Tina and Rick - Part 1
During my first year in college, I stayed in an all male dormitory. Because I was about a year younger than most people starting college, some do-gooder floor advisor decided to pair me up with an older roommate. Rick was about 12 years older than me and was not a particularly good role model. He was returning to college for at least the 3rd time, he drank a lot, he gambled, he had a bad temper, and he was overbearing and rude. Rick constantly amazed me, hitting on an endless stream of women in local bars with a constant barrage of horrible, crude pickup lines. If he ever managed a first date, he rarely managed a second date with the same woman. I think Rick enjoyed having me in his room because I catered to him a bit. If he told me to get him a beer, I would get him a beer, and so he was nice to me even though he griped about me to everyone else on the floor.
There were huge theme parties in our dorm at least every second weekend. A lot of the guys had dates or just hooked up with girls they invited from class. Rick tried to pick up other people's dates, occasionally causing some of his friends to get angry with him. I was pretty shy, and not particularly interested in dating, and so never had dates. Although Rick never brought a girl to the parties, he was fond of telling other guys that I hadn't gone through puberty yet, and he would grab my face and point out that I couldn't grow whiskers. I was well past puberty but definitely couldn't be described as overly masculine. About midway through the semester, someone decided we needed to have a "pimp and prostitute party" to get the ladies to show up in skimpier clothes. We had been to a pimp and prostitute party at another dorm, and I had been stunned at how slutty some of the girls' outfits were.
It was right about this time that it dawned on me that it would be just one more party at which I wouldn't have a date, and at which Rick wouldn't find a date. Rick was drinking some beer I had bought, and so he was in a pretty good mood when I told him that I was thinking about dressing up as a female prostitute for the party. What I didn't tell Rick was that while living at home, I occasionally snuck clothes and makeup out of my two older sisters' bedrooms and completely dressed up. In fact, my oldest sister once told one of her boyfriends that I looked more like a girl than a boy, and then proved it by doing a complete makeup job on my face. In fact, it would have been more accurate to say that I looked like an attractive girl when I was dressed up.
As luck would have it, Rick's sister, who was just a couple years younger than Rick, showed up to visit Rick on the night of our last party before the upcoming "pimp and prostitute party." Anne was the exact opposite of Rick. She was sweet, gorgeous, very sexy, and every guy flirted with her at every opportunity; she has the most incredible legs and a beautiful face. Of course, Rick had to immediately tell Anne that I was planning to attend the next part dressed as a hooker. Rick and I obviously had a very different mental image of what I was going to look like; Rick thought I was going to look like something from a cheap comedy movie, I was hoping to be 110% passable on party night. Anyway, Anne and I talked way into the night and quickly became friends; Rick fell asleep somewhat less than sober. Anne headed for her hotel, but returned late the next morning to whisk me away with her for a 3-day shopping weekend. As we left, Rick said, "You girls have fun!"
By the time we reached Anne's house on Friday night, we had shopping bags and boxes containing at least the following items, for me: pink strappy highheels, a crotchless nylon body stocking, a nude firm control body briefer, packs and packs of black nylons and fishnet thigh-highs, a shoulder length dark brunette wig, and what I felt were "way too big" breast forms we got on half price. Anne provided me with supplies and sent me to the tub to shave my legs (this was a first), to shave whatever traces of hair I could find on my face, and to lotion down with baby oil. I had been a visibly shakey, nervous wreck all day long, but within a few hours of the time Anne finished supper, she had me in a body-shaping purple dress, high heels, pinned up brunette wig, perfect makeup, and ready for a public practice run. I had watched the step-by-step transformation in a full length mirror, and every inch of my body was shaking because I was thinking that I might already be "more than passable."
Anne went with me on the first practice walk down the long hall to the elevator and down to the parking garage and back. She told me I was a natural born high heel walker (hmmm?). Next, I went solo to the lobby to get her mail; and I felt like two guys coming into the building shot me some extra glances. I wasn't sure if the glances were a good sign or a bad sign, but they were definitely a new sign; I wasn't used to guys or girls looking at me. My heart was racing as I walked back to the elevator. Just as I stepped into the elevator, a young man stepped into the hall from the parking garage and raced over to get into the elevator with me. He said hello and there was absolutely no doubt; as he got into the elevator he stared... longingly... at my legs and boobs... he snuck at least half a dozen more peaks at my legs and heels on the way up to his floor, and he wasn't making much effort to hide it. I was literally ready to jump out of my skin by the time I got back to Anne's apartment.
The next night we ventured completely outside, with me in a pink sweater that accented the huge breast forms so much that it made me uncomfortable. I thought it made them look less real. Anne assured me that they definitely looked real, and told me what I already knew, that guys love huge boobs, so not to worry about it. I was in a pretty tight pink skirt cinched really tightly around my waist, black nylons, and of course my strappy hooker pink heels. It was already getting a little bit dark, which made me feel a bit more comfortable. We were about 50 feet out the front door when two guys on bikes rode by, turned back for a long second look, and whistled at us. On the very next block, a guy standing on his apartment balcony called his buddies out to check out the "excellent hookers" walking by. As I looked at my reflection in shop windows, I really started to accept that I was absolutely passable looking... in fact... pretty hot looking.
The message sunk in deeper as cars slowed down. This was still all new to me and my heart would not stop racing. Some of these guys were driving along beside us and literally pleading with us to get in their cars. One huge guy in a Caddy got mad because we wouldn't get in his car, called us bitches and drove off screeching his tires. I told Anne that I felt hot because we had too many clothes on; Anne told me I felt hot because I was nervous, and because I was horny and badly needed to suck off one of the guys that was trying to pick us up. Just then a cop car slowed down and crept along beside us (we kept walking); evidently I wasn't only passable, but I really looked like a hooker. We wandered around looking in shop windows and got more of the same.
Anne finally pushed me into going into a dark, very noisy bar. My feet were sore from the high heels. They were very comfortable when I put them on, but they pinch the front of your foot when you walk around raised way up on your toes for a long time. I was still a total nervous wreck. We walked in just far enough to reach the telephones where I placed a pretend call to Anne's answering machine. I looked in a mirror by the phone expecting that all of my makeup had run off, but it looked pretty much intact.
Anne's told me to stay on the phone and keep talking until the coin ran out. While I was on the phone, one guy came over and asked Anne what we would charge to go home and shoot some pool with him and the guys at his table (shades of Rick!). She answered him by saying, "there are too many of you, but come and talk to us after some of your friends go home!" Another guy who looked like he simply did not belong in the bar came over and started whispering with Anne. He walked off just as I finished my pretend conversation. I was ready to leave! Anne said, "We have to wait a minute, I just got us a ride home."
Sure enough, here came Anne's gentleman friend with a six-pack of beer. As he walked us toward his car, this nice guy handed us each a cold beer. He opened the front passenger door first, and Anne pushed me in and then slid in beside me. While our driver, Jim, walked around the car, she gave me a fresh coat of lipstick and told me to relax. When Jim slipped in beside me, his body pushed right up against me. We started driving while Anne and Jim chatted away. We had been driving for several minutes when I said, in my very best quiet female voice, "I didn't realize we had walked so far."
Anne replied, "We didn't, Jim is just looking for a spot where we can pull over and enjoy a beer." She then leaned over and whispered in my ear, "While you give him the handjob he just payed for. Want me to hold your beer?" I am now speechless as Jim drives around town and pulls into this parking area alongside the river where we have a reasonably scenic view. We are all sipping our beer now and Jim, whose right hand is sliding up and down on my left thigh, is telling us how pretty we are and Anne is telling him how many guys tried to pick us up tonight.
And then Anne casually says, "Jim, why don't you lean your seat back so you can relax?" Of course, the words are not even out of her mouth and Jim is sliding his seat back and tilting it way back. At this point, Jim obviously has a big, very hard erection in his pants and he is obviously staring straight at my boobs. Anne has opened a tube of hand cream and I think she is about to reach across and give Jim a handjob when she grabs my hand and squirts it full of cream. To help things along, Anne specifically asks Jim, "Do you want me or Tina to take care of you?" And thus I became Tina.
Gentleman Jim cautiously says, "Well, I want both of you to... or either of you... well, how about Tina?" So now I had to fish or cut bait as they say. And what happened next happened with absolutely no hesitation on my part, and proved to be the first time I was able to relax all that day. I unzipped his pants, and started to pull Jim's penis out of his pants, which was actually pretty difficult because his cock was already hard, and would not bend much, and as I was trying to work it out, he was responding by getting even harder.
I finally got Jim's cock out and started stroking him off. He was still rubbing my thigh but his hand was starting to wander further down my leg in search of my calf, and I suspect my very slutty looking high heels! I was really trying to focus on the head of his cock, which was obviously extremely sensitive. His cock definitely kept getting harder as I played with it and worked on it, and I soon found myself wanting really badly to lean over and see what that big hard rod would feel like to suck on, and to have him cum really hard in my mouth, but I was afraid he might grab my hair.
Jim was already leaking a lot (a lot) of pre-cum on my hands, and was definitely ready to cum, but I wanted him to get his moneys worth and so kept trying to slow down when his hips started pushing and he got moaning too loudly. His eyes were occasionally closing, and his right hand was no longer exploring my leg but had strayed up to my left breast. My left breast was inside a tight fitting one piece body briefer under my dress, and it definitely passed the test, because once Jim's hand was on my breast, he started rubbing the breast. By now, Jim's cock was extremely rock solid hard. He was trying to twist sideways in the seat and now had both his hands on my breasts and his hips were starting to push back and forth, as he literally began to fuck my hands. I wanted so badly to suck on his super hard cock, that I was trying not to let him cum while I tried to decide what to do.
Anne brought me back to reality while I was sitting there stroking up and down on Jim's cock with my hands, while Jim was slowly stroking my hands with his cock, when she said, "Jim, why don't you come back to our place and fuck the daylights out of Tina tonight?" Jim obviously thought about it because the instant she asked him if he wanted to fuck me, his cock ejected a big squirt of pre-cum over the back of my hands. At that very instant, I made a funny decision. I decided that the first guy that was going to fuck me was going to be my roommate Rick. Of course, Rick didn't know that, and I still had Jim's pretty huge, definitely hard, rapidly throbbing, cum-leaking cock in my hands. I squeezed one hand tightly on Jim's thick cock shaft and lightly grabbed his cock head with my other hand and started pumping really fast. Jim let go of my breasts and rolled flat on his back and started raising his hips off the seat as he got ready to cum.
I had also just made the decision to wrap my mouth around Jim's huge cock, and suck every drop of his load out, but it was already too late. The very instant I started moving closer to his penis so I could suck him off, he blew the biggest load of cum that I had ever seen. There were cum spots on the car window (really!), there was cum on my face and in my hair, there was cum on my dress, there was cum running on my hands as I kept pumping, and by the time I managed to get his huge cock head into the back of my mouth, a few remaining slurps of cum continued to ooze out of his gorgeous big cock, which felt warm, huge, hard, and cum-covered in my mouth. While Anne kept telling Jim how wonderful his cock looked and how spectacular his orgasm was, I sucked on him and played with his penis between my lips for a few more minutes before we headed back to the apartment.
On the way home, I held onto Jim's cock and stroked it really slowly. Anne gave directions. Jim fondled my leg and his cock started getting hard again. It was pretty late and Anne had him stop at the front door of the building next door. He reached one of his arms around me and hugged me and kissed me on the cheek and told us his phone number, which we promised to memorize.
Anne and I made our way back along the sidewalk to her building and went up to her apartment. Now my makeup was a mess, but there was no doubt that I still looked like a woman. My lipstick was completely gone, and Anne said that Jim's wife or girlfriend would probably notice that my lipstick was smeared all over Jim's long cock, and that Jim would probably be in a lot of trouble when he gets home. That night Anne made me sleep in wig, breast forms, one of her slinky body suits, and in thigh highs. I paid very careful attention to all of her instructions about disguising myself as a female both in and out of bed, and while sleeping and while awake.
The following day Anne drove me back to school. Over lunch, I finally got up the nerve to tell her that I really wanted to seduce her brother Rick. To my surprise Anne said, "When Rick sees you dressed as a woman, you are definitely not going to have any problem seducing Rick. The first time you do it, you need to do it the night of the pimp and prostitute party."