Tina & Rick - Part 2 - The "Pimp & Prostitute" Party

by Tina D

Our all-male dorm was planning a "pimp and prostitute" party.  I had already told my much older roommate, Rick, that I was going to attend dressed as a female hooker.  A few weeks before the party, Rick's younger sister and I had quickly became friends.  She spent three days and two nights teaching me to better dress the part of a woman, including helping me to buy some goodies I would need to wear.  She had taken me out for a "practice" walk downtown at night, and a total stranger ended up paying me to give him a handjob in the front seat of his car.  At the end of my visit, I admitted to Rick's sister that I fantasized about seducing her brother.  Anne gave me the go ahead, telling me, "You need to do it on the night of the pimp and prostitute party."

The day before the party I was happy to get a call from Anne saying that she and her medical resident boyfriend, Phillip, were in town and that they were planning to stay over and attend the party the next night.  The next words out of her mouth were, "How about another little shopping trip tomorrow morning?  I'll pick you up at the side door to the dorm at 9 am."  What Anne didn't tell me was that she was actually planning on going shopping with my new alter ego, Tina, whom Anne had helped create.

Anne drove up at precisely 9 am and promptly sent me back up to the room to get everything I needed to transform into Tina.  "Bring everything, clothes, lingerie, makeup, everything," she said.  Ten minutes later we were in her hotel room where Phillip was still in bed and catching up on the news.  After brief introductions, Anne had me in the bathroom and started working on me.  Anne had lots of extra clothes with her, and by 11 am, I was in light makeup, tight fitting capri jeans and sandals with kitten heels.  A loose fleece pullover played down the size of the extra large breast forms we had purchased for me a few weeks ago.  I felt like a pert and pretty brunette soccer mom, and we were ready for the stores.

When we finally walked out of the bathroom, Phillip's first words were, "Mmmm, I definitely like you better this way."  Maybe he knew I needed an ego boost before my first fully dressed outing in broad daylight.  I learned three really important things from Anne that afternoon.  First, learn how to be more like a woman from a woman.  Second, if you are passable, don't be afraid to shop with your own credit cards, because when store clerks see a male's name on a credit card, they assume that your boyfriend, husband or father is paying your bills.  Third, relax and act natural, and forget that you are playing a part.  If you think too much about trying to act female, you get nervous.  If you want to look at bras, and you are relaxed, you will probably just look like another woman looking at bras, and no one will pay any attention to you.

In addition to bras and panties, Anne and I bought items to start my new wardrobe, including a couple of skirts, dresses, blouses and sweaters.  We picked out my first bathing suit, a dark pink one-piece that covered my whole front side, almost to the collarbone, but covered almost none of my backside.  We found a pair of outrageously sexy black high heels (those classic "cum fuck me pumps"), and Anne chose some really sexy, and very expensive, black and nude color "foundation garments" for me.  As I paid for the first batch, the only question the sales clerk asked was, "Did you find everything you were looking for?"

We spent the better part of the afternoon in a big mall, mostly filled with women shoppers and female clerks, and I didn't get even a single funny look.  Just one more of the girls out shopping on Friday afternoon.  As usual, my father paid all my credit card bills, and I never heard a single complaint from him; later I learned that he simply paid the bills without looking at the itemized statements he was receiving.

We headed to the hotel to relax, eat, and get cleaned up and dressed for the party.  At the hotel, Phillip started digging through our bags, and Anne immediately sent him out to get pizza.  I had nothing but exciting thoughts running through my head while Anne and I sat on the beds talking.  I was relaxing as a woman, and hadn't even thinking about getting out of Tina mode.  I had a wonderful female friend helping me carry out my plan to seduce her brother.  I was excited about getting really dolled up for a party.  And finally, I couldn't stop imagining how wonderful it would feel to have Rick's cock slide into me.  We were roommates, I found him attractive, and I had had plenty of opportunity to see the size of his package.  Rick had his bad points, including being rude most of the time, but he was big all over.

Anne finally got a hold of Rick on the telephone, and told him that we would meet him in our dorm room around 9:00 pm.  The parties generally didn't get really outrageous until after 10 pm.  By 11 pm it was pretty much anything goes.  After pizza (I couldn't make myself eat anything), we started getting ready for the party, and Phillip joked about how long women take in the bathroom.  This time when we came out of the bathroom, Phillip's response was, "Holy shit, you two look hot!"  When we left the hotel room around 9:30, I felt completely female.  Our hair and makeup were perfect, but Anne and I were both a little overdone to give us the hooker look.  Both in short, tight slinky black dresses with black fishnet tights and sexy high heels strapped around our ankles.  I now had long pink fingernails.  Anne had given me her personal guarantee that I was going to have a lot of trouble getting my wig and nails off the next day, and so I needed to forget that I was wearing them tonight.

Underneath my dress I was wearing crotchless black high cut panties and a skin hugging one-piece body briefer that snapped closed at the crotch.  This will sound horrible, but I had already squirted some vaseline up into my rear end, in the hopes that things would be a bit more spontaneous if everything went as I was hoping with Rick tonight.  I thought my chances of seducing Rick were really good, after all, I looked good, and he would have to stay overnight in the same room with me no matter what happened.  Just before we left, Anne gave me a small black cloth handbag with a long shoulder strap.  She told me to check out the contents.  Lipstick, lip gloss, a small bottle of lube, and half a dozen condoms.

I couldn't believe how smoothly things went.  When we walked out of the hotel, we both received appreciative glances from men hanging around outside the door to the hotel bar.  I didn't have even the slightest doubt that, while there were going to be some really incredibly sexy looking girls at the party, I was definitely going to look better than the average girl there, and there was no way any straight guy could look at me (without knowing) and not find me at least somewhat attractive.  Sitting in the front seat of Phillips car made me think of the last time I got in the front seat of a guy's car dressed like this, and that guy had shot cum all over me after paying me to give him a handjob.  He had actually come within an inch of getting a blowjob from me, but he came before I could muster up the courage to give my first blowjob.  And I was feeling confident knowing I looked better than I did that night.

Needless to say, I felt totally sexy as we swung our sexy looking legs into and out of the car and strutted around in our extra high heels.  We walked into the dorm nearly an hour late and took the elevator upstairs.  As we walked down the hall to our room, Anne said she didn't think that the guys walking past us in the halls recognized me.  A few of them gave Anne and I both the once over, but no one called me by name or appeared to know me.  Anne knocked on our room door rather than letting me unlock it, and to my surprise, Rick was actually there waiting for us rather than having already headed down to the party to start drinking.  Even more surprising was the usually rude Rick's response to me.  He looked at me, let his head snap back a little, and said, "Wow, you actually look pretty good as a broad."  Having said that, Rick who was in his usual clothes, no costume whatever, was ready to go downstairs and start drinking.

Rick took off downstairs without us, while Phillip asked some casual questions about the room, and the college.  Anne and I then went off to use the bathroom together, the women's bathroom, just as we had done a couple of times earlier in the day while shopping.  When we got back to the room, we collected Phillip and started for the elevator.  Phillip grabbed both of us by the arm and told us again that we were both really hot looking.  I was watching Anne start to turn it on showing off her legs as we walked down the hall, and I tried to do the same.  I definitely didn't have Anne's practiced natural sexiness in heels, but I was definitely having an effect on some of the guys who were ogling us, heels, legs, breasts and all, and their eyes trailed us as we walked along the ground floor hall to the party lounge.

The party was really loud, as usual, and very dark until your eyes made the adjustment.  Phillip was already back from the cash bar and handed us each a beer as we leaned up against the wall.  All of the chairs were already occupied by the guys who were known pretty much for sitting and drinking throughout the duration of the parties.  One of the chairs was occupied by Rick.  Now, I was sneaking peaks at him.  Rick appeared oblivious to the fact that we were there, and Anne yelled in my ear, "Ignore him."  Anne and Phillip were real troopers; they stuck by my side for the first half hour that we were there.

And then something kind of exciting happened, a guy who literally towered over me, and that I had not seen before, bent his head close to my ear and asked if I would dance with him.  This was a great opportunity for me, because I had great rhythm anyway, and growing up in a house with two sisters, I had secretly practiced every sexy dance move they knew.  I just sort of let go, and made it through two fast dances with this guy before the DJ put on a slow one.  I must have sent all the right signals because as soon as the slow dance started, this guy reached around behind me, put both his hands directly on my ass, and pulled me against him.  He had thin dress pants on, and as we danced, I could feel his growing erection pressing against my stomach.  In fact, as the music played along, he was doing everything he could to make sure I knew he had an erection, and I could feel him pressing it harder against me as he held me against him.

I was absolutely, incredibly turned on by this guy pressing his penis against me and squeezing my ass as we danced.  I was already thinking that if something didn't happen with Rick pretty soon, then this guy would definitely be getting a blowjob tonight, at the very least.  I still had no idea who this guy was, but he told me he had to go to the can and asked if I would be sure to hang around and dance with him when the DJ played the last slow number tonight.  "Yes," I said as he headed off to the bathroom.  I quickly looked around to find Anne and Phillip, who had also been slow dancing.

As we made it back to the wall, Anne yelled in my ear, "It looks like you have a new friend.  And what the hell was that all about, where on earth did you learn to dance like that?"

"I was watching the way he was feeling up your ass while you were dancing and I'm going to wager fifty bucks that he is going to ask you to go home with him tonight," Phillip added.

Just then, Rick shows up and joins in the conversation.  "This party totally sucks.  Why don't we head back to the room and have a few beers?"

While Phillip and Rick discussed the merits of going back to the room, Anne said to me, "Someone else was watching that guy feel up your ass.  Rick isn't going to go back upstairs unless you do."

"You have to be kidding!"  I stepped over to Rick and said, "Well, why don't we stay and listen to the next couple of songs, and then head upstairs."

"Sounds good to me," said Rick.  About a minute later he grabbed my arm and said, "What the hell, let's dance."

Rick and I danced through the next fast song, and at the pause in the music I said, "Why don't we go upstairs now?"

Rick was looking directly in my eyes when he said, "OK, we're out of here."  And I don't know if he was conscious of it or not, but he grabbed my hand and held it while we walked back to where Anne and Phillip were standing.

Anne and I headed out the door and down the hall with Rick and Phillip trailing along behind us.  I was hoping that Rick was at least appreciating the way I looked from behind, because while I was excited about looking the part, every moment I had spent dressing had been with the intent of getting Rick aroused.  Rick was actually being pretty polite, maybe because Phillip and Anne were there.  He stepped up to hold the elevator door open and said, "Ladies first," with absolutely no cynicism in his voice.  When we got back to the room, Rick put on some quiet music and we all sat down to chat.  Anne and Phillip sat on one of the beds, and Rick and I sat on the couch.  I sat down and crossed my legs.  Rick handed me a beer and sat pretty close to me, looking straight at me and saying "Man, I can't get over how good you actually look.  Now if I could only find a girl who looked like you I'd have it made."

We listened to more music and Anne made us all talk for at least another hour.  Rick drank a few beers and I didn't even finish half of my first one.  Phillip was very obviously totally horny and wanting to get Anne back to their hotel room.  Anne was teasing the shit out of him with her hand close to the bulge in his pants.  Rick was definitely sneaking peaks at me, and not just at my legs and boobs, but at my face as well.  I couldn't see any bulge in Rick's pants, but there was absolutely no doubt now that he he was checking me out.  Finally, Anne asked if the two of us would join her and Phillip for Chinese food the next night, at a restaurant they had found just outside of town.  "As long as I don't have to pay," answered Rick.

Before Anne and Phillip left, Anne and I took a trip to the bathroom.  On the way to the bathroom, Anne very casually stated, "Rick definitely wants to have sex with you."  As they left, Anne hugged me and whispered, "Have fun baby!  And don't forget to make him wear condoms!"

Rick was still sitting on the couch sipping on his beer.  I had no idea what to expect when I turned around and walked back into the room.  Rick got up and turned on the television and asked me to come and sit beside him.  The last thing on my mind was watching television, and I knew I was going to have to turn the heat up a bit.  Rick found an old re-run of one of his favorite sitcoms.  I got up and headed for the fridge saying that my beer was too warm and I needed a cold one.  Rick told me to get him one too.  As I dug around in the fridge, I bent way over, still in my cum-fuck-me heels, and struck my sexiest pose.  With my dress riding up over my fishnet nylons, and my ass nearly straight up in the air and pointed in Rick's general direction, I twisted around to ask Rick what kind of beer he wanted.  He was looking right at my ass and I am absolutely sure I caught him rubbing his crotch.  He quickly pulled his hand away and told me that any kind of beer was fine.

When I sat back down beside him, I sat right against him, so that my thigh was touching his leg.  Rick immediately started talking again about how much he wished he could meet a girl who looked like I did tonight.  "Fuck, your legs are so totally hot looking.  Why can't I find someone with legs like that, man they are hot.  And your ass, tits, everything, you just look totally hot.  I would give anything to find someone who looks anything like you look right now.  Have you looked at yourself in the mirror, you look really totally fucking hot."

And this is when I asked him, "Would you like to fuck me?"  I had mistakenly assumed that he would to jump at the chance, throw me on all fours on the bed, pull my ass up in the air, grab me by the ankles, and start banging me into submission, but that didn't happen.

"Oh, shit no.  Fuck.  I just want to meet someone who looks like that.  I mean, fuck a girl who looks like that."

"It's just a body, Rick, it's not that different from a girl's body.  You can fuck me if you want to."

Rick got really quiet for a minute and put his hand on my thigh and started rubbing.  As far as I was concerned this was my signal to reciprocate so I reached around, unbuckled his belt, pulled out his cock, and started giving him a handjob.  The first time I did this to a guy, he literally exploded in my hands, but Rick was only getting semi-hard.  I figured he had either had too much to drink or he was just not all that interested.  Before I had a chance to think about the possibility of trying to use my mouth to get him hard, Rick got up and walked over to his bed.  He pulled off his pants, and sat down on the bed.  I thought he was going to go to sleep.  But then, sitting on the edge of the bed, with his legs spread apart, he started pointing at his dick and literally ordered me, "Get over here and suck this thing off, you little fuckdoll!"

I definitely didn't hesitate now.  I walked over and got down on my knees between his legs, and sucked his rod into my mouth.  Evidently there was no beer problem, and there was no problem with interest level.  Maybe he had just gotten tired of being polite for a couple of hours.  His cock was growing harder by the second inside my mouth.  I knew his cock was big, but I had never seen him with an erection before.  He was enormous and I knew I was going to have a sore jaw tomorrow.  I started to worry about how on earth I was going to get this huge thing in my ass.

But for now, I was totally intent on loving his cock with my lips, tongue, mouth and throat, and giving him the blowjob of a lifetime.  I was sliding my mouth onto and off of him, trying to deepthroat him, and making a lot of slurpy sucking sounds every time I pulled him out of my mouth.  He was really starting to jabber now as I kept up the sucking action on his rod and massaged his balls.  "Oh, yeah baby, suck me, suck my cock, fuck, let me cum in your mouth, fuck me with your mouth baby, oh yeah, fuck me with that gorgeous fuckable pouty mouth of yours, you hot little fuckdoll."

I could feel his balls pulsing in my hands and I had already swallowed several streams of the pre-cum that was leaking from the end of his cock into the back of my mouth.  I knew he was close to cumming when he pulled my head back off the end of his cock.  He laid as far back on the bed as possible, right against the wall, and told me to turn around and get on the bed with him.  While I continued to suck away on his impossibly hard cock, he was alternately holding onto my heels, clenching onto my ankles so tightly that I felt like I was in cuffs, or sliding his hands up into my dress and fondling my legs and ass.  His big rod was leaking more and more pre-cum into my mouth and I started to wonder if he was actually cumming.  But I got my answer after a few more minutes of continued sucking action.  This position was great because I could slide my head down along the shaft of his cock and actually feel his cock head bumping against the very back of my mouth.  I would slide my mouth as far down his shaft as I could and suck on him hard, and then slide back up and get a much needed breath.

Rick was absolutely beside himself at this point, repeatedly telling me to keep fucking him with my hot, tight little mouth.  "Oh you sweet hot little baby fuck doll, oh suck me, fuck me with your hot little mouth baby, oh baby I am going to shoot so hard into your hot fucking little mouth, I am going to fill you wish so much cum you huge titted little fuckdoll.  Swallow every drop you hot little fuckdoll."  And as I was sliding my lips, tongue, mouth, and throat up and down on his rock hard cock as fast as I could, the spurts of cum started.  It was the most incredible feeling as I clung onto his cock with every part of my mouth.  Huge, thick squirts of cum, at least 10 hard squirts as I kept alternately sucking and trying to breathe.  It felt like someone had stuck a big squirt gun in my mouth and was shooting jets of hot water in my mouth.

And the cum doesn't just shoot down your throat like you might expect, it shoots everywhere in your mouth, spurting against your tongue, or the roof of your mouth, or your teeth, or once in a while into your throat, and then the cum just runs absolutely everywhere.  It runs under your tongue, through your teeth, into your cheeks, it is an amazing feeling.  Rick was finally starting to relax but his hips were still a few inches off the bed and my mouth was still wrapped around and tightly sucking on his cock when I realized that, while Rick was trying to blow his giant cumload through the back of my head, I had completely forgotten to swallow.  Rick was obviously amazed at what he had just experienced and he was watching me intently as I continued to suck on him and began to swallow the huge load he had just deposited in my mouth.

I kept sliding up and down on his cock and swallowing his ultra large volume, ultra thick load bit by bit.  Rick obviously had not cum for a long, long time.  I was definitely swallowing a maximum two ball cumload.  It was very thick, it was hot, and it coated my mouth.  I wondered how many millions of sperm I still had swimming around in my mouth, and how many millions I was swallowing with each gulp.  After several more seconds, I finally got the whole creamy load down my throat, and Rick, who was still propped up and watching the continued sucking action on his cock,  asked, "Baby, did you just swallow every drop of my cum?"

I was sucking him very gently and slowly now, but stopped sucking just long enough to say, "Yes," and then Rick again pulled my head off of his cock with a big slurp.  Now he literally physically turned my body around so I was lying directly in front of him with my back against him.  He slid one of his hands up under my dress and started fondling my ass, squeezing it pretty hard, and then pulled me back against him like I was a little paperweight.  He had his arms around me holding me tightly and jammed his hips even tighter up against my rear end and he started humping against my ass with his naked cock, hard.  I was so incredibly excited at this point that I thought I was going to burst out of my skin.  While Rick kept humping against me, I reached between my legs and started to undo the snaps in the crotch of my snug fitting one piece body suit.  Once the snaps were undone, Rick's cock would have a clear path leading straight into my tight little virgin ass.  My high heels, nylons, and crotchless panties were all inviting him to spear me.

As I reached back to guide his massive cock into me, I knew this was going to be more than a little bit painful.  I had now seen Rick's cock in full glory and I knew that all the vaseline in the world would not make this experience painless, but I thanked myself for at least having tried to prepare my ass for Rick's jumbo sized cock by lubing in and around my opening before leaving the hotel.  Anne was going to be mad at me, though; from the minute Rick's cock got hard in my mouth, I was in dreamland, and had completely forgotten about the condoms she put in my new handbag.  I was holding his cock in my hand, and was mentally prepared for him to enter me, and I certainly wasn't expecting Rick to be the gentle type.  Then I heard this rumbling sound.  Rick and his huge, hard cock had fallen asleep and started snoring.  His cock was still very big around, but it was already getting soft in my hand.  I turned around and kissed and sucked on his penis for at least 30 minutes, determined to find out if it was possible to make him hard, and even to cum while he was asleep.

His sleeping cock alternately got semi-hard and then soft in my mouth.  I didn't care, I just wanted to kiss and suck on it for a little while longer.  Eventually, I turned back around in the bed and snuggled back close up against him and fell asleep.  I only took off my dress and high heels, thinking that Rick would enjoy waking up with his cock already snugly pressed up against the shapely tight ass of his "fuckdoll," who would be more than ready for him to penetrate her ass with his cock, in her very sexy black body suit and fish net thigh highs.  I went to sleep against the warmth of Rick's body, imagining that we would spend all day Saturday in bed, with Rick literally using his oversized cock to fuck me to pieces.

The morning brought a different reality.  I was already lying awake when Rick started to wake up in the morning.  It was already light out, and I could feel Rick's hands on my back.  I was wondering if he was trying to figure out the best way to slip his rod into me, when all of a sudden he shouted, "Fuck!"  And then I felt him shove both his hands hard into the middle of my back and he literally tossed me out of the bed and onto the floor.  He jumped out of bed and grabbed a robe, soap and shampoo and headed for the bathroom.  He was acting very angry and so I remained on the floor, and did my best to stay out of his way.  On the way out the door, he uttered another, "Fuck," and he was gone.

This couldn't be good.  I grabbed the phone and called Anne.  Thank goodness she was already awake.  She explained to me what I already knew, that Rick has a very bad temper, and she promised me she would meet me downstairs in five minutes.  Quite frankly, I didn't even think of trying to get out of my Tina things.  I took a quick glance in the mirror, and convinced that I still looked like a Tina, quickly slipped back into the dress and heels I had worn last night.  My hair and makeup were a mess but I headed down the hall and past the bathrooms towards the elevator.  And out of the bathroom here came Rick.  And he asks me in an angry voice, "Hey, I thought we were going to dinner with my sister tonight, where the hell do you think you're going?"

"I'm going downstairs to meet your sister right now."

"Just keep your fucking mouth shut about last night," said Rick as he walked angrily towards me in the hallway.  I quickly ducked through the door to the stairwell, and found out that it is possible to run downstairs in spiked heels.