claudia looked up and smiled at me. "Good night," she said and gave me my kiss, then she was out. I wanted to make out with her and see what happened, but I was too scared. Looking back, doing nothing was the right thing. She wasn't ready. But I sure was. That night represented a milestone for me as I leaned over and tried to peer between her slightly spread legs. There was no doubt now. I wasn't just attracted to Claudia with a desire to kiss her and cuddle. I wanted to take her panties off and make love to her. It was oddly liberating to know for sure what I wanted, even though I had no idea how to go about it. My overall sexual libido for men was growing also, so I felt secure in my "straightness" even as I became more enthralled with Claudia. From that point on, any time she stayed, she slept in her panties next to me on the bed. I always had on pajamas with a bra to keep my breasts in check. I was such a prude. I just hoped Claudia went to sleep with her panties a little moist also. I didn't know how to take the next step. If she rejected me, it would risk ending our friendship. So I did nothing. Soon Claudia left for a couple weeks. Her grandmother in Mexico was ill, and Claudia was beside her bed when she passed. The two were very close since her mom had married very young, and her grandmother had played such a large part in raising her. We talked every night while she was there, and we hung out more than usual the first week she returned. At this point we really were best friends, and I would have trusted her with anything. Claudia quickly returned to her cheerful self and her never-ending quest for cock. A couple Fridays later she canceled movie night with me, then called me at 11PM and said she'd be over in five minutes. I was on my second glass of wine already and wearing pajamas, and when Claudia showed up, she was clearly way ahead of me. She seemed really out of character with a skirt and white blouse. There was no cleavage showing, and the skirt wasn't skin tight and short enough to show perfectly toned thigh muscles. She looked like an adorable Catholic schoolgirl. Her hair was messy. I had a feeling she had been bedded already, perhaps in some kind of amazing role-playing adventure that involved her hair in pigtails. I normally wore a bra around Claudia since I was self-conscious about my heaving mammaries jutting out there so much, but I thought the last minute notification she had given me provided me the perfect excuse to go natural. I was busting the seams of my pajama top and nipping through nicely, but Claudia didn't even glance at them. "I went to Damon's," she said as she gave me a quick hug before passing me into the living area. I was mildly annoyed, thinking to myself, Shouldn't she be looking at my tits? "Booty call? You're going to break his heart again, you know. How did you get here?" "He came over to my place to fuck me, then I made him drop me off here. I made it clear I just needed his size and a good lay," she joked. "He accepted my terms. I might be a little sore tomorrow." I laughed. I had never heard Claudia use the F-word outside my apartment, but here she was completely authentic and held nothing back. She and I had talked about Damon before. She dated him for about a month during the previous year. His defining characteristic was the largest and most reliable cock she had been with. I had no idea about his personality, age, or what he did for a living. Someone that didn't know her well might assume she had low self-esteem due to her promiscuity. I knew better. Claudia just loved to fuck and went after what she wanted. But tonight was different. It was too soon after a personal tragedy, and I thought I detected a sadness or desperation hidden in her expression. Plus she was a little drunk, and she seemed to be a bit more aggressive. She set her purse on the counter, then opened it and got out a breath mint. She normally carried a smaller handbag, and when I peered nonchalantly into this bag, I knew why. "What's in the bag?" I asked her playfully. Enough of the shape was showing to identify a blue dildo. For half a second, she seemed flustered, but she got her composure fast. She pulled it out and handed it to me. I had never seen one, but I knew immediately what it was and how to use it. It was a double-ended dildo, but it was in an "L" shape, and the smaller end had a bulb end and was designed to go into the giver's pussy and remain firmly in place, while the larger end that resembled a real penis was obviously to fuck the receiver. "Have you seen one before?" "No, but I can tell what it's for." My heart was a beating a little faster now, and I was nervous. Was she trying to take it to the next level with me? "Is this for.." I didn't know how to finish. Do you really want to fuck me with this? "Damon gets kinky sometimes." I felt stupid. I was thinking she was going to try to seduce me, and really it was for her fuck buddy. She had even mentioned this kind of role playing before, and she had just been to see Damon. I wasn't thinking clearly. Then I realize I was holding something that had just been in a man's ass. I gave a grossed-out face and handed it back to her. "I didn't use it tonight, silly. It's very clean. I carry it, you know, just in case." "Do you need a harness?" I asked. "Doesn't it fall out?" "No, but it takes some practice for sure. I have good muscle tone down there now and can grip it well. You'd probably need to strap it on, though." I laughed and went with the joke. "I do have a loose pussy. I'd prefer a little more size if I was on the receiving end for my tastes also," I lied. Claudia continued to blend humor, candor and confidence perfectly to me in private. But something was still definitely off with her tonight. She discussed this kind of stuff before, but she was usually a little more smooth about it. Tonight she seemed more energetic, like she was both drunk and on powerful stimulants or something. I was worried since she was probably depressed due to her grandma's passing, and this was her way of dealing with it. But I wasn't here to judge; I was here to love her. "Do you have any other surprises?" I asked. Claudia sat on the couch, relaxed with her legs slightly spread. "He gave me a cream pie about ten minutes ago," she said slyly. "I felt some of it drip down when I was getting out of his truck. So annoying. This is why I make men pull out." An awkward few seconds went by. "I can't believe I just told you that." "Oh God, girl! Think safety, come on." I was shocked. I knew Claudia did stuff like this, but it was different this time because it had just happened, and she was very graphic with her details. "You know I'm on the pill, and I've known him a while," she said. "Show it to me," I said. I regretted it as soon as I said it. At least, until she did what I asked! This turned out to be the best ice breaker we could have possibly invented. Thank you, man-I-have-never-met called Damon! "Well I'm not wearing any panties anyway," she said casually. Claudia lifted her legs and spread them with her feet on the edge of the couch. She hiked up her skirt on her front side, and sure enough, her pussy was on full display. I must have been staring, frozen. "Well, come closer. I won't bite. You've seen a vagina before." I laughed and complied. "Not yours." The lighting was dim, but standing only a few feet away now, Claudia gave me a great view. She was completely shaved. I enjoyed a full view of her swollen labia, her Hispanic genes giving them a nice dark tint to contrast against her fair skin. Her lips were shiny, like she was aroused or someone had been licking her. But her crack was closed tight, and I didn't see any semen flowing out. "That's a gorgeous pussy, and I would expect nothing less from you," I said and smiled at her. "But it doesn't look inseminated. There's no gape at all, and you're not leaking." I couldn't believe we were having this conversation. It was silly, as I tried to keep the mood light by deliberately sounding like a man who had seen way too much porn. Yet I couldn't look away and stop making stupid jokes. "Let's see if I can push some of it out." She used her legs on the edge of the couch to lift her butt and pull the back side of her skirt further underneath her, always being considerate of other people's stuff. I suppose I didn't want body fluids oozing out on my couch, but if that was the price to pay for a view of her pussy, it was certainly worth it. Claudia smiled and brought her hands to her crotch. I was glad we had seen so much porn together, which oddly made this a little less shocking and awkward. She pulled her lips apart, opening a small hole at the bottom. "There has to be more in there. He always shoots a lot, and it goes in deep. Only with him does it drip out for so long after. Huge cock and huge loads: the two don't always correlate. I was a lucky girl tonight." I saw her abs flex, and the hole at the bottom of that beautiful crack seemed to open more just slightly as her internal muscles fired, then nothing happened for a couple seconds. "There we go," she giggled. I couldn't believe it: semen bubbled up into the tiny hole, then oozed down to where her anus pressed against her skirt. The viscous fluid did not vanish, instead a glob remained at her entrance, with a thin stream coating her perineum downward. This was the first time I had seen real semen. The soft yellow light was dim, so I could barely make out the white tint to the shiny fluid. But there was no doubt as to what it was. I didn't realize that I had continued to move closer, transfixed. I was within arms reach, smiling curiously and looking at her pussy. Then Claudia really shocked me. She ran her finger from her anus to her vagina, clearly getting semen on it, then stuck her tongue out and transferred a generous glob with her finger and pulled it into her mouth. She then put her middle finger back into her vagina to get the glob still perched at her entrance and whatever bit was just inside. She held her finger out to me. "Have a taste, Amy." Curiosity and peer pressure, egged on by the effects of alcohol, instantly won out. Without hesitation, I threw caution to the wind and opened my mouth and sucked down the length of her wet finger, running my tongue around the digit to accept the fluid. Oh my God, I thought to myself. My mouth gave a kissing sound as her finger plopped out. I inhaled, and the unfamiliar taste of semen grew with the strong scent. I knew this was the real deal. I had tasted myself out of curiosity before, and I knew I wasn't tasting my friend. This was all man. I could scarcely believe what I had just done. My first taste of sperm didn't come from a blow job, but instead came from the used vagina of my best friend! The texture was slimy and sticky, and the taste was both sweet but unlike anything I had ever tasted. Surprisingly, It didn't gross me out at all. Claudia and I were looking dreamily into each others eyes, our faces neutral, perhaps in a state of shock. She wiped her crotch with her skirt to remove the excess as she stood, ready to make this even more interesting. She leaned in, and we shared our most intimate kiss thus far. There was lots of aggressive tongue action as our lips pressed together hard. I was getting off big time on the idea that a man's spunk was flavoring our kiss, but we could enjoy it privately. It seemed so naughty and taboo and completely out of character for me, even above the already exotic appeal of kissing a beautiful woman. Our soft moans of pleasure seemed very load without my TV or stereo on. We shared his load for a few minutes as the taste dissipated, then we slowly broke off the kiss. By now we were in a tight embrace and looking into each others eyes again. She was pulling me into her, and I felt my crotch rub against hers through several layers of pesky clothes. "Holy shit," she whispered. "He has a nice taste that's not too overwhelming," I said, as if I had taken enough loads to know the difference. "As do you." We slowly smiled, then we both suddenly burst out laughing. Then she took a step back, and there was a few seconds of silence before reality set in. "You okay with what happened?" Claudia asked. "Is it going to be weird now?" "It's already as weird as it can get, but we're good," I assured her. "I'd almost forgotten what it tasted like, so thanks. But, you are way too manipulative," I accosted her teasingly and poked her in the sternum. "I'm not a bad girl like you. I don't do these things." "Hey, you've been on a lot of first dates lately, so I figured you needed a reminder of what it tasted like." "That's true, but only because I don't do what you do on first dates," I said. If only she knew that was really my first taste at all! Claudia made herself comfortable again on my couch, drink in hand, then she moved the conversation to a more serious tone. "I lied to you," she said. I looked at her inquisitively. "I was feeling low today. I don't know why. You know, sometimes you just can't explain it. I felt depressed because of what happened last month, then I felt slutty and even mean after fucking Damon. Maybe it's time to grow up. Do you think less of me?" She waited a second, then hastily added as if she just realized she might offend me: "None of this has to do with kissing you. I feel very relaxed and not guilty at all with you, even doing what we just did." "Wow, that's the first hint of any insecurity I've ever seen from you," I said. "You're human and not perfect after all." She nodded. "You've said so many nice things to me, building me up as I've lost this weight. Give me two minutes to return the favor." "Okay," she sad as I sat next to her. I moved a bit of her long hair out of her face and stowed it behind her ear, then left my hand affectionately on her shoulder. "One of the things I love about you besides being the best friend I've ever had is that you do everything on your own terms. When you're ready to, you know, not be such a slut and settle down," I said and paused for us both to laugh and release the tension, "you will bring the same love and consideration to a man that you have to me, and you will be a great partner. I love that you go after what you want and don't let anything stop you, putting that great body to use. Plus you are the most beautiful woman I've ever seen, and there's bound to be a lot of men that feel the same way." She just looked at me for a few seconds. "Thanks," she said. Claudia excused herself to my bedroom and the full bath there, presumably to clean up down there a bit. Her abrupt departure made me nervous. I had dropped a few hints to indicate I wanted to deepen our intimacy. I took a sip of wine to cleanse my palate of sperm, although I didn't taste it anymore anyway. I'm not sure why I did what I did next. I was starting my third glass of wine, so I was a bit tipsy, and I had just done something sort of sexual with Claudia to break the ice. I heard the vent to the bathroom and figured I had a few minutes. I pushed my hand down the front of my pajamas. The garment was loose and I wasn't wearing panties, so I had room to work. I parted my big lips easily and ran a finger along the crack. I wasn't surprised at all to find myself so wet already. The fabric between my legs was moist too in a small spot, and I realized with amusing horror that Claudia probably had seen that. She hadn't even put the dildo away. It was sitting on the counter next to her purse. I picked it up and admired it for a few seconds. I thought it was a beautiful work of art, seductive even by itself. I had never used a vibrator or dildo before, so this one piqued my curiosity. I became more aroused as I thought of either end being inside me, enjoying the intimacy it would surely bring between me and my feminine lover. Then I briefly pictured a man bent over with me, the innocent virgin, plowing him from behind, just as Claudia said she had done. To my surprise, this fantasy I'd never tossed around in my head just made me even hornier. I was overcome with a sudden, strong urge to feel it inside me, even if just for a moment. Amy's First Time The short end was slimmer and less intimidating. I took it into my mouth with a nervous look over my shoulder to ensure privacy. With some natural lubrication applied, I brought the dildo under the elastic band of my pajamas, pausing first to rub the bulbous end against my clit. I permitted myself a soft moan, then slid it down my crack until it was seated at my entrance. I parted my legs a little more than shoulder width apart and felt myself open up. The tip slid in easily almost to the widest point. I added gentle pressure and felt an unfamiliar burning. My virginity? Would I have to stretch my hymen to get it inside? It was certainly wider than a single finger from my own hand, which was the biggest thing I had previously inserted. With my brief history of violent sports, I was skeptical my maidenhead would still be an issue. I joined my other hand to help support the dildo, bent over a little more, and was about to plunge it in all the way and get it over with when I heard a voice behind me. "How's the fit?" Claudia asked. Her voice startled me, and I reflexively pulled the dildo back, my pajama bottom snapping back into place, hopefully without exposing myself to her. I giggled with nervous energy, and I knew my face was deep red with guilt. "Don't sneak up on me like that, girl. I didn't even hear you flush." "Of course I flushed. I can't help it if you're off in fantasy land." "I'm so embarrassed," I said meekly. But I felt good. I was close to Claudia and enjoyed joking about this stuff. "I didn't put it in." I could tell Claudia loved catching me in a compromising position. She was comfortable in any social situation, and she enjoyed toying harmlessly with me. She held her hand out with a mischievous smile, and I handed her the dildo. "I prefer to do the driving," she said. She reached under her skirt, her panties still off apparently, and spread her legs slightly. She sighed softly, and I knew she had inserted the dildo. I wished I could look underneath her skirt and see the toy protruding from her beautiful pussy, her dark lips curled around it. Apparently I was leaning my head to the side while I thought that. "No peeking," she said. I played along. "Well, is it in?" She answered by turning to the side. Her miniskirt was being lifted by the fake penis, but the fabric was long enough to drape over it and conceal what I needed to see. "How do I look?" she asked. The way the dildo propped up her skirt indicated she had inserted the smaller end, making her the "giver" in this impending sex act. "Evil," I said. "And gorgeous," I admitted. "I don't think you can be trusted with a tool like that." She sauntered over to me. I was standing by the counter by the kitchen where my bar stools would be if I had any. She grabbed me by the shoulders and turned me to face the counter. "What are you doing?" I asked, as if I didn't know the obvious answer. I felt her close behind me, her hot breath on my neck. Then she kissed me there, and I felt the dildo poke my right butt cheek. I emitted something resembling a cross between a moan and a laugh as goose bumps flared up on my neck from the kiss, and erotic energy spread throughout my body. "Spread your legs a bit," she said. "No," I said playfully. "Come on, humor me just for a second." she encouraged me, using one of her feet to move my left one over. She was successful. I really wanted her to, after all. "Arch your butt back just a bit." While I hesitated, suddenly she yanked my loose pajama bottom down to my knees. "Oh God, Claudia, I don't know," I said. Her face had moved slightly beside me now, so I could see her out of the corner of my eye. Her arms were wrapped around me. "I'm impressed. Nice butt, Amy. I'm going to take you from behind," she said. "Thank you, about my ass. I mean, no, I don't know about this," I said, but I was smiling like crazy, and I arched my back even more to open myself up, just as she had requested. My breasts pressed against the high counter now through my skimpy pajama top, and my head leaned forward. In seconds, Claudia had put me in an impromptu modified standing doggie pose, bare-assed and ready to fuck. I looked over my shoulder. I still couldn't see the phallus, because I was bent over slightly, and the skirt she was wearing covered it from my view. For a few moments she just held me, her head against my shoulder. "I've never used one on a woman. We'll give it a try. Don't be a tease. It's what you want, too," she said. She said it like a statement of fact, not as a question. "Yes, I mean, maybe, I don't know. Shit," I said. The head of the dildo was now centered and pressed between my cheeks. My butt-hole was semi-protected since my feet weren't that far apart and my cheeks got in the way. But a bit lower, my pussy was very accessible. I knew my experienced lover would soon find the mark and drive it home. "Oh my God." I laughed nervously. "Are you really going to fuck me?" I was whispering now, my heart thumping. "Yes." "Maybe just a little," I said. Shit, that doesn't even make any sense, I thought. Make a real decision. She just laughed. "Just a little," she echoed, then said something delightfully sexy to me in Spanish. "Huh?" "It's a Portuguese expression. I'll explain when I find your cunny in this forest you have here." In a fleeting bit of confidence, I moved my left leg over more and stuck my butt back even more. "Come on, Claudia. It's a big target," I teased back. She'd have no trouble finding it now. I felt my thigh gap widen and my butt cheeks part more. Folds of flesh that had been stuck together separated, and fresh air circulated around newly exposed pink flesh. My flower was open and ready to receive. She expertly angled the dildo down a bit and found the big lips I presented to her, jutting obscenely out of my orange bush. Despite the awkward position, just as I expected, Claudia easily found the entrance to my virgin pussy. "Yep, I got you," she said. There was already a steady forward pressure, and I could tell from the way it tugged at my flesh that my right pussy lip was folded over my entrance. She repeated her sexy words in Portuguese, then gave the penis a slight jiggle to part the ample lips and moisten the head. "Roughly translated, where the head of the penis goes, the rest will follow." She gently nudged it forward, unimpeded. I panicked just as she began to penetrate me. I wanted her inside me so much, but I just couldn't do it. "Wait, no," I said as I pushed my hips forward to evade impalement. I pulled up my pajamas then spun around. Claudia's expression changed. Was she disappointed or embarrassed? "Okay," she said, and took the dildo out and put it in her purse this time. I noticed the light reflecting off the tip of the dildo, now wet with my lubrication. "We don't have to, I mean I thought you were interested and wanted to have some fun, nothing serious. It turns you on, right? You gave me all the signals." I took a few seconds to work things out in my head, and of course Claudia took that as further signs of rejection. "Yes, it would be, it's just... I'm sorry." What I wanted to say was that I had never had sex before, and that being impulsive was a huge turn on, but I was a little chicken and wanted to take our time. I was greedy, and I didn't want to share my big night as I shed my virginity with another lover she had taken earlier that night. I wanted to clean up and be fresh down there and show off and let her adore my body for a while before she made love to me. I wanted to take my time and adore her body also. I wanted to be with her when she was more grounded, not a manic drunk that made me feel like I was at a drunken sorority sleepover. I wanted to scream for her to come back tomorrow and we'd make it special. But mostly, I just wanted to say I loved her and she meant so much to me. But nothing came out. She was giving me exactly what I had been dreaming about for weeks, yet I had to reject her. "I'm going to go," she said, and in less than a minute she was at the door. "Wait, don't go. Can we just talk," I said. She stopped and looked at me. "You just caught me by surprise there, it was a bit much for me to process," I said. She gave me a kind look, and we connected for a second, and I knew my friend loved and cared about me too. But the sexual energy had been ripped out of the night, her pride was wounded, and she felt she had to go. "Bye, Amy." After five minutes, I recalled that Claudia had been dropped off, which was good since she was now definitely too drunk to drive. I looked out my window and didn't see her anywhere in our parking lot. She had called a friend or gotten lucky with a cab. I sat and finished my glass of wine, feeling numb and lonely. I had acted like an inexperienced child, and in the process had treated my best friend like shit. I wanted to call her, but I was too embarrassed, and my confidence was shot. I figured the last thing she wanted to do was hear from me. I knew it wasn't all me, though. If Claudia had been in the right frame of mind and wanted to have sex, she would have seen that I wanted her too and just needed a little more patience with the seduction. She wouldn't have been so easily discouraged. Regardless of where blame resided for her awkward exit, I loved my friend, and I didn't want her to feel bad. So I texted her. I went through several drafts, all too long and over-explaining things. Finally I sent her one simple sentence: "I'm a virgin." Claudia would understand everything. She would know I meant a virgin to men too, not just women. It would explain why her aggressive move with the dildo freaked me out. She would remember our discussions about sex and realize I was vague and evasive not because I was private, but because there were no tales to tell. Yet I never heard back from her. The next Friday came and went with no call, text or email. So this is what it was like to stare at your phone and wait. I was horribly sad. I didn't have a date, so I sat alone in my apartment missing her and wondering why I wasn't calling her. Since the last text was from me, the ball was in her court. If she didn't want to call, I had to respect that. She hadn't been at the gym either, and of course I feared the worst and assumed she was avoiding me. My emotions were all over the place. Despite being embarrassed, lonely, and maybe a bit depressed, I was incredibly horny all the time now thanks to my lover. It wasn't just for her. I thought about sex all the time. It was even becoming a distraction at work. A man would stop by my cubicle to discuss something, and I would imagine him bending me over the desk and plowing me from behind. Something had to give soon or I would go crazy. The next weekend I booked a second date for Friday with my best dating prospect. Charles was a charming, older divorced man with lots of experience. He picked me up in a large, clean pickup with leather seats. The loud, vibrating diesel engine made me horny before we even arrived at our destination. He was tall and handsome and definitely had game, combining just the right amount of mystery and openness. He took to me to a movie, but we stayed in the back row and made out like we were teenagers. For him it was probably just another Friday night date with a chick he met online. For me, it was the first time I had made out with a man for more than about ten seconds. When we got to my apartment, he confidently put a hand on my thigh and said, "I'll walk you up. We could have coffee or something and hang out more." I saw right through that, not that I minded his offer. "I don't have sex until the third date, Charles," I teased him. After making out in a movie theater for an hour, I felt sex jokes were appropriate second date banter. "Better say goodnight here, then walk me to the door." It wasn't the right time of the month for me anyway, but I thought teasing him with a promise of sex on our next date was better than telling him I was on the rag. He laughed. "That's the smartest way a woman has ever ensured she'd get a call from me. I can't wait to have sex with you. Come here." I slid easily across the leather-covered bench seat in the spacious cab of his pickup, then made a quick adjustment to move the seat belt receiver that was violating my backside. We actually had a lot of privacy due to the late hour and the poor lighting on the edge of the parking lot. The risk of someone walking by just excited me more. Charles and I made out again like in the theater, but this time I felt his hand go up my shirt. He cupped my breast outside the bra. "May I?" "You may," I replied. He reached around with the other hand and skillfully unclasped my bra. I felt my heavy tits hang, then his hand was under the bra, kneading the flesh softly. It was heavenly. I was still getting comfortable with my newer, much slimmer body. My confidence hadn't quite caught up with my improving looks, so I was appreciative when he complimented my rack even though it was already one of my best features. I viewed this as an opportunity to experiment also, especially since I had already set boundaries for the night. I reached for his crotch, finding him hard beneath his jeans. I rubbed through his pants, then undid the button to his fly. He helped me push the zipper down. As he continued to massage my breasts, I couldn't really see what I was doing since we were still kissing. I fumbled with his crotch and found the hole in the front of his boxers and managed to pull his erection out. The first thing I noticed was he was wet at the top. I was oddly proud to be stimulating his precome. I clasped the hard shaft, and it just felt small. I could easily reach my fingers all the way around it and form a tight grip. Even though I didn't have much for a standard of comparison since this was the first penis I'd held, I was certain he had a little dick. I was surprised. He was definitely on the tall side, and I just naively assumed he'd be proportionate. This was good news to me. If it wasn't the wrong time of the month, I likely would have reversed my decision and invited him up right then to do the honors. Charles seemed to be interested in me for more than just sex, he had class, and his smallish penis was a little less intimidating for my first time. While I pondered this, I suddenly felt a jolt of pain. Charles had pinched my nipple a little too hard before I was ready. I cringed audibly, and he corrected immediately. His other hand wandered south and found my crotch. He stayed outside the pants for now, but it felt great to have him rub my pussy through the clothes. The pressure against my loins was still intense and like nothing I'd felt from another human. I was already noticeably wet from the make-out session in the theater. I continued to pump his cock, and just when Charles was trying to unbutton my fly, I felt him jerk and suddenly groan into my mouth as we kissed. A hot fluid spread over my tight grip. I had just completed my first hand job. I thought it would be a happy moment and I had done what I was supposed to do, but Charles was embarrassed and immediately got weird. The kisses and breast fondling stopped. I figured he wanted to have sex or get a blow job or something and was upset that he came so fast and without warning. He handed me a napkin for cleanup, which turned out to be kind of gross. I think if he'd climaxed in my mouth, there would have been less mess and I would have liked it more. I had tasted Damon after all on Claudia's finger, so I was confident enough to make an attempt at swallowing. Instead there was a sticky mess on my hand, his clothes, and the seat of his truck. Then there was a dirty napkin to deal with. I left my bra unhooked and told him I could find my own way the short distance to my apartment door since it was a safe neighborhood. I was confused. Charles seemed to be acting like he'd lost his man card, and that it was somehow my fault. But to his credit, he salvaged what could have been an end to our short courtship. He came after me apologizing as I walked to my apartment. His compliments about how my great rack and lovely kisses were responsible for his sudden climax helped his case. He finished the night a gentleman, walking me to my door and wishing me goodnight. It was a wonderful night for me. I gained a lot of experience and thought I handled myself with a lot of confidence despite being so inexperienced. Another week went by with no word from Claudia. Charles didn't call, either playing it cool to drive me crazy, or he just wasn't that into me after the awkward end to our date. It didn't bother me. Perhaps if I hadn't been more concerned about Claudia, I would have obsessed over my "real" dating life, but that just didn't happen. On Friday I got some fantastic news. I'd been working very hard in my first job since college. The company wanted to promote me, but it would mean a move to Baltimore immediately after the new year. I accepted, but I was sad knowing I would be leaving my best friend, especially on bad terms. The next day was our jiu-jitsu gym's holiday party. I'd been looking forward to it for a while. It was sort of an unofficial coming out party for me. Through diet and hard work, I'd finally hit my target weight earlier in the week. It would be the first time a lot of my gym mates would see me with my hair down, and there were two other affiliate schools invited, which meant lots of fit, single men. I wondered briefly if it would be a good night to get it over with and lose my virginity. I sensed my days of purity were coming to an end. Never had my sex drive been higher. I now had a primed, fit body, and I was dying to finally put it to use. I knew it probably wouldn't happen that night, though. These were people I would see again, and while I didn't exactly cherish my virginity, I did want it to mean a little something when I lost it. I shaved my bikini line anyway since I had let it go a bit, just to keep my options open. Giving attention to my pubic area just frustrated me and made me even hornier. I spent a few minutes on the bed rubbing my clit. Thoughts of Claudia filled my mind. I had been so stupid, and now I wasn't going to get another chance. She had been so close, ready to be intimate with me, and I had blown it. Sure, the circumstances of the evening weren't perfect, but she had my half nude body bent over, the dildo at my door and about to slide in. What more did I need? After making out with her and tasting a man's spunk from her vagina, why did a piece of plastic suddenly freak me out? If I had waited another few seconds, there would have been no turning back. What would it have been like? I imagined her joining with me, her tool finally entering me. It was taking me longer to cum than normal, perhaps due to my frustrations. I was already running late. The orgasm would have to wait. Unlike most of the times I put on nice clothes, I really enjoyed getting ready. I started with a new black thong panty that I had bought to celebrate my new body. It was the first thong I'd ever owned. I looked into the mirror for a few minutes, admiring the figure I had worked so hard to improve. I smiled big, able now to ignore quite nicely my remaining imperfections. I took my time working in some body to my red hair. I had never been more confident in my appearance and sexuality in my entire life. I put on a nice outfit that accentuated my large bust and showed a little cleavage. It was tasteful but would definitely attract attention, and on this night, I wanted people to look. Next I squeezed into my new jeans. I'd spent my whole life hating shopping and all things related to fashion, but I had spent over two hours picking these jeans out. I'd carefully selected the pair that made my ass look the best, and fortunately the winner had been under $100. The return of the mom-jeans trend was in full force, but I refused to give in. I had worked too hard on this ass to not show it off. My pants clung to my figure and hung low at the waist. If I sat wrong and didn't hide it, I would definitely show some crack, and I was okay with that. I really enjoyed turning to the side and not seeing any more of that belly pooch sticking out over my pants. I was happy with how my tush looked also. I was confident and ready to impress.