2 comments/ 25139 views/ 5 favorites My First Time With A TV By: marriedandbi This happened many years ago in a small town on the coast in Baja Mexico, I was 20 or 22 at the time. I knew a very hot and very passable TV she was about 5 9' had green eyes and big round boobs, full lips and a soft girly figure. She was always at a bar I went to, we never did anything but did enjoy each others company often dancing. She liked to dirty dance with me making me blush with embarrassment! I was after all a big tough 'straight' guy. She loved dancing and kissing with unknowing American tourists and fishermen. We always talked and drank together to the point tourists {thinking we where a couple} would ask me if I was alright with me to ask her to dance. Well one slow night we along 2 other locals drank until closing time we where all nicely buzzed. She asked for a ride home witch was not uncommon, I said 'sure' as soon as we got a block or 2 away she put her hand on my leg and said 'I could use some fresh air let's lay on the beach for awhile' in a short time we were laying next to each other on a blanket she had one soft smooth leg bent so it was touching mine I began to get aroused but didn't move away so she moved to her side facing me. Up to this point we never fooled around so this was all new for me. I was getting more aroused by the second and adjusted myself she saw this and said 'let me help you' without waiting for a response she reached down and began to lightly massage my rapidly harding cock while kissing my neck when she tired to kiss me I turned my head away she quietly said 'don't worry I won't tell anyone about this' with that my reluctance crumbled {the alcohol helped} she kissed me with those big soft lips and wow she was a great kisser! We continued this for awhile she had removed her top pushing her boobs against me and pulled my shorts down she was slowly stroking and running her long nails up and down my hard dick needless to say I was very turned on so I turned on my side to face her and started to grind against her she responded by doing the same to me, I reached down to grab her ass a slid my hand down her shorts she said 'this might make it easier' and unbuttoned and slid her shorts and panties off. She turned back to me I reached down and felt her large and thick cock it was at least 7in and shaved smooth! I had slid my shorts completely off so now we pressed our naked bodies together while kissing and grinding against each other. Our cocks felt like they where on fire as we held each other tight, she pushed me to my back and kissed her way down to my cock, she gently grabbed and began to stroke me while lightly kissing and licking my rock hard cock and teasing my asshole with her nails,god she was good! She finally took me into her hot mouth and began a long slow blow job, I could feel her boobs rubbing against my legs. She was keeping right on the edge it was unbelievable! I kept thinking is 'she' really a guy? Her soft smooth body made me think about it until I saw her stroke her big dick {bigger than mine} all this quickly {too quickly} pushed me over the edge and I started to fuck her face to a fantastic orgasm shooting cum into her wet hot mouth, she continued to suck until I was soft then came up to give me a long kiss I could still taste my cum on her lips. I reached down to play with her, she moved around so I could lick her while she played with my still soft cock. I tried my best to make come but unfortunately failed, she said 'don't worry' it was because of the hormones she took. She rolled on her back and said 'I need to do it myself' I kissed her as stroked herself to a squirting orgasm. After we softly kissed for a little while longer then cleaned up and I drove her home, it had been a fantastic night so I asked if we could meet the next night? She smiled gave me a kiss and said 'I hope so' She again promised not to tell and saying with a smile 'I'd hate to ruin your 'macho' image' and she never did tell. Unfortunately it was four long months My First Time With A Woman I still remember my first time with a woman. I was nineteen and had been recalled from college by my Aunt Wilhelmina. Father and Mum had run off with the family fortune and I was officially without means. Aunt Wilhelmina gave me options. “Listen, kid,” Willie said, lighting her umpteenth cigarette of the day. Willie is one of those tall, stout women one suspects was born with a white blanket. Willie sported a loose fitting man’s suit and sprawled into one of the large, overstuffed chairs. “You are a beautiful girl. You could get married to any number of men and live an extremely comfortable life. For that matter, you could accept gifts from any number of men and keep yourself quite comfortable while maintaining your freedom.” Willie inhaled deeply on her cigarette. Her eyes narrowed as she studied me. “However, if you decide to date women,” Willie continued, punching out her cigarette and moving to stand behind me, her large, mannish hands cupping my ass gently before alternately squeezing each cheek. I remember leaning my head back against her shoulder and pushing my ass into her hands. “With women, there is no risk of pregnancy. The risk of disease is greatly decreased. And,” she continued, one of her hands bunching my skirt between my legs while her hand found my pussy and began to rub it down, “secretive as we are, you will be more than welcome to have both a private life and a public life without any fear of the two lives meeting.” I turned into Willie arms, and with a move I had perfected during my dating life, I had her single breasted jacket unbuttoned and shucked with my hands gliding inside her shirt. I knew the rules of the game. Women, men, senator or gas jockey. It was the same rule whomever you fucked. Make sure they got theirs and then you would get yours. My Aunt Wilhelmina stands 5’10” and weighed around 200 lbs. She was a tall woman, both broad of shoulder and broad of ass. I, however, was a taller woman, standing 6’3” and weighing about 145 lbs. I am long, lean, with the best, all natural rack. I am sure Willie felt petite for the first time in a number of years. Yeah, she out weighed me, but she got to look up for a kiss. My hands were pleasantly surprised to find two hard grapefruit sized breasts with the absolutely stiffest nipples ever. I slowly pulsed them in my hands while my mouth found hers in a long, passionate kiss. I increased the pressure on her breasts and began rolling her nipples in my palm, making Willie moan deep in her throat. Willie kept trying to lead me to the davenport, but I bullied her body to the glass doors opening into her private garden. Once I had Willie pressed up against the doors, I began to grind my hips into hers. Shocked, I pulled away from Willie to look into her eyes, a huge smile lighting up my face. “Why, Willie,” I exclaimed in mock consternation, “are you holding out on me?” I threw my head back and laughed as I watched the blush redden that old battle axes complexion. In a flash, I had Willie’s pants yanked down to her ankles. There stood Willie, in her open oxford, socks and wingtips, and a huge, black phallus pushing its head out of her briefs with little lipstick kisses all over them. I grabbed the back of Willie’s head and kissed her long and hard. Willie returned my kisses with equal passion, her hand jacking her big, black phallus. “Strip!” Willie ordered, her voice hoarse. Slowly, I stripped off piece by piece, until I stood in nothing more than my heels and stockings. Falling to my hands and knees, I crawled back to Willie, my eyes never leaving hers. Sitting up on my knees, I rested Willie’s ass in my hands before my mouth made love to her thighs. Up and down and back again I kissed and licked each thigh while I massaged her ass. Slowly, I began pushing her legs apart, and inch every couple of minutes. I grabbed Willie’s wrists, held them firm against the window, and began the head bob game. Taking a little bit now, and then a little bit more, I had all 10” of her sliding down my throat, the speed slowly increasing. Before I knew it, Willie had ripped her hands out of their imprisonment. She gripped my shoulders as her hips began to buck wildly against my mouth. When the bucking stopped, I caught Willie’s weight as her knees began to give and brought her down to the floor. With my back to her, I sat down on Willie’s cock, starting my pelvic figure eights. It was exquisite. All that lovely, hard cock pressing against the walls of my cunt. As I continued to pleasure myself, I did not forget about my benefactress. Leaning over, I brought her foot to me and began a firm, sensuous massage, occasionally taking a toe into my mouth, or making love to one of her arches. An hour later, we were both replete, dressed and Aunt Wilhelmina handed me a check for ten thousand dollars. That was my first time with a woman. It was the start of my long and prosperous career as a female’s prostitute. My First Time with a Woman **Here goes my very first real experience submission... I'm nervous! :-) Names have been changed.** I grew up in a small town as a very shy nerdy girl. The topic of sex made my cheeks turn bright red so I would literally run away from my friends trying to discuss it with or around me. My parents never gave me the birds and bees talk so anything I knew about sex came from dad's not-so-hidden porn mags. After graduating high school I knew I had to go to a college far enough away from my family's tight grip on me so that I could relax. I was excited about living in a dorm 3 hours away from my parents and little brothers - I was about to begin a new chapter! But little did I know those first few days what I was really going to learn in the next 4 years. As a freshman in my particular school they started socializing us from the very beginning. We were often taken as a freshman class and told to sit through a presentation or watch a band or we even had a class with a bunch of other freshman where we read and discussed a book. I just do not remember first meeting Dina.... I do remember that we became friends quickly and that we shared some common friends. She was so much fun! Much the opposite of me she was from NYC and was not at all shy! In the first weeks of knowing each other we often watched tv together, went to the cafe at night together, even had sleep overs in my room since my roommate stayed at her boyfriends all of the time. I remember that Dina was very carefree and easy going. We would have deeper conversations sometimes and I remember once that we talked about bisexuality. I had no idea if I was or wasn't, how could I know? I knew the naked women in my dad's mags made me really wet but I never knew what to do about that. Was I bisexual? The convo that night led to sleep and uncertainty for me, although I wasn't bothered by it since I had no dates lined up male OR female. I was just shy, very single me and I was fine with that. So... on with the night in question... Dina knocked on my door one evening as usual and asked if I wanted to take a purity test on the computer. They were very popular and silly and I was always the most pure in the room but I agreed. Not even 5 minutes after she had knocked on my door another knock was heard. I wasn't expecting anyone but Dina jumped up and answered the door. Her friend Roger was standing in the doorway and Dina asked my permission to have him hang out with us. I was fine with that so Dina introduced Roger and I to one another and I sat back down on the beanbag chair. When I looked back up toward my desk I saw that Dina was sitting on Roger's lap on the chair in front of my computer. I was a bit uncomfortable but we started taking the test and it was fine. AGAIN I was the purist person with somewhere in the high 80 percent IF I fudged the answer to a couple of questions. Dina and Roger had much lower scores than me. Then Dina looked at the clock and a tv show she liked was on so we turned on the television. Dina and Roger laid side by side on the bed now with their face facing the television and I was on the bean bag chair right beside them. This time I saw that there was a little touching involved on the bed so I'm sure I was flushed and I know I was feeling uncomfortable. I just wanted to run away! The touching was innocent enough... holding hands and rubbing non-sexual parts of the body....but I still wanted to hide.... what if it went further? Should I just leave? Then they started kissing... luckily it was only for a minute or two! Not long after I started thinking about my exit plan I got my answer... Roger sat up and then got down onto the floor as Dina got on her knees on the bed and looked down at me. She extended her arm toward me and asked me to get on the bed with her so she could kiss me. She reached further for me but at this point I was red and my head was whirling. I was SO scared and uncomfortable that I said no...and that is not the answer Dina wanted. Dina got up and bolted out the door. I slowly got up and sat on the bed as Roger kept trying to convince me to say yes once she came back. My head was still spinning! Roger seemed to be really nice and he seemed very willing to let Dina help me explore my sexuality. (And YES, I was THAT naive...) Maybe 5 minutes went by and Dina walked back into the room and while standing by the door she asked me again if I would join her on the bed... nervously I agreed. I had never noticed Dina's beauty until right now. She was about my height at 5'6" and had curves in all of the right places. Her skin was a deep chocolate and it was so smooth and perfect. She wore her hair in braids, at least that night. Dina got back on her knees in the middle of the bed and asked me to do the same. We faced each other. She told me not to be nervous and then moved her mouth over mine. She slowly taught me the way she liked being kissed so I imitated and WOW... I wasn't nervous for long because her lips and her tongue felt so perfect kissing me. I completely forgot about Roger sitting on the floor and just let her lead the kiss to a 15 minute make out session. We were both breathing heavier at this point and Dina pulled her face away from mine and while hoarsely whispering asked me to take off my shirt and bra. I slowly did what she said while she did the same. As an aside I had seen my friends naked breasts plenty of times before... even taking showers with female friends into my early teens so this wasn't new to me...but this night was different. First of all - Dina has the most perfect size C breasts! Well... they were nice and firm and perky...but we were only 17 and 18 years old so I guess that's normal. Dina asked me to mimic on her what she was about to do to me. She looked into my eyes as she moved one hand to a nipple and started playing with it. No one had ever done that to me before...I couldn't believe how good it felt! I did the same to her nipple... at first we were just rubbing a finger over the nipple area, exploring... and then we were rolling and lightly pinching, bringing the second hand up to play with the opposite breast. I felt like I was in heaven.. Then more suddenly Dina's head bobbed down toward my chest and she started using her tongue on my nipple and I think this is when my eyes closed and my head fell back... and at this point I just remember a lot of kissing and nipple play for at least another half hour. When the position on our knees got too uncomfortable Dina sat down on the bed and asked me to lay on the floor with my feet toward the bed and I did what I was told. Roger was still just laying on the floor near the couch but I wasn't paying much attention to him at all. Dina caught her breath for a minute and just looked at both of us. She came down to the ground and straddled Roger, bringing her mouth to his and making out with him for a few minutes. I heard a zipper while Dina moved herself to the side of Roger away from me and then I watched as she slowly freed Roger's very erect cock from his tight jeans. Dina moved her apparent expert right hand up and down the length of Roger's cock while I just stared. I then noticed Roger was now in his own little world with Dina and I was no longer in the room. Dina moved again back over Roger in between he and I, never moving her hand away from his hard member. She then started playing with my nipples which apparently woke Roger back up as he stared at us....I strangely no longer felt uncomfortable. Dina kept up her massage of my breasts then moving her left hand to my pussy and rubbed me from over my clothing. At this point I hadn't learned how to masturbate yet so I really didn't know what she was doing. (Again - YES, that naive!) I knew it felt good and that's what mattered. After a few minutes of this Dina took her hand from me and then moved herself right in between Roger's legs indian style. She then started to pick up her pace on Roger and it didn't take long for him to arch his back, let out a little grunt and then spit cum into the air, hitting Dina's breasts and stomach. I think that's when we all felt a bit awkward after a minute of just sitting around so everyone got redressed and Dina and Roger decided to leave while I was left with a head full of new questions and desires. Dina and I never even kissed again after this incident. I do realize now it was a complete set up but I'm happy it happened! I now have a hot story with a hot girl to remember forever....