14 comments/ 207710 views/ 74 favorites Her New Girlfriend Ch. 01 By: grgy56 Chapter 01: Discovery Like most guys I guess, I like women's sexy lingerie except I like to wear it too. I love putting on my girlfriend's undies, walking around the apartment in them and masturbating until I explode all over the place. Cheryl my girlfriend is on the athletic side and her things easily fit on my more slighter frame. She is very shapely with long sculptured legs, a tight body and C-size breasts. Her dark thick short hair just reaches her shoulders and frames her attractive face: Big eyes; big pouting lips and almond eyes. She really is a total package. She always dresses hot with tight outfits, short skirts and high heels. Underneath, she almost always wears lacy bras and panties. I love making out with her when she is dressed up and I can feel her sexy undergarments rub against my skin. Cheryl was gone for the afternoon so I took my time and went through her lingerie drawer. I tried a couple of different things and paraded around but decided on her red lace bra and matching panties. They must have been new since I had never seen them before. The panties would have been just large enough to cover her pussy so it was difficult for me to contain my cock inside them. I had to kind of tuck it under to try and contain it. I walked around our bedroom and admired myself in the mirror. I thought I looked pretty good. My body is pretty hairless, so from the neck down, I looked very feminine. The outfit on my slim body was perfect and my legs were shapely for a female never mind that I was a male. I found some matching stay up stockings which really made me look totally hot. As I pranced around the room in front of the mirror, my cock popped out the top of my panties. It reminded me of some of the TSTV web sights I visited and I stroked and rubbed my cock and balls through the lacy material. Finally I couldn't stand it any more. I jumped on the bed and vigourously started to jerk off. I grabbed her vibrator from the night stand, lubed it then rolled over onto all fours. I pulled my panties down just exposing my ass and turning the toy on to low. As I place the tip right on my back door entrance, it ran a shiver right through my body. I pushed it inside me a bit at a time until most of it was inserted. I turned it up more and more. Then I let the pressure from my sphincter push it out before I pushed it back in like it was fucking me. I turned it to max. My entire body was shaking. With the vibrator fucking my ass, I barely had to touch myself when I started to climax. I shot my huge load all over the bed underneath me. The vibrator shot out of my asshole as I collapsed face down on the bed. My cock smeared into my warm pool of cum beneath as I continues to experience mini-spasms from my orgasm. Finally gaining enough strength to move, I got up. "Shit!" I realized I just smeared my....her panties and stockings with cum. I threw the panties in the hamper and prayed she wouldn't figure anything out. I had to hand wash the stocking because I knew you don't machine wash them. I hoped they would dry before she returned. I didn't realize how late it was. I put back her bra and stockings then cleaned up the bed and replaced the toy just in time. "Hi honey!" Cheryl shouted. "I'm home!" "Hi!" I said still excited but trying not to look guilty. "How was shopping?" "Bought some new girlie things. Maybe we can have a fashion show later." Cheryl winked at me as she went to the bedroom to put her stuff away. We had some dinner, but my mind was elsewhere thinking about the new outfits Cheryl bought and how they might look on me. "Let's watch some TV." Cheryl said out of the blue. "I've got a new DVD to watch, but I'm going to change into something more comfortable." which usually meant she was going to put on some of her sexy things and we'd watch some porn. She took a little time to get ready, so I cleaned up the dishes. I was disappointed when she came back wearing her dressing gown since I wanted to her to show me her new outfits. Then she let the front of her gown fall open. "Holy shit!" I thought to myself. "Is that the same panty I jerked off in?" I thought I could see some cum stains. She slid in the DVD into the player and cuddled beside me on the couch. "This should be interesting." She said as if it were a documentary. I looked puzzled as it started to play. It looked familiar. It was in our bedroom. It was me! "What is this?" I asked. "I kept finding my panty drawer disturbed and who could be going through my things, so I set up the DVD recorder in our bedroom. And voila! My hard core proof it's you." "I know some guys like to use women's underwear to jerk off.....But oooh! Look at that! I didn't realize you like to wear it too!" Cheryl said as she saw me in one of her white thongs. "You look good in that one." I was stunned but tried got up to turn it off. Cheryl threatened me. "Don't you dare. I want to see this." I stood there like a stupid dolt with a huge tent in my sweat pants. She watched me try on a number of different bras and panties; a couple of teddies and her bustier. Finally I put the red lacy bra and panties. "Oh yeah!" Cheryl exclaimed. "Those suit you best. They look better on you than me, don't you think?" As she showed me her panties; the ones I wore earlier and still smelled of cum. Then she watched me start to masturbate. "You look really hot jerking off like that." She observed. Then the vibrator part viewed. "Oooh, my little girl likes it in her ass!" Did she just call me her little girl? Then finally, I came and collapsed. My cock was so hard right now, it almost burst out of my pants. "Well, my little girl likes frilly lacy things. Let's try on some of the new things I bought today." She told me to wait where I was. My body was tingling with excitement as Cheryl ordered me to change in the middle of our living room. Standing there naked while she decided on what I should wear, had me rock solid. She made me try on a number of things she bought, and then handed me a hot pink thong with a butterfly over my crotch, however my rock hardness could not be contained and was sticking out the top. "You need to fix that." She pointed at my hardness. "How?" I asked. "I'm too excited for it to go down." Cheryl licked her lips and smiled. "Think about it." I stood in the middle of the room with this massive hard on sticking out of my panties. I tentatively moved my hand to my crotch and took hold of my cock. Cheryl looked at me with lust in her eyes then whimpered as I started moving my hand up and down. I was so horny, it felt like only seconds as I jerked off and shot a wad on the floor in front of me. I could barely stand after coming, but that did it. My cock was soft enough to tuck inside my panties. Cheryl then had me put on a pair of black fishnet stay ups but made me put on a beautiful red and black bustier with garters to hold them up anyways. Cheryl also loved wigs. She had many in her wardrobe and would put them on when she wanted to go out to be slutty with me and not be recognized. Cheryl put the red one on me. As I stood in front of a full length hallway mirror, Cheryl approached me from behind. One of her hands cupped my bum then down my crack and between my legs. Her other hand tweaked my nipples. I stood there unable to move. My legs were still trembling making it difficult to stand. Her hand ran down my chest, over my belly and on to my crotch. She played with my balls through the thin panty material. Her other hand reached around and started stroking my cock. She pulled my body into hers and ground her crotch into my ass. Cheryl grabbed me by the scruff of my neck, led me to our bedroom and threw me face down on the bed. Out of the corner of my eye, I watched her grab the lube bottle and pour it over my ass. She then grabbed her double-ended cock-shaped dildo and lubed it against my ass. Holding it from the middle, she easily inserted one end into her wet cunt then aim the other end on my lubed soaked asshole. She pushed with constant pressure as the cock head popped inside me. Her left hand pushed my head into the bed as she thrusted her hips back and forth causing the dildo to fuck both of us. I could no longer hold back. I started to shoot my cum between the bed and my body while Cheryl continued humping me until she was able to orgasm as well. My body was totally spent; every muscle was twitching; my cock still spasming from the massive orgasm I just experienced. I couldn't move even if I wanted to. I laid on the bed with the dildo still sticking out of my ass when I heard "Click! Click!" I turned to see Cheryl taking pictures. "This will be easier for me to carry around and show rather than carrying the DVD." At this point, I really did give a damn what she meant. "I'll have to think about what to do about our little secret." That night, Cheryl made me sleep in one of her short black embroidered baby doll with panties. Even though I was exhausted, between my new sleeping apparel and what she might have planned for me, I didn't sleep a wink that night. Her New Girlfriend Ch. 02 Chapter 2: Transition I stayed awake all night thinking of what transpired the day before. My girlfriend Cheryl secretly recorded a DVD and caught me dressing in her lingerie and masturbating with her vibrator deep up my ass. After the grand viewing, she dressed me up in some of her lingerie again, put one of her wigs on me and fucked my ass with her double headed rubber dildo until we both came. This morning, my hard on strained against the flimsy material of her panties she made me wear to bed last night. Cheryl finally stirred awake. "Hello girlfriend." She said as she reached under the baby doll she also made me wear. Her fingers found my already hard nipple and tweeked the agressively. My cock jumped. Cheryl slid her hand down my tummy and between my legs to find me hard as rock. "Well that will never do." She said. Cheryl threw her vibrator at me. I looked at the vibrator then at Cheryl. She returned an affirmative stare at me. I knew what I had to do. I pulled my panties down to my knees and rolled up onto my knees. I switched on the vibrator and placed the tip against my bunghole. The vibrations immediately sent shivers through my body. I started to jerk off. "Good girl!" I heard Cheryl say. "That's so hot!" It wasn't take long before I started spurting my cum on the sheets beneath me. I remained on my knees; my face buried in my pillow; my body convulsing ever so slightly with the vibrator still sticking out of my ass. Finally, I rolled onto my back. My prick was still as hard as ever. "Hmmph!" Cheryl expressed. "Again!" "But ..... I can't!" I cried. "It's too sensitive." "Do it or I'll do it for you." Cheryl ordered. I tentatively wrapped my hand around my stiff and slowly moved my hand up and down. The sensitivity of my cock ran through my entire body. "Put your ass on top of the wet spot, just like you make me after you come." I moved my ass on top of it; my hot cum had since grown into a cold pool. Cheryl knelt between my legs and put them on her shoulders. My panties were still strung across my knees. Cheryl took the vibrator and fucked my ass as I jerked off. As she shoved it deep inside me, I shot my second load onto my chest and belly. My body was involuntary jerking in response to the overload of sensations. My dick finally started to get limp in my hand. "Have a shower and clean yourself up. We have a lot to do today." Cheryl then added, "Unless I approve, you will not be allowed to have an erection in my presence. Do you understand?" I nodded my head up and down. I had to wait until Cheryl was finished with the bathroom before I was able to shower. Not wanting to get into trouble again, I laid in bed, my ass soaked in my own cum and my last load crusted on my belly. I emerged from my shower to find Cheryl dressed and ready to leave. She held out a short trench coat. "Put this on and let's go!" "...but I'm naked!" I started to protest. "I don't want you wearing my things and since you don't have any proper clothes of your own..." I put on the coat. It was so short, the hem only came down to my mid thigh. At least she let me wear my own shoes. We got into her Miata convertible and I found it difficult to keep covered with the short coat on. Fortunately it was a short drive to our destination. But it wasn't a cloth store. It was a spa! I got out of the low car as carefully as I could but was unable keep anything hidden and ended up flashing my nakedness to some females passing by. They pointed and giggled at me as they scurried away. I guess I looked confused as I followed Cheryl into the store. "Well we can't have my new girlfriend looking like that when we go shopping." She told me. Jacklyn, Cheryl's friend and owner of the spa greeted us. "So who's your new girlfriend Cheryl?" Jacklyn asked. "This is.." Cheryl paused to think. "Gina. She's here for the works." "Well let's see what we have to do. Take your coat off Gina." I looked around. Even though it was still early, there were a couple of women clients around as well as some of the female staff. "Gina!" Cheryl looked at me sternly. I slowly undid my coat. One of the staff took my coat from me and gasped to find me naked underneath. The other spectators pointed and giggled. Fortunately I was too embarrassed to get hard. "The works!" Cheryl and Jacklyn agreed in unison. I was lead into a room where I was scrubbed down. Every hair on my body was then removed. Fortunately, for a male I had very fine blond body hair, but getting my waxed was still extremely painful. Both Cheryl and Jacklyn watched and were amused as the sexy female technician manipulated my cock and ball to remove any stray hairs and inspected her work as I tried hard not to get hard. I was told to go into "Down Dog" position to get my ass done. That really hurt. Then the cute technician applied some lotion to ease the pain paying special attention to my asshole. I felt her finger massage my backside entrance before she started to push it inside. She pumped it in and while stroking my prostrate. Even with that I was able to maintain a limp cock thanks to masturbating earlier. I later found out that Cheryl signaled her to do finger fuck me and try to get me hard just so I would have to jerk off in front of them. Then I was given a wonderful facial and body wrap, manicure and pedicure, nail extensions paint a bright red and heavy make up to hide any remaining masculine traits. Finally they affixed a strawberry coloured wig to my head. It was shoulder length with full, soft curls. "Gina, get your coat." Cheryl ordered. "We've got another stop to make." She turned to Jacklyn and said "Great job Jacks. See you tonight!" I put on my short coat and looked at myself in the mirror. I thought I looked pretty hot. Then I thought "Huh? Tonight!?" As we drove in the Miata, I didn't even bother trying to cover myself up. In fact, at one red light, a trucker pulled up beside the car. My coat had fallen open and showed my crotch. I had tucked myself between my legs and from a distance it looked like a shave pussy. The trucker gave me a long wolf whistle as we drove away. "Oh you do like being slutty." Cheryl noted. I smiled back proudly. We arrived at our next destination without further episodes. I got out of the car and flashed some older gentleman walking by. He looked at me and smiled. We walked into the store; a kind of "Frederick's of Hollywood." Immediately a clerk came up to aid us. "I am Pierre. May I help you?" There was definitely something feminine to his voice. "Yes, we need a couple of things for her." Cheryl replied and referred to me. Pierre looked at me and smiled recognizing I was in drag. Cheryl and Pierre had me try on a number of different lingerie and things including bustiers, garters with stockings, and panties and bras. Pierre was very helpful assisting me with the outfits. "Something is missing Pierre. I think she needs some help upstairs." Cheryl said referring to my lack of boobs. "Can you help her grow to a size C?" Pierre left and came back with some skin toned silicon falsies. They fit perfectly and kind of sucked on to my chest like they were actually mine. With skin tone colouring, you couldn't tell they weren't real. The last piece I tried on was a pretty lacy pink bra and matching crotchless panties. They were open in the back end for you know; and the front had two ties keeping the front closed. Pierre knelt in front of me, held the panties open as I stepped into them, then he pulled them over my hips. As he reached around to make sure they were in the correct fit, his face "accidentally" rubbed against my noticeable hard on. "These panties have these cute bows which untie for access." Pierre said stating the obvious. "See?" Pierre tugged on the lace bow. My hard cock popped out and hit Pierre in the face. "Oh my!" Pierre said excitedly. Still holding my hips, he opened his mouth and took me in. With a practiced mouth he sucked my cock until I exploded inside his mouth; then placed my cock back inside and ties my panties closed. I looked over at Cheryl who had played with herself and also just cum from watch Pierre and me. "That's perfect Pierre. We'll take that and these things too." Cheryl told him. "But that coat won't do. We need something she can where outside." The both of them opted for a tight white blouse opened to expose my new deep cleavage. The buttons strained to keep my "tits" contained inside. Next was a short demin skirt with white knee-high stockings and black strappy 4-inch heels. I was use to wearing Cheryl's heels so this wasn't a problem. "Pierre, please personally deliver these things to my place at 8.30 tonight." Cheryl said. "We're having a Gina fashion show and she'll also need you to help her with her outfits." "Of course. I should not have any problems." Pierre answered. We left the store and stopped at an outdoor café. I sat facing Cheryl and the street. The short skirt rode up my thighs and back side as I sat on the patio chair. I tried to keep my legs together, but the short skirt made sure it difficult to keep things lady like. As we have some coffee, Cheryl made a number of phone calls. Meantime, the surrounding tables were all occupied by men trying to eye inside my blouse and under my skirt. Inside my panties, I could feel my hard cock leak precum. I dared not let Cheryl know in case she made me "fix" myself there in the open. "Come on Gina." Cheryl ordered. "Time for home and get ready for tonight." "Tonight!?" I said to myself. "What's tonight?" I was to find out soon enough. Her New Girlfriend Ch. 03 Chapter 3: Completed Well up to now Cheryl videotaped me in her underthings and masturbating; she took me to her friend's spa where I was made hairless and made up to look more feminine; then purchased a number of sexy outfits and put on public display. Quite a full day by any other standard, but we weren't finished yet. "Ding-dong!" the front door. "Gina! Answer the door!" Cheryl called out. I opened the door to find a deliveryman with a big box. Cheryl came up behind me. "Great! It's here." Cheryl exclaimed. "Gina, take the box inside." Cheryl dismissed the delivery guy and entered our living room. "It's for you Gina. I want you to change into that now. Rinse out and save what you have on now for later. " I was still wearing my tight blouse and short skirt over my new favourite bra and panty set. I got undresses and rinsed out the pre-cum and cum that coated the inside of my panties then set them to dry. I unwrapped the new outfit. It was a short frilly yellow house dress. There was also a white demi cup bra and French cut panties; garters and sheer stockings and finally a pair of white high heeled pumps. I quickly donned my new apparel. The front button dress opened low enough to show some cleavage on top and high enough to show my legs as I walked. "Ding-dong!" "Gina! Door!" I dashed to the door anxious to see who it might be. Another deliveryman dropping off food. He was a heavy, scruffy Italian chewing on a toothpick. He gazed upon me with hungry eyes. I took one box of food and told him to follow me into the kitchen with the other. We put the boxes on the counter but I accidentally knocked over some napkins. As I bent over to pick them up, I felt the back of my dress rise up and almost exposed my bum for the delivery guy to see. He immediately placed his hand under my dress and on my ass. Surprised, I just stayed still, bent over, ass in the air. Delivery guy started rubbing his hand over my ass; sliding a fat finger between my cheeks. His hand came awful close to my hidden package. I heard a zipper and a grunt. I looked around and saw him slip his hard 4-inch stubby under my dress. I felt him rub it up and in between my crack. Slowly he lifted the hem of my dress over my hips and was about to lower my panties when we heard Cheryl. "Normally I would let you fuck Gina's ass, but I need to keep her pristine down there," The delivery guy looked pissed. Cheryl continued "but I'm sure she'll be willing to suck you off if you're that desperate." I quickly looked in shock and fear at Cheryl. Dressing up as a female was one thing, but I had never even thought of this before. Okay, Pierre did suck me off at the lingerie store but that was different wasn't it. Cheryl gave me that stern look of warning if I didn't do it. So I dropped to my knees. Tentatively I opened my mouth to take in his slightly pungent cock, but Delivery guy grabbed the back of my head and shoved himself into my face. It wasn't long but it was fat and more than a mouthful. He continued to hold my head and fuck my face. I started to relax a bit and even started to enjoy it when Delivery guy started to grunt and spurt his cum down my throat. He only shot about 6 short squirts but it caught me off guard and I started to choke and gag on it. Most of it spewed over his deflating tool and onto my new dress. Delivery guy quickly zipped up and scurried away. I was left kneeling in the middle of the kitchen floor with my lips all glossy from my saliva and Delivery guy's cum. "Put the things away and then clean yourself up." Cheryl walked away. "I've saved your ass.... For now." I just finished cleaning up and refreshing my make up when... "Ding-dong!" I tried to dash to the door before... "Gina! Door!" I opened the door to find Jacklyn and a few of Cheryl's other friends waiting. "Gina! Let them in." I didn't hear Cheryl come up from behind. "Girls, I'd like to introduce you all to my new girlfriend Gina." Cheryl said. "My fairy boyfriend doesn't live here anymore and Gina has moved in." Everyone smiled and welcomed me with a hug. Jacklyn whispered in my ear. "What a transformation! We did an incredible job didn't we?" I smile and nodded back. After everyone settled, I got them drinks and laid out the food we got earlier "Ding-" I was already heading to the door. "Dong!" It was Pierre with my beautiful new outfits. "Girls! This is Pierre." Cheryl made the introduction. "Gina is going to give us a little fashion show and Pierre is going to help her get ready." All the girls smiled and oohed. I sort of stood there not knowing what to do, but Pierre grabbed my hand and led me to the bedroom. He saw my favourite pink outfit laid out on the bed and smiled. "Cheryl wants that one last." I told him. "Okay." Pierre answered with a bit of a lilt. "This one first then. Get those things off hon." Pierre waved his finger at my current attire. "Put this on first. It should help control your willie." Pierre handed me a thin g-string looking thing. The small patch of lace was strong enough to control "willie" but ultra-thin and holey enough to let me enjoy the sensations of my wardrobe. First was a white silk cami with lacy trim. It was loose and covered my tummy and ended just above my hips. Then Pierre helped me put on the matching silk white boy panties which felt like cream. White slip ons to match. I went out to show the girls. I was met with a few giggle and a lot of oohs. As I passed in front of each of them, they all caressed my ass. Cheryl reached in between my legs and checked to see if I was hard. Luckily I was too nervous to have an erection. After a few different outfits, I started to enjoy showing off for Cheryl's friends. I rushed back to the room and Pierre had my next outfit ready. In a hurry, I pulled everything off including the small thong containing "willie." Pierre handed me a black lace bustier with suspenders attached, matching panties and stockings with of course high heels. I quickly put them on then realized I didn't have my little "willie" thong. Too late as Cheryl call me out. I walked nervously into the room. Everyone cheered as I paraded around. Each girl ran their hand along my body and grabbed my package. I couldn't help but get hard. I tried to hide it long enough to escape but Cheryl saw it. "Gina, you know what you're supposed to do." I looked at Cheryl for sympathy which wasn't coming. How was I suppose to do this in front of all these women. "Gina!" I slowly reach around my waist and pushed down my panties to my knees. My cock was rock hard and jutting upwards. I looked at my audience. They all looked at me in hunger. "Now Gina" Cheryl was growing impatient. I wrapped my hand around my shaft and slowly started to jerk off. I tried to come as quickly as I could but to no avail. The harder I tried the less it seem to work. "Poor Gina seems to be having some problems." Said Jacklyn. "I think she needs some help." With that she knelt in front of me and started to suck my cock. She was good. I wasn't allowed to come in her mouth, but I did manage to cum. I spurted all my cum on the living room floor in front of a half dozen women. At the end, they all cheered as I was only able to stand there quivering from my climax. Cheryl made me clean up my mess then go change into my final outfit. I was shaking as Pierre helped me into my lingerie. The panties were the pretty pink crotchless ones tied closed with two bows. The matching bra held my falsies in place. Knee high stocking. Black high heels. My short demin skirt and white blouse. I wobbled into the living room as all the girls cheered. "Pierre! Come out and take a bow." Cheryl called out. "Everyone. This is Pierre who helped our Gina get ready this evening. Please give him a round of applause." Everyone including me cheered. "Well Gina. I don't think that you gave enough appreciation to Pierre." Accused Cheryl. "Bend over!" Again I looked at Cheryl, but not understanding what was about to happen. "Spread your legs and bend over." I slowly parted my legs and bent over. Pierre moved behind me and lifted my skirt over my hips. I turned to look at Pierre as he unzipped his pants and took out his cock. I looked in fear at the size of this monster. It had to be 8 inches long and thick. It never occurred to me that he would have such a beautiful, huge willie. I started getting hard again, but my panties contained me. I waited in anticipation. Cheryl handed Pierre some lube. He poured it into the crack of my ass and allowed it to drip down. I felt his finger massage the oil into my anus. He pushed a finger deep into me. I felt him play with my prostate. I needed him in me. "Fuck me Pierre!" I begged. Pierre lined his big cock with the entrance to my hole. I felt him pour on more lube before he started pushing it into me. It felt so huge as he continued to shove his entire cock into my bowels. My mind was in overload. In the background, I could hear the girls cheering and urging Pierre. "Fuck him harder!" "Faster!" "Stick you dick into him deeper." And he did. He pounded my ass for what felt like an hour; harder and faster until I was about to cum, but suddenly he stopped. He slowly pulled himself out. I felt so empty. I looked at him begging for him to spear me with his weapon. Pierre gently laid me onto the floor and moved between my legs before putting them on his shoulders. My cock was solid again, Cheryl gave me a stern leer. So as Pierre inserted his cock into my ass again, I started masturbating matching his in stroke with my down stroke. Then Pierre lifted my hips straight up so my ass was in the air. He continued ramming me as I jerked off. I squeeze my anus as tight as I could and I could feel he was about to come. His breathing was increasingly heavy, almost panting. I too was ready to come but concentrated on coming at the same time as my man. Finally he grunted. His balls tightened as his thrusts became shorter and faster. He began shooting his load into my ass. I started to come at the same time. What I didn't realize that when Pierre lifted my ass, my cock was aimed right at my face. "Oh yes Pierre!" I screamed. "Fuck me! Give me your cum!" I started spewing a huge load onto my face. I felt like a hundred guys bukaked me. Pierre pulled himself out and let my ass drop to the floor. The girls were cheering and applauding my ....our show (after all I couldn't have done it without Pierre). Cheryl was grinning and clapping. "Well girls, from the sounds of it, you all enjoyed Gina's completion to femininity." She turned to me. "Gina, clean yourself up." Without blinking, I started licking my face. Anything I couldn't lick, I scraped with my finger and shoved into my mouth. Pierre told me to get on all fours. I was kind of scared since my asshole started to hurt a bit from the hard fuck he just gave me. I tentatively turned over and stuck my ass in the air for him, but instead of feeling the knob of his dick, I felt his tongue. He cleaned me out completely until I came again. I laid on the floor exhausted. Pierre, lifted me up and carried me to the bedroom where he put me to bed and I promptly fell asleep. Her New Girlfriend Ch. 04 4 - Overtime So let me recap the events leading up to now. My girlfriend Cheryl video-ed me in her lingerie and masturbating. She fucked my ass until we both came. She first transformed me into a very attractive female by giving me the full spa treatment including a total body hair removal, facial, manicure, pedicure, wig and makeup. Cheryl also gave me a more fitting name, Gina. Then she took me to a sexy lingerie store where I was outfitted in various sexy bras, bustiers, garters, stockings and panties. We were more than ably assisted by the feminine Pierre who gave me my first male blowjob. While we prepared for a fashion show featuring me for Cheryl's other girlfriends, I gave my first blowjob to some rough delivery guy. That evening, I dressed in my outfits for the girls. The night was ended with me given my first anal fuck from a male, well sort of, it was Pierre. Who would have thought he possessed such a big, beautiful cock. Well that was a lot of firsts for me in such a short time. My head was spinning with excitement. The rest of that weekend, Cheryl made me stay in drag which pleased me to no end. I think it turned her on too. She must have fucked my ass with her strap-on at least a dozen times. I had a lot of difficulty sitting down after that. Monday, I got up for work. Showered, shit and shaved. I went to get dressed only to find all my male underwear gone. "Hi girlfriend." Cheryl often called me that rather than the name she gave me for some reason, but I really liked it when called me her "girlfriend." "Where's my stuff?" I asked. "You will only wear your new undies when ever you go out." She replied. "But I'll let you wear your normal clothes on top." I giggled with excitement. "Okay." I replied in kind of a girly voice. Cheryl helped me select my undergarments: sheer black panties, black garters with a small, red bow in the front and black stockings. On top, I slipped on a matching sheer black cami. I looked in the mirror and could not believe how hot I looked or how hard I was. Cheryl just stared at me angrily. I looked back at her apologetically and started jerking off abiding by her rule of no erections in her presents. I stood in the middle of our bedroom then pushed my panties down to my knee. I firmly gripped myself and started moving my hand in the traditional manner, but it felt totally different... erotic, sexy, hot. I'm not sure how to describe it. It was euphoric. Cheryl stood there and watched. I could see that hunger in her eyes which only made me want to please her more. I was close to cuming when she said. "Don't cum on the floor! I'm tired of seeing your stains all over the place." I felt the surge coming. There was no stopping it. I had no other option I could think of but to cum in my free hand. "Aa.g.g.h!" I groaned as my sperm shot into my palm. I came so hard my knees were about to buckle. I looked at my handful of cum and it was about to spill over. I couldn't run to wash my hand since my panties were still around my knees and I didn't want to soil them by pulling them up. I looked at Cheryl. She only stood there and looked back at me. "What am I going to do?" I started to cry to myself. I slowly brought my hand of cum to my mouth and looked at Cheryl again. She nodded. I tentatively started to lick my own sperm. The taste was like nectar so I lapped my hand clean trying to drink every drop. Satisfied, Cheryl let me finish dressing and off to work I went. Work was great. The sexy undergarments felt great rubbing against my skin. It made things hard, especially in my panties. I was almost disappointed that Cheryl wasn't there to see my erection and make me jerk off again. Over the next couple of weeks, my wardrobe of under things grew. So did my outerwear; short skirts, tight tops and high heel CFM's. Cheryl even took me out on a girl's night with some of the others who were here for my fashion show. The first time out, some guy tried to pick me up at the bar. He placed his hand on the small of my back and let it slide down until it was caressing my ass. I probably would have sucked him off, but Cheryl and the other girls saved me. I got more daring each day at work. I wore a very light underwired satin half slip under a very opaque women's blouse hidden under my suit jacket and tie. Under my pant I wore the matching white satin boy shorts with garters and white stockings. Of course I looked incredibly hot. Of course I got hard. And of course Cheryl was there to watch me jerk off and drink my own cum. All of which I really enjoyed. I finally made it to the office. It was warm but I kept my jacket on all day regardless. But near the end of the day, my manager Katherine asked me to help her get some boxes from the storage room. Katherine is a tall 5' 10" beauty with long, straight, thick, dark nugget brown hair and intense green eyes. She has fair, smooth skin, large C breasts on top of a well toned, shapely body and long legs. Many of the other girls called her a "dyke" because she was often aloof with many of them and had an aura of superiority about her. As a manager, she always was impeccably dressed. Today she was wearing white slip under the jacket of a red business suit. The skirt was knee length and had a slit half way up her right thigh. Her makeup was subtle and perfect. We went to the back and she showed me which boxes she wanted down. I started to reach for the first box when Katherine said "Better take off your jacket or it will get dirty." Without thinking, I removed my jacket. Katherine stared at me. Well not me but my attire. I was so comfortable I forgot what I was wearing underneath. Katherine didn't say anything. I got the boxes, put my jacket back on and moved the boxes to where she wanted them. "Please come to my office." Katherine asked softly but firmly. I followed her to her office not knowing what was going to happen. I took a seat as she shut the door and sat behind her desk. "First, I have no problems with your private life or your office attire." She stated. "We all have secrets and I want to let you know, what I saw is no one else's business." "Thank you Katherine." I gave a big sigh of relief. "That's really understanding of you." She continued. "Does Cheryl know?" I had forgotten they had met at company functions. "Yes. She approves actually." I informed her further. "In fact, she helps me pick out my wardrobe." Maybe that was too much information. "May I see more?" Katherine asked. "Take off your jacket." It was more of an order than a request. Her voice was so commanding I had to obey. I stood up and removed my jacket then placed it on the chair behind me. I began to shake nervously. "Very pretty." Katherine complimented. "Anything else?" I could only nod. "Show me." I removed my shoes and socks first. Katherine immediately noticed my stocking feet. "M.m.m.m." She moaned. I unbuckled my belt then loosened my pants and let them drop around my ankles. I stood in front of Katherine in my satin undergarments! My stiff cock made a huge tent form in the light material of my boy panties. "What is your name?" Katherine asked. "Huh?" I looked at her in a quizzical manner. "You know my name." "No, your name." Then it donned on me. "Gina." I said sheepishly. "Well Gina. I 'm pretty sure Cheryl wouldn't allow that." Katherine was referring to my boner. "What does she make you do to fix it?" I was kind of stunned. My boss was essentially telling me to masturbate in front of her. "Perhaps you need a little incentive." Katherine offered. She stood up and removed her jacket and pulled her slip over her head. She was wearing a red demi bra that cradled her massive orbs. Her red nipples were pointing directly at me. Katherine took licked her fingers and pinched each one of her cherries, but I stood the unmoving. My cock was jumping inside of my panties. "Not enough?" She asked. She reached behind and unzipped her skirt letting it drop to the floor. Her slip followed. She wore tiny, tight, red lacy panties with stockings held up by a satin garter. She pulled her panties down and exposed an 8-inch uncut penis. "Inside I'm a woman but I didn't have the courage to cut it off." Katherine explained. "I laugh at the upper execs when they say I don't have the balls to go any higher in the company." Katherine's tool made mine look like a toy by comparison. I stared in amazement as I pushed my panties down around my knee like I've done for Cheryl so many times before. I started to fist myself while still staring at Katherine. I knew I'd come pretty quickly. Katherine stepped out of the pile of clothes about her ankles and walked around her desk to in front of me. She stopped my hand from jerking off and replaced it with hers. Her hand felt so soft as she started sliding it along my shaft. For my part, I stood there motionless. Katherine then fell to her knees. Her hands reached around and grabbed handfuls of my ass cheeks. Her mouth closed around my dick as she pulled me into her face. Her nose pressed into my body as I was totally inside her mouth. It was unlike anything I felt before; completely different from the blowjobs I received from Cheryl or Pierre. Her head was almost motionless as her throat seemed to be sucking me. "A..a..a.....h!" I moaned as I started firing my load directly into her belly. Even after I was empty, she continued to suck me, ensuring every last drop of semen was drained from me. "Good girl Gina!" Katherine praised as she licked her lips. "See? Now you'll be able to please Cheryl by not wrecking your beautiful clothes she picked out for you." I was totally spent. I couldn't get a stiff even if my life depended on it. "But now I have the same problem." Katherine said as she stood up and referred to her tent pole. I was about to drop to my knees and return the favour, but Katherine quickly grabbed me and pushed me face first over a chair and held me there. "But...What are you...?" I knew what was coming next. I wanted it. I needed it. But what if Cheryl found out. Was I was turning into some sort of office slut? Katherine spit into my ass. I felt the knob of her cock rub it into my winking hole. She placed it onto the opening and paused. "Gina, you can be whatever Cheryl wants at home, but at work you're mine." Katherine increased the force pushing her fat knob into my tight ring. I was use to being "fucked" by Cheryl, so Katherine's cock slid into me easily. "Oh! Yes! Fuck!" I grunted. "Gina likes that doesn't she?" Katherine was pleased. "Hmmm. Mine hasn't been the first in your tight ass has it?" I shook my head "no" And groaned as she drove all of her inside me. Her rhythm increased, smashing her hips into my ass. I sensed it was only a couple of seconds until.... "I'm c..u..m..m..ing!" Katherine screamed as she shot her load deep into my bowls. I felt spurt after spurt of her seed ejaculate in my ass. I did not realize that I to had ejaculated again. Kathleen pulled out of me leaving me bent over the chair with my ass in the air. Cum was leaking out of my asshole and dripping from my own dick. Katherine then grabbed my panties and pulled the over up over my hips; then smeared all the cum the inside. "What am I going to tell Cheryl?" I fretted. "I expect you to be mine as I wish at the office if you don't want to be humiliated." Katherine warned me. "And don't even think of quitting." I silently nodded in agreement. I loved getting corn holed by Katherine, but what to do about Cheryl? I got dressed and took the transit home; cum was still leaking out of my ass. I could smell it permeate the air in crowded bus. I didn't realize how big the load inside me was. By the time I got home, it stopped, but my beautiful panties were still soaked. "Hello girlfriend!" Cheryl greeted me at the door. "Hi." I tried to be nonchalant. I bent over to untie my dress shoes, when Cheryl came up and rubbed her hand on my ass. "Why are you so wet there?" She demanded but didn't wait for an answer. "Take off your clothes!" With great trepidation, I started stripping. When I removed my pants, Cheryl immediately saw my sperm soiled panty. "What have you done?" Cheryl shouted at me. I was about to open my mouth. "Don't lie to me." Cheryl didn't wait for me to say anything. I looked at Cheryl cowering and ashamed. "You fucked Katherine, that slut boss of yours, didn't you? I was amazed Cheryl would remember her. I nodded "yes" in confession staring at the floor. "Good girl!" I heard. "Telling the truth is much better than telling me a lie." Cheryl said. "Don't you think so Katherine?" I looked up and saw Cheryl and Katherine standing beside each other. "Yes, we are VERY good friends." explained Cheryl. "I needed to have someone watch you at work." I stood there in awe of what was happening. "From now on, you will be Gina permanently." I looked at Cheryl with a puzzled look. "You will be Gina my executive assistant at the office." Stated Katherine. "With emphasis on the 'ass' part." they both chuckled. "And at home, you will be my girlfriend." Said Cheryl. I was so happy I started to cry like the girl I am.