6 comments/ 38351 views/ 23 favorites Initial Crossdressing Adventures By: vjak19 Since the first article I wrote described the last time that I dressed as a woman was generally well received, I have decided to share some more of my story. To do that I will start the journey at the beginning and travel through to some of the first times that I ventured out into public dressed as a woman. For those that did not read my initial offering let me describe myself. I stand about 5'7" and weigh just under 140. I cycle, swim and run which allows me a plausible explanation of why I shave what little body hair I have off. Anyway, back to the beginning. As I mentioned my mom almost caught me masturbating in bed when I was 18 with my big sister's panties which lead me to wearing them under my boxer briefs to get to the bathroom. I immediately noticed that I and my cock enjoyed the silky, tight feeling from her bikini panties. After that incident, wearing sis's panties as I jacked off became a regular almost daily occurrence. After several months of this, I became curious as to what her other lingerie would feel like against my skin. I expanded my use of her lingerie to include silk slips, panty hose and nylons wrapped around my dick as I beat my meat, all done while wearing a pair of her panties. I found that I only liked to wear her silk, satin or nylon underwear as the cotton ones did nothing for my libido. Wearing a pair of panties had become necessary while I masturbated for me to reach orgasm. Luckily for me we shared a Jack and Jill bathroom where we kept our dirty clothes basket which allowed me easy access to her sweet nothings. One evening as I perused through her dirty clothes basket looking for the perfect panties in preparation for stroking my cock, I was severely disappointed to not find any available to wear. There was a pair of pantyhose and a silk slip which I secreted away for my pleasure later that evening. That night as I lay in bed wanking sliding her slip up and down my shaft, I just couldn't bring myself to fruition. I determined that I needed to feel the tightness of a pair of panties wrapped around me. Without a pair to wear, I decided to try on her pantyhose. I sat on the side of the bed, rolled the right leg up until it was similar to a sock and stuck my foot into the nylon cocoon. As I slid the stocking up my leg I couldn't believe the feelings running through me. I got just over my knee before repeating the process with my left leg. Once I had both legs into the panty hose and above my knees, I stood up and pulled them the rest of the way up my legs, over my ass and cock. OMG, I can't tell you the intense feeling of being wrapped in nylon felt like, only to be heightened when I lay down and slid into bed. Feeling the sheets glide over my legs and butt was unbelievable. I took sis's slip and rubbed it against my encased swollen cock and in just a couple of strokes I blew my load, messing myself and my sister's pantyhose. I grabbed the washcloth that I usually shot off into and stuffed it down the front of the pantyhose cleaning myself as best as possible. I didn't want to take them off yet! Being a horny teenager and extremely excited my cock was still rock hard. I'm not sure why I did it but I decided to pull her slip on over the pantyhose. I guess since it felt so good just rubbing it up and down my pantyhose covered cock that I wanted to see what it would feel like on. Anyway, I worked her slip up my nylon swathed legs and over my ass. Unbelievable! As I rolled around in bed feeling the silk glide over my nylon covered lower half the feeling was indescribable, on my cock and my ass. It's no wonder women enjoy dressing up with this type of sexy feeling being generated just by wearing the lingerie. In no time at all I was depositing my second load in Audrey's (big sister) nylons. Still I remained stiff as a board. I needed to go clean up in the bathroom but didn't want the feeling to go away. Being too nervous to take the chance to walk across the room wearing Audrey's pantyhose and slip, I reached for my sweatpants and pulled them on over the top. The short trip to the toilet was exotic. The strange but wonderful feeling of my pantyhose covered legs moving around inside my sweats, my ass sliding freely back and forth and the silkiness of my feet floating across the carpet was a heady experience. Once in the bathroom, I quickly locked both doors and removed my sweatpants. My intentions were to remove my sister's lingerie, clean it up and go back to bed. When I dropped my pants and saw myself in the mirror, well my best laid plans went astray. I couldn't believe how good my legs and ass looked in her underclothes! My cock was rock hard thinking about fucking that hot thing in the mirror. I just had to walk back and forth to see how I looked as I moved. My walk turned into more of a sashay with my hips swinging doing my best imitation of some of the girls I'd dated. The slip was slithering back and forth across my ass and cock. The feeling was amazing. For the third time that night I came, this time without even touching myself. Reality forced me back to earth. I stripped out of these lovely items and spent some time in the sink washing and rinsing Audrey's pantyhose and slip. Using a blow dryer, I got them basically dry and put them back in her laundry basket. As I lay in bed unable to sleep, thoughts were running through my head. "Was I gay?" No, I really liked women and enjoyed their bodies, had no interest in men or their bodies. "I must never put on Audrey's clothes ever again." No way that was going to happen, I was too horny and it felt too good. "Wonder what her other stuff feels like?" Can't go there, I'm not gay, don't want to be a woman but did it ever feel good to dress like one. Eventually I fell asleep and had sexy and erotic dreams through the night. As luck would have it, my family was going to the lake for the weekend and I could not afford to miss swimming practice and it was necessary for me to stay home. Unfortunately, my girlfriend also was going out of town with her parents leaving me to satisfy my own needs. Friday night after my family had left it did not take long for the desire to put on a pair of sis's pantyhose and pull on one of her short, tight silk slips to enter my mind. My manhood was hard as blue steel just thinking about it. Striking out in the dirty clothes hamper did not deter my thoughts. I went directly to Audrey's room, pulled all the shades down on her windows and found her panty, sock and lingerie drawers. I was in heaven. I stripped out of my clothes and immediately began trying on all her different types of panties, but only the silk, satin or nylon pairs. I found that I enjoyed the feeling of her thongs as they squeezed between my ass cheeks but my favorites were her silk string bikini ones. The wonders in the next drawer not only included pantyhose but a myriad of nylons and garter belts. These too I tried on learning that although I really liked the way that pantyhose encased my legs and ass, a pair of lace trimmed thigh highs and a garter belt just felt more sexy. The next drawer of delight included her slips and bras. It didn't take me long to select a short silk lace trimmed black slip to slip on. I felt incredible and paraded myself to the mirror to have a look. The only way that I could describe myself from the waist down was as a sexy, hot woman on the prowl. I decided to go a step further and went back and tried on several of Audrey's bras. Even I knew my sister had a fine rack on her. Her proud 36C's did not go unnoticed nor did they lack for fine coverings from her drawer. I chose a black Victoria Secret bra to put on, stuffed each cup with a pair of her panties and went to look in the mirror again. Not bad but not great either. As I waltzed around her room I found myself acting more feminine. My desires were still running unchecked so the next place I checked out was her closet. I selected several short and very tight skirts to model for myself. I found it extremely difficult to get her skirts up without my slip riding way up. Eventually I would just put the skirt on, flip it up over my waist and then pull the skirt back down. The mini-skirts were followed by several tight fitting tops. Once completely dressed I took several more strolls around the room stopping and admiring myself in the mirror. I just had to find a pair of heels to try. My sister's foot was too small for me to wear any of hers so I headed to mom's room. I was lucky enough to find a pair of 3 or 4 inch heels that I could slip into. Trying to walk back to Audrey's room was comical. I couldn't figure out how a girl could walk in these much less dance or anything else but when I saw the way that they made my calves and ass look under that mini, I knew why they bothered to figure it out. I spent the rest of the weekend wearing different outfits, strutting around in high heels and constantly masturbating. I even started experimenting with make-up, mascara, eye liner, eye shadow, blush, nail polish and of course, lipstick. I found that I could make myself look plausibly sexy. Needless to say, I was hooked on wearing women's clothing but only to heighten my self-pleasuring. Graduation meant a summer off and then away to college. Moving into college meant living in a dorm with another freshman and essentially no privacy. It also meant that my sister's clothes were no longer readily available to me. Over the summer I had pirated away a couple pair of panties and nylons along with a garter belt, bra and slip. I kept these sexy items well hidden from my new roommate. Unfortunately, I only had the opportunity to feel these intimate items against my skin on the rare occasional weekend that my roomie returned to his hometown. This wasn't too disturbing since I had met a local girl who was attending the university as a day student. Sherry was just slightly shorter than me, very fit as she played soccer and like me was a swimmer. She had long legs, excellent butt and a nice handful of tits. It was only the 3rd date when we ended up in her parent's basement fucking each other's brains out. Turns out that she was as much of a horn dog as I was. Whenever the opportunity was available we would be naked and taking pleasure from each other's body. The only issues were finding a private place to partake in our love making and the fact that I was terrified of her father. Sherry's dad stood 6'3", weighed 225 and was very protective of his little girl. The first time I picked her up for a date he looked at me and said, "I want you to know that I haven't forgotten what a young man is thinking about and that before you do something that I'll have to make you regret, understand that I cherish my little girl more than anything else." Of course he said this to me when Sherry wasn't in the room. While being afraid of her dad, it didn't stop my desire to get into her pants. The Friday night of our third date coincided with my roommate being gone. Sherry and I went out to one of the local clubs and with our fake id's we were admitted and had a great time dancing, drinking and chatting. When I asked if she wanted to go back to my dorm room with me she didn't hesitate. Back in my room with our tongues wresting for dominance and my hands roaming freely over her tits and ass I made the big move and slid my hand down the back of her pants. I was prepared to remove my hand depending upon her reaction. I needn't have worried as Sherry's reaction was to unbutton her jeans and slip her zipper down giving me free access to be in her pants. I wasted no time and inserted both my hands and cupped her silk covered cheeks in my hands. Once again, the smooth sexy feel of a silk covered ass overtook my senses. It wasn't long until I had undressed Sherry down to nothing but her panties. I loved the way her pussy and ass looked and felt covered in the red silk of her underwear. My hands caressed and enjoyed every part of her body. Before long we were bumping uglies so to speak and I had totally forgotten about her big dad. Anyway, as I said before we were hot for one another and the only thing that interrupted our getting naked was finding a place. One place that was occasionally free was her parent's house which had a nice finished walkout basement. Obviously, I was always on edge whenever we would fuck down there. One fantastic fall day we were finished with classes and took a walk through the park. We stopped and started making out. Both of us were extremely horny and Sherry suggested going to her house as her parents were both working that day. Of course I agreed although I was uneasy. Once in her basement we started making out on the couch. I reached down, unbuckled her shorts and pushed them and her panties down off her ass and legs onto the floor. Her t-shirt and bra came next, then my own shorts, boxer briefs and t-shirts. Insert cock and away we went. I was stroking in and out of her tight pussy while trying to work my tongue down her throat when we both heard a door slam and her father call out for her. PANIC and I mean PANIC plus adrenaline rushed through my body. I jumped up and into my shorts, grabbed my shoes and t-shirt and was out the basement sliding door in less than 10 seconds. Sherry grabbed her shorts and top and darted to the downstairs bathroom while answering her dad. Once outside, I buttoned and zipped my shorts, pulled my shirt over my head and slipped into my shoes. Over one fence and into the alley and I was fast walking away from her house with my heart beating a mile a minute. I'd gone about 2 blocks when I felt a vibration in my back pocket. Reaching back I found my phone, curious as I always carried my phone in my front pocket, and pulled it out. It was pink, Sherry's phone, and I was calling her. My brain wasn't working right do to the adrenaline still coursing through my veins. I answered Sherry's phone to find Sherry calling me. She was laughing hysterically and said "Well?" I said well what? "She said did you figure it out yet brainiac?" "How does it feel?" "Bet you look sexy!" All while laughing her brains out. I told her to quite messing with me, that I had almost lost my life. Sherry said, "Calm down, daddy only stopped home to pick up his jacket as he and mom are going to dinner straight from the office tonight. He never suspected a thing." "Now think about it, does something feel different." It was then that I finally used my big head and put 2 and 2 together. Looking down I noticed that "my" shorts were really short and my underwear felt awfully smooth and silky. Duh, I had jumped into Sherry's shorts and underwear during my panic exit. My prick was immediately rock hard. I was transformed back to Audrey's room and all her sexy clothes. "Hey are you still there?" This brought me back to reality. Here I was in an alley wearing a pair of sexy bikini panties and short shorts holding a pink phone to my ear with my girlfriend talking to me on my phone. Sherry said "Get back here and finish what you started; besides I want to see that tight ass of yours in my shorts and panties." I hustled back to my gal's house feeling very self conscious of what I was wearing and slipped into her basement by the same route that I had just exited. When I went to put my arms around the laughing Sherry, she pushed me back against the wall. She said, "Hold on a minute sister, I want a good look at the merchandise." She told me to walk back and forth across the room and then to spin around for her. She commented, "I seriously think those look better on you than on me." "Doesn't matter, you're mine now, drop those shorts and get over here and make me feel good." I quickly dropped her shorts and panties and walked over to her on the couch. Sherry said, "I think somebody liked wearing my clothes, I've never seen your cock so big or so hard." "Get down here and put it to use." I drove my cock deep into her and pounded her with no remorse. After about 10-15 minutes I felt the familiar pressure building and quickened my pace even more. With a final deep stroke I emptied my balls deep into her hot hole. Sherry looked up at me and said, "That was unbelievable, we need to do that more often." "What are you talking about, we fuck all the time" was my response. She just looked up at me with a wry grin and said, "You know exactly what I mean." We stayed cuddled together enjoying the post love making relaxation. After a bit Sherry said I've got an idea, promise you won't get mad but I want to try something. With that she pulled me to my feet and said grab your stuff and come with me. Together we went upstairs to her room. Once inside her bedroom, Sherry said, "we aren't able to spend any nights together but daddy doesn't mind when one of my girlfriends spend the night." She became a whirlwind of activity. Sherry started pulling open and grabbing things out of drawers, going to her closet and bathroom and finally having me sit in her dressing chair. She told me to stay with her and not to get mad or hung up on anything until she was totally done. With that my little minx started applying make-up to my face. Once finished painting my face, she handed me a pair of red nylon string bikini panties and told me to put them on. Next she pulled a pair of jet black shear to the waist back seamed pantyhose off her bed. She told me to raise first one leg then the other and she worked the stockings up my legs until she had them above my knees. She then had me stand up, and started pulling the nylons further up my legs. My cock was rock hard and poking out of her panties. She gave me funny look and said that it looked as though I was enjoying myself and that we would have to take care of my excitement. She bent down and swallowed my cock to the root. She bobbed up and down my rock hard schlong until I blew my load into her mouth. She took every drop, rose to her feet, locked lips with me and stuck her tongue into my mouth. I could taste my own cum on her tongue. Sherry tucked my package between my legs and worked the pantyhose over my bum, adjusting the back seems to be straight up my legs. Next she picked up a skirt and pulled that on me as well. It was made of denim and I think spandex, so it clung to ever curve on my body. Next came a white bra, which she hooked for me and then adjusted the straps for fit. To my surprise, well to be honest this was all to my surprise, she then slipped in a pair of breast forms. I asked her what they were and she told me that she was a late bloomer and had used them to enhance her look when she was younger. The next item she put on me was a semi-sheer white blouse that just allowed for a shadow of the bra to show through. Sherry then rummaged through her closet and came back with a pair of 4" strappy heels. She opened the straps as far as they could adjusted, slipped them on my feet and told me to be very careful that these were fairly high and walking in any heels took a lot of practice much less ones this tall. She then turned me around and had me look in the mirror. I couldn't believe it, looking back at me was a very attractive woman except that her hair cut was in a man's style. I spun around and quickly walked across the room to her full length mirror to be able to see the entire outfit. Once in front of the mirror I turned first one way then the other before quickly strutting back over to Sherry and gave her a hug. Sherry was looking at me very critically. I was wondering what I had done to upset her when she said, "This isn't your first rodeo is it mister?" Oh shit, I had gotten so excited that I had forgotten about the heels and had just sashayed back and forth across her room like I had been wearing high heels all my life. Sherry said, "Well." I stumbled and bumbled my way through a plausible cock and bull story about my sister playing dress up with her little brother and a costume party contest in high school. Sherry seemed to at least accept the story. She just said we need a couple more final touches to complete the ensemble. Initial Crossdressing Adventures With that she clipped a pair of gold hoop earrings on my ears, added a bracelet to each arm and then went deep into her closet to come out with a brunette shoulder length wig. She put the wig on my head, used several bobby pins to secure it and brushed it to a fine luster. She said, you look so good that I'd be the competition if we were to hang out at the bar together. Then she said, "My dad will have no idea. Dressed like that you can spend the night with me whenever we want." I took a big gulp. Fantasy was one thing; trying to pull this over on her father didn't sound like a good idea to me. I thought that I looked passable but thinking and believing are two different animals and I told Sherry as much. She started sweet talking me, telling me how much she wanted to wake up in my arms, how she wanted me to wake me up by sucking my cock. This was having its desired effect on me but I just couldn't get over getting caught dressed as a woman. Sherry finally said, "Listen, you've been trying to fuck my ass and I've always said no." "If you agree to truly finding out if you pass the muster as a girl, I'll agree to let you take my virgin butt." She had just made me an offer that I couldn't refuse. I said, "Okay, but not in front of your dad, it will have to be somewhere that I'm not known." With the deal having been agreed upon we made the decision to visit a bar/club the next town over on Friday night. Outwardly, I acted perturbed but inwardly I was excited as all hell, nervous but excited. The week couldn't go by fast enough. The week finally drew to an end and Friday my roommate jumped into his car and headed back to his hometown. Sherry came to my dorm with a small suitcase. I was so horny I threw her on my bed and ravaged her. Once I was satiated, she said it's time to get going. First she made my face up, secured the wig to my head and proceeded to dress me similar to the way she had before except that the skirt was a little shorter. We were all set but I was scared stiff. This was my dorm and how was I going to get out of here without getting caught. Sherry said don't worry, I'll clear the way. She went out and pulled her car to the back door. She then came back to my room and let me know that the hallway was clear. I took a deep breath and followed her out the door, down one flight of steps and down the hallway to the back door. We were about halfway to the door when I heard a whistle and someone shouted, "Holy shit, hey ladies why don't you come to my room?" Sherry and I just picked up our pace and were soon out the door. Sherry was laughing her ass off and telling me that was your proof right there. "Didn't you hear, that guy wanted you?" Getting into her car was an experience that I'd never contemplated. I'm sure if anyone was looking that they got an eyeful of my legs and up my skirt as I negotiated sitting down in her passenger seat. I worked my skirt down to a respectable mid thigh length. I told her that he was after her and not me. She answered BS, you'll see in a little while. With that she drove away heading to the club in the next town. She told me that she would call me Cindy. We had a plan that if I was to be found out we would blame it on a fraternity initiation haze. Regardless, my nerves were raw as we drove the 30 minutes down the interstate. We finally arrived at the club and parked the car. Sherry told me that when I opened the door to keep my knees together, pivot in my seat and swing both feet out at the same time. I did as she said and was able to extricate myself out of the car without giving a peep show. As we came around the building and approached the door I had another panic attack. They were checking identification at the door. Sherry told me not to worry, that we would tell the guard that my purse had been just been stolen and I needed a drink to relax. She said that and a little flirting should work the trick, if it didn't, she said I had at least tried and we could go back to my dorm and she would give me her dark hole. Nothing ventured, everything to gain, I followed Sherry up to the door. She started explaining the situation and it felt as if the guard wasn't going to go for the story. He kept shaking his head back and forth. Sherry's purse slipped from her hand and hit the ground came open and a couple of items spilled out. She said, "Cindy could you grab that for me?" I bent over and picked up her lipstick, compact, cell phone and purse. I was putting everything back into her little purse as I gathered them. It was about then that I realized that my already short skirt had risen up until it was at the bottom of my ass cheeks. I blushed to the core, straightened up and handed Sherry her purse while the guard just looked at me and told us to go on in and enjoy ourselves, he was sure that I had the credentials to be there. We got inside, went to the bar and ordered a couple of drinks. I ordered a beer and while the bartender was getting our drinks Sherry said at least drink it from a glass. Oops! We found a table towards the back and perched our asses on the chairs. Sherry told me that she about lost if when I flaunted my ass to the bouncer to get admitted to the club. I told her that it was totally unintentional. She said unintentional or not it was highly effective sweetie, but you'd better learn to keep your knees together or cross your legs as we sit here, there is no reason to give everyone a free show. We sat there for a little while listening to the music, talking away and I began to relax. I actually started to forget that I was dressed as a girl. When we had finished our drinks, Sherry told me to go to the bar and get us another. She handed me some cash and I sauntered up to the bar, this time for two glasses of wine. I placed the order and when the bartender set the two glasses on the bar I tried to hand him the money and he shook his head and nodded at the gentleman next to me telling me that he had bought them. He introduced himself and asked if he and his friend could join us at our table. I stuttered that I guessed it would be alright. The three of us walked over to the table and Sherry was sitting there with a smirk on her face. I sat down next to Sherry and the guys sat on either side of us. There was the usual get to know you conversation and the guys were using some lines on us. Sherry then shocked me and reached over and started holding my hand. She then said, I need to go to the powder room, Cindy do you want to go with me? We both got up and excused ourselves, Sherry grabbed her purse, and we headed for the bathroom, the girls bathroom. Sherry was whispering in my ear that she had told me so and that she knew I'd be tough competition. She had slowed down and told me that you know the guys are watching our asses as we walk don't you? Having said that she let go of my hand, put her arm around my waist and dropped her hand onto my ass, giving it a good squeeze. I jumped a little not expecting anything like that to happen. My little minx just started giggling and asked how did I like being a girl, this is what happens you know. She stopped us just before we went out of sight of the guys, spun me around to face her and pulled my face down to her. Her lips meet mine; her hands went around my back and cupped my ass cheeks as her hot tongue forced its way into my mouth. She kissed me with wild abandon. Sherry broke the kiss grabbed my hand and pulled me into the ladies restroom. She was laughing her ass off again. She said that she needed to show the guys who I belonged to before they got to many ideas. With that she directed me to a stall telling me to sit down to do my business. We finished going to the bathroom and Sherry freshened both of our lips with her lipstick before returning to the table. The guys were waiting on us along with another round of drinks. We continued chatting and flirting with the guys but Sherry always was either holding my hand or had her arm around me. Sherry and I even got up and danced a couple of songs together. Dancing in high heels is both work and a workout. The guys joined us for one song and then a slow song came on but we told them that we wanted to go sit back down. Once again there was a new drink for us. It was getting late so we finished our drinks and said goodbye to our new friends. When we stood up the guy closest to Sherry leaned in to kiss her but she deftly moved her head, so instead he just pulled her into an embrace and pecked her on the cheek. I was unsure of what to do but my guy wasn't as forward and just asked for a hug. I said sure and opened my arms as he enveloped me with his big arms. He hugged me tight and told me that I felt and smelled good. At the last moment one of his hands reached down and gave my ass a pat. I broke the hug, Sherry grabbed by the arm and we waltzed out the door with her laughing away like a hyena. She was telling me I was some kind of flirt. We hurried back to my dorm room. Sherry parked the car and went in first to make sure the coast was clear then waved at me to come on in. Sherry had my keys and as we got to my dorm room as she was putting the key into the lock, one of my floor mates came around the corner. He asked what are you two girls doing going into Craig's room. Sherry turned to him and said surely you recognize me Mike, I'm Craig's girlfriend Sherry. Mike response was still what were we doing here. Sherry said, I've brought a friend with me and we want to surprise Craig, is that alright? Mike just shook his head and said some guys have all the luck. This entire time I was shitting bricks scared that I would be recognized. Sherry opened the door and allowed me to go in first. Once inside she started cracking up, telling me that she knew I'd pass as her girlfriend. She started kissing me and fondling me asking "How do you like it?" Then she said, "An agreement is an agreement, get some lube and be gentle with my ass." I finally got to tap her fine ass. We had a great night screwing our brains out and I'm sure my floor mates thought I was one lucky dude spending the night between two hot women. I know that over the next few days whenever I would see one of my dorm mates would see me they would get a big smile on their faces, a couple even high-fived me. We spent the next couple of weeks going to classes, hanging out and of course fucking whenever the opportunity was there. I even got to enjoy Sherry's fine ass again. Only having the odd opportunity to get flesh to flesh was frustrating. My gal made the suggestion that I spend the night with her at her house. I was concerned, very concerned, about her dad but Sherry said, look, you fooled the guys at the club all night long; all you will have to do is walk past my dad on the way to my room and maybe again when you leave, no more than 20-30 seconds. No big deal. Well, the little head overruled the big head. Now the problem was to find a place for me to get "dressed". We wound up with Sherry doing my makeup and wig in the back seat of her car while parked in the rest area just outside of town. From there, we walked into the women's restroom where I went into a stall and changed out of my jeans and t-shirt into my women's clothes for the night. This night I put on a pair of blue string bikini panties, next came a pair of Sherry's white almost translucent pantyhose, her blue satin bra with the breast forms, a blue silk blouse, a black mini skirt and a pair of 3" strappy heels. I strolled out of the bathroom with my other clothes in a plastic bag and together we made our way back to Sherry's car. Sherry had already called home and okayed it with her parents that she was bringing a girlfriend home to spend the night and that another girlfriend might stop by later. The latter was just some additional smoke screen to make it sound like a slumber party. We headed to Sherry's house with me extremely nervous. We parked in the driveway and headed for her front door. She opened the door and ushered me in. I stood just inside her doorway allowing Sherry to lead me to her room. We walked past the family room where her parents were watching television. Her mother asked Sherry to introduce her friend, to which she said, "Mom, Dad, this is Cindy, we go to school together." Sherry's mom started with the general banter of how are you, how do you like school, etc. I tried to answer her questions but couldn't help but notice that Sherry's dad was staring at me. I thought I was busted for sure. Sherry pulled me away to her room telling her mom that we were going to watch some television, try on clothes and gossip. As I was walking down the hallway I overheard Sherry's mom telling her husband that he shouldn't be staring at their daughter's girlfriends. Sherry closed the door to her room and I nearly collapsed my legs were so weak. We had gotten away with it, so far at least. Through the rest of the night and even when I left early the next morning there were no problems other than one incident of her mom knocking on the door and telling us to "Hold it down" while I had my cock buried in her hot snatch. While this was exciting and fulfilled our carnal needs it wracked my nerves. It also didn't solve the other issue of being able to go out and have fun. As a non-scholarship student, I had to work a steady job to be able to stay at the university. With school taking up most of my money, there wasn't a lot in the pocket to take Sherry out for some of our favorite activities, drinking and dancing. I had taken this dare/bet/proposition essentially as a one-time action, with perhaps a couple of replays to get me into Sherry's room and hot pussy while her parents were home. I never thought about going out in public again even though the thrill was an indescribable rush. One weekend evening we were sitting around my dorm really wanting to go out but unfortunately my finances were not up to the task. Sherry said "Why don't we go out as girlfriends?" She said "We have fooled the guys at the club before and my parents we can do this." I brought up the whole driver license issue and getting into the clubs. This was an easy fix in the college setting as we both knew of a guy that made fake ID's from a mural he painted on the wall in his room. All you did was put in your vitals and stand against the wall with your head at the photo location. He took a picture and worked his magic on his computer and printed you a very convincing driver's license. Once laminated it was good to go. The entire process was less than 15 minutes. So once again I found myself in the backseat of my girls car having her apply make-up to my face and attach her wig to my head before again going into the women's bathroom to change. Once done there, we were off to get my fake ID. Our cover was that I was a cousin of Sherry's from out of town and just underage. Once we got there, Sherry did all the talking and negotiating. She agreed that we would write a term paper in lieu of paying for the ID. That with some flirting and I had my pass to the clubs. Off we went to the same club that we had gone to before. We had fun, danced, drank a lot of free drinks purchased by guys and eventually went back to our town. We had so much fun as girlfriends that we decided that we should do this more often. My dressing as Sherry's girlfriend and us hitting the clubs became nearly a weekly thing. We seldom paid for admission or drinks while at the clubs. I became very comfortable dressed as a woman. Guys continued to hit on both of us. We both loved flirting and more than a couple of times I had to remove a guy's hands as they traveled over my legs and ass. At one club we had become sort of known. It was at this club that Sherry and I were at on a Friday night. We had a three day weekend and the plan was for us to have some fun there and then go back to her house for another sleepover. On this night I was wearing silver Victoria Secrets silk panties, black stockings with a black garter, a black silk lace trimmed slip with a tight black tube mini skirt. I had a black bra on under a white semi-sheer blouse, silver hoop earrings, silver bracelets, a wide silver sequined belt and a pair of 4" silver pumps. We were partying hard, dancing our ass off and being approached by a number of guys on and off the dance floor. On the dance floor one guy had his hands on my hips and pulled me back against his crotch while we were fast dancing. Sherry was dancing with another guy who had also pulled her back into his groin and she was grinding her sexy ass all over him. I decided two can play that game and starting really bouncing my ass against him and felt his cock start to rise. Sherry and I locked eyes and gave each other a smile. She turned around and faced her guy and started dry humping her hot pussy on his leg. Not to be out done, I followed suit being careful to not dislodge my well tucked cock. Next, Sherry again turned and was working her ass against her guy's hard cock. I quickly followed her lead and again was gyrating my ass against my guy's now big cock. His hands went from my hips to slide up and down the sides of my legs while occasionally running over my hips. This had become a contest between her and me. Sherry looked at me, blew me a kiss, turned around to her guy, tilted her head back and planted her lips on his. It was very obvious that she had her tongue in his mouth. His hands were cupping and groping her cute ass which was working her tight skirt up. I think it was seeing her stocking tops start to show that made me realize that something similar was happening to my own skirt. My guy (Jim) had worked my skirt up to the very bottom of my ass cheeks. I turned into him and I think he thought that I was going to kiss him as well but I turned my head and put it on his shoulder. He wasn't to be denied that easily and started kissing my neck and nibbling on my earlobe while both his hands had a grip on my ass. I told him that I needed to sit down and headed back to table that Sherry and I had secured. He followed, held my chair for me and then went to the bar for more drinks for us. He brought back a cocktail for me, a beer for him and two shots of tequila. I was looking around for Sherry but did not see her on the dance floor. Meanwhile Jim had returned with the drinks. I was surprised at the shots, already fairly drunk, but didn't know how to turn it down. Jim sat down, made some silly toast and we both downed the shots. He then pushed my drink towards me and told me to drink up. He put his hand on my leg, which I quickly removed. We continued drinking and the alcohol must have been taking effect on me because I suddenly became aware that Jim had put his hand on my knee and was stroking my stocking covered leg and I hadn't even noticed. I asked Jim where Sherry went and he said that she had stepped outside to get some air with his friend Bill. He asked if I wanted to go out and get some fresh air too and see if we could find them. I must admit I was feeling a little jealous having seen Sherry kiss Bill and agreed to go outside with Jim. Once outside, we looked around for Sherry, eventually going out to the parking lot. Jim had his arm either around me or his hand on my back the entire time. In the parking lot out back Jim said that he and Bill had parked over in the corner. Jim pointed out their two cars saying his was the red one and Bill's was the yellow one. They were parked a couple of rows apart and we had to walk past Jim's car to look in Bill's. As we approached the yellow Chevy I noticed that there were two people in the front seat. My alcohol numbed mind thought, so that is where Sherry is. As I got close I was able to see that these two were in a heavy necking session and that one of Bill's hands was squeezing Sherry's tits while the other was up her skirt. I immediately got jealous and turned around and started walking away. Jim had seen exactly what I saw but where I was jealous he was turned on. He kept his hand on my back and directed me over to his car. Initial Crossdressing Adventures Not sure what I was thinking, other than seeing my girlfriend making out and being felt up by another guy, but when Jim opened the door I allowed him to guide me into the backseat. He told me to scoot over and sat down next to me. He asked me if I was alright to which I wasn't able to answer. Jim had put his arm across the back of the seat which put it around my shoulders. My skirt had risen up to my stoking tops. Jim turned and faced me all the time talking to me about how sexy, how hot, what a good dancer I was and how I was driving him crazy. I said something about having to get Sherry and go home and he responded "She's having a good time, so should you." Jim had put his other hand high on my leg and was stroking from my knee to my stocking top. With his other hand he was massaging my neck and playing with my ear and hair. He turned my head to him and the next thing I knew was he was kissing me and trying to stick his tongue down my throat. I know the alcohol played a part but I was responding to his hot kiss. While he was playing tonsil hockey with me his other hand was working its way under my skirt. I guess he thought if his buddy was getting some that fast he was getting some as well. When his hand hit my bare skin under my skirt, I snapped back to reality. I tried to pull my lips from his but he had a firm grip on the back of my head. I used my hand to grab his and pulled it out from under my skirt. Jim got a little aggressive at this point and tried to go under my skirt again. I stopped him again. He broke the kiss and was clearly upset. He said, "What are you just a big cock teaser?" I was scared I was going to get found out and either be made a fool of or get the shit kicked out of me. I wasn't quite sure how to get out of this situation. I told him that I was embarrassed that I was on my period. Jim relaxed a little with that and again kissed me. This time he took my hand and put it on his hard cock. He started working my hand up and down his jean covered rod. He kept working his tongue in my mouth and his hand that had been holding my head slide down and started rubbing my ass. Jim took my hand and brought it to his chest. I wasn't sure what he was doing until he brought my hand back to his cock which was no longer contained in his pants. He put my hand on his hard member and started jacking himself with my hand. I had never touched another man before. Now I'm in the backseat of a car with some guy that I just met kissing him and beating him off. How does an all American boy wind up in this situation? Jim let go of my hand and I continued to stroke his shaft. His hand was now trying to unbutton my blouse; well actually he had already got a couple of button at the bottom unfastened. Once again I had to stop him before he found out I was not a woman. Jim reacted unhappily again. We both had drank a lot and he wanted what he wanted. He again called me a cock tease. He grabbed my blouse and I was sure he was going to rip it off me. I was trying to push his hands off me and in doing so, slid down to the floor. This removed his hands from my top but hiked my skirt up to where my panties where showing and left me staring at his cock. Jim took this as a good thing. He said, "Okay, if that is what you want, I'm fine with it since it's your time of the month." My alcohol dimmed brain didn't compute until he put his hand behind my head and pulled my face right to his dick. The lights went on when his cock head hit my lips. Jim was saying "Come on baby, you want to suck it, show me how good you are." I saw no way out. I stuck my tongue out and gave his head a lick. I then licked the entire length of his shaft, roughly 7 inches long. I was using my hand and tongue but that wasn't going to suffice. Jim said, "Stop teasing and suck that cock baby." I opened my mouth and for the first time took a dick in my mouth. I sucked on the head and swirled my tongue all around it just like I enjoy it when Sherry does it. I then slid my lips down the entire length of his shaft. I was able to get it all in my mouth with gagging. I worked the entire length of his member bobbing my head. At the same time I was sucking as hard as I could and twirling my tongue around. After about 5-7 minute, Jim grabbed my head and drove his hips forward burying his cock into my mouth and started cumming. I hadn't planned on taking his spunk in my mouth but found myself with little choice as he pumped five or six squirts into my oral cavity. I couldn't hold it all and his cock so I was forced to swallow it as he was ejaculating. After Jim was done shooting his load into my less than willing mouth, he stroked another 4-5 times before pulling out. He told me that I gave great head, really, has anyone ever had bad head! Jim tucked his cock back into his pants and said "We should get back inside." With that he opened the door to climb out, leaving me half on the floor with my skirt over my ass and my panties showing. My blouse was untucked and had a couple of button undone. I scrambled out of the car pulling my skirt down. Jim said, "You've got a fine ass." Jim started for the club but I need a few more moments to compose myself and make myself presentable. As Jim and I came to the entrance of the club I noticed the doorman had a smirk on his face. I walked in and immediately went to the table looking for Sherry. She was sitting there with Bill and when she saw me she went white. She got up and ran to me and said "Cindy are you all right?" She dragged me off to the bathroom and asked me what had I been doing, that I looked a mess. When I got into the bathroom, I saw what she was saying. My hair was a mess, my blouse not properly tucked in, the seams in my stockings no longer straight, my lipstick smeared and a little bit of cum on the corner of my mouth. I told Sherry what I saw her doing with Bill and what all had happened, well nearly all, of what happened with Jim and I. She told me that she was kissing Bill but stopped him from doing more and what I must have seen is just as she was stopping him from groping and fingering her. After fixing our faces we decided to call it a night and made our way out of the bar. The doorman asked us, more me, if we had enjoyed ourselves tonight. Sherry answered with a smile, "I know I did and I think Cindy did as well."