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.