Tina and Rick - part 3 - Saturday Night's Alright

by Tina D

Last night, I had attended our dorm's "pimp and prostitute party" dressed as a female hooker.  I had previous experience cross-dressing, but my roommate's younger sister had taken me under her wing, and helped me look not only passable, but seductive.  She had given me the OK to seduce her rather ill-mannered older brother on the night of the party.  Now I wasn't sure if I had succeeded or failed.  Before falling asleep, Rick had summarily ordered me to give him a blowjob, and I had fully complied.  Following a huge orgasm in my mouth, Rick had promptly fallen asleep.  Waking up to find me snuggled up against him, still dressed in sexy lingerie, Rick had angrily and painfully thrown me out of bed and onto the floor the next morning.

Fearful of Rick's temper, I had called his sister Anne.  As I literally fled our dorm room, still dressed as Tina, Rick had angrily threatened me not to tell his sister anything about last night.  Anne quickly drove up and took me back to her hotel room, where she told me what I already knew.  Her brother had a terrible temper and it turns out that his temper had gotten him thrown out of college on previous occasions, and had kept him out of their family's trucking business.  She advised to spend the bulk of Saturday in her hotel room tub, and to get some sleep in one of the beds while she and her boyfriend, Phillip, explored the city a bit more.

Phillip brought me some complimentary breaksfast items from the hotel, and for the first time in 24 hours, I had something to eat... well, not counting the millions of Rick's sperm that I had gobbled down last night.  Once Anne and Phillip left, I also got out of Tina-mode for the first time in 24 hours.  The exception was my long pink fingernails that Anne had applied yesterday, no amount of soaking would coax them to come off in the tub.  While part of me was afraid to dress as Tina again, a bigger part made me had other ideas.

After a good 2 hour soak in the tub, I rubbed every inch of myself with excess baby oil, as Anne had told me to do following every bath or shower.  After just a few weeks, my skin was already smoother, softer, and even a bit shinier.  I brushed out my wig, and put it back on.  I picked out a nice bra and panties, slipped on a T-shirt, brushed on some very light makeup, and slipped into bed.  I was exhausted and had no idea how to fix things with Rick.  I wanted to cry but knew that Anne would make me feel better when she got back and so I closed my eyes and fell deeply asleep.

It was about 4:30 Saturday afternoon when Anne woke me up from a deep sleep.  She told me she had already spoken with her brother, and that he would meet us for supper at a restaurant just outside of town at around 7:30.  She also told me that she had already told Rick that I was going to appear as Tina, and he seemed fine with that.  Over the next couple of hours, as we got ready to go out for dinner, Anne asked a lot of questions, probing me about about my level of interest in living as a woman.  Phillip occasionally added some medical advice, for example, that if I made a transgender decision, I should act while I was young in order to achieve the best results.

While we were getting ready to go out for dinner, Anne strongly encouraged me to make one more attempt at seducing Rick, and so I dressed accordingly.  I was in tight Guess jeans, with pink high heel sandals.  Underneath a pink sweater, I was wearing my pink one-piece bathing suit, and pink thigh highs.  Before leaving for the restaurant, Anne had helped me pack up all of Tina's belongings in a large suitcase that Phillip loaded into the trunk of Anne's car.  We then headed for the restaurant where Anne and Phillip sat on one side of the booth, while I sat on the other side waiting for Rick.

Rick joined us about 30 minutes later, and slid into the seat beside me.  Anne and Phillip did a wonderful job of not hinting that they were aware that Rick had had carnal relations with my mouth the night before, or that he had acted violently towards me this morning.  Immediately after ordering dinner, Anne looked at Rick and said, "Tina has decided to take a year or two off school and undergo hormone therapy to to become a female."  This took me somewhat by surprise as I hadn't announced any such decision at the time.  But Anne having said it with such authority almost seemed to make it so.

Rick took two or three quiet sips from his beer and then said, "Well, hmmm.  That should be interesting to see."  Throughout the rest of dinner, Rick talked nicely to me.  In fact, he talked more nicely to me than I had heard him talk to any girl before.  As we finished up and Phillip paid the bill, he asked Rick to help him move my suitcase from the back of his car into the back of Rick's car.  Rick's response was "Why?"

Phillip responded, "Because you live with her, so you can just drive her home.  We're leaving the hotel early in the morning and heading for home."

"Oh, yeah, right, no problem," said Rick.

It was exciting to keep hearing everyone referring to me as "she," and "her."  In private, Anne told me I looked incredibly sexy, and to just take things slowly tonight, but that she was certain that her brother would come around before the night was through.  She told me to call her collect on Sunday night to let her know how things went.  With that, I walked over to Rick's car to get in the front seat.  Rick got into the driver's seat and told me, "I liked you better in a dress."

I responded with, "Well, these pants do come off."  I had no intention of being subtle.  Rick got quieter than usual, turned on the radio, and headed the car back towards town.

We parked on the street beside the side stairwell leading into the dorm, and Rick suggested we should head up the stairs.  I knew he didn't want anyone to recognize us in the elevator.  He did get my suitcase out of the trunk though, and carried it upstairs, without any prompting from me.  At least I would have something positive to report to Anne tomorrow night.  The instant we got into the room, Rick called one of his best high school buddies, and yakked with him on the phone for about 10 minutes.  I noted that during the conversation, Rick bragged that he had been out on a double date with his sister; which was interesting to hear.  Rick was watching me empty my new wardrobe from my suitcase into a dresser while he chatted on the phone.  The instant Rick hung up the phone, he asked me if I wanted to watch a movie with him.

Rick popped open the TV guide and searched for a movie he would enjoy.  I poured a beer for Rick, and got myself a diet soda.  We sat down beside each other part way into "Scream."  About 10 minutes later, I had my feet curled up on the couch and I could see Rick eyeing my legs and heels.  "I thought you said those pants could come off," said Rick.  I carefully unbuckled the ankle straps on my shoes, and then slid my jeans off as sexily as possible, exposing my legs clad in pink thigh highs.  I snuggled back up into the corner of the couch, pulling my legs up in front of me so Rick could look at them easily if he wanted to.  I knew that Rick was a "leg man," and he took a good look.  Another 10 minutes passed by and Rick said, "What exactly is under that sweater, anyway?"

I expected this to be a "make or break" point with Rick.  A lot of time and effort had gone into using adhesive to carefully secure my silicone breasts into place, but even more time had gone into shopping for a bathing suit that would perfectly and completely cover the breast forms.  Anne and I had found such a bathing suit, and while it completely contained my breasts, it rode high up on my hips to give me an extra leggy appearance, and aside form some thin straps that crossed in the middle of my tanned back, the back of the bathing suit consisted of a shirred stretch panty that helped to visibly round and shape my butt.

Once the sweater came off, Rick asked me to strap my heels back on and walk around the room a time or two to let him have a better look.  The extra time spent finding the perfect bathing suit had paid off.  I didn't quite make it once around the room when Rick was up and off the couch and wrapped me in his arms from behind.  He was holding me tightly and squeezing my breasts as if they were real.  He ordered me to get on his bed while while he got undressed.  I grabbed a tube of lubricant out of my pocket book, and some extra pillows off of my bed and spread out on my back on Rick's bed.

I didn't realize it at the moment, but I was about to find out that Rick has possibly the strongest libido of any living human.  For the next 20 hours, Rick was either having explosive sex with me, or sleeping between orgasms, and I apologize in advance for the very explicit description of the events described below, but this was an absolutely momentous occasion for me, and led to a huge turn in the direction of both of our lives.  If you are easily offended, here is a good jumping off place, skip to the last paragraph!

Rick lay on top of me and kissed my neck a few times, and I thought we might be in for a fairly romantic evening, but evidently Rick had some sexual tension to work off first.  He slid me part way down the bed, still on my back, spun around over top of me, so he was facing my feet, and then, while on all fours, he jammed his cock into my mouth and started fucking me.

I say that Rick was fucking my mouth because he was anything but gentle.  He was on all fours and was pounding his rod into my mouth like it was a seasoned pussy.  Just like the last time his cock had been in my mouth, he started to become impossibly hard again and his thickness was seriously stretching my mouth.  Unlike the last time, though, he was being awfully quiet.  I kept thinking to myself, I have to make him cum at least once before he considers sticking this huge thick thing into me, otherwise he is going to tear me to pieces.

But that was when I realized that Rick was not going to let me make him cum in my mouth.  His plan seemed to be to use my mouth to get super hard before spearing me in the ass.  Every time he would start to enjoy my mouth too much, and his pre-cum would start leaking into me, he would pull out.  He would wait about 5 or 10 seconds, and then reach back and quickly and forcefully jam his cock back into my mouth and pound away for another minute or two.  He kept this up for about 15 minutes during which I unsuccessfully did absolutely everything in my power to make him cum; I licked him quickly and slowly, I sucked him forcefully and gently, and I repeatedly deepthroated him, although not by choice.  But he would not let me make him cum.

At this point, he pulled out of my mouth, and spun around over top of me.  He flipped me onto my stomach and shoved a pillow under my hips.  I was 100% certain now that he was going to fuck me in the ass, and I started pleading with him to let me make him cum with my mouth first, assuming that his cock would soften up a bit after an orgasm.  The only thing I was sure of now was that Rick was horny beyond imagination, his cock was hard beyond belief, and he was not listening to anything I said.  He was feeling up my legs and ass and I was madly squeezing KY onto my hand and swiping it into my ass as he was spreading my legs apart.  The instant that Rick saw that he could slide the bottom of my bathing suit over to the side, giving him a clear shot at my ass, he was on top of me and pushing his cock into me.  I was begging him, "Slow baby, please, slow, slow, slow, gently baby, please, gently.  Baby, let's get a condom first."

But it was too late to think about condoms.  His cock head entered me with a physical pop that I could feel from my head to my toes, and oh how it hurt.  His head was fully engorged with blood, and so I assumed the worst was over, but once again, I was wrong.  Evidently, Rick loved the feeling of sliding his cock head into my ass, and so he promptly began pulling it out and popping it back into me, over and over.  I was biting a pillow in an attempt not to scream and I know Rick could feel my whole body shudder every time he shoved his cock head back into me.  I was already hoping I would simply survive the ordeal so I could call Anne the next night.  To make matters worse, my ass was squeezing hard on Rick's cock in an attempt to keep him out, and while I am sure that the added tightness was adding to Rick's pleasure, it was certainly making matters worse for me.

"Oh, baby, it's too hard, please baby get it out of me, it's just too hard, I can't take it, please pull it out."  He pulled out every time I begged him to, waited a second or two, and then shoved himself right back into me.  He finally decided to snuggle closer and fuck me in earnest.  Evidently I hadn't fully appreciated how thick Rick was midway along his cock shaft, but I soon did.

Rick was leaning way over me now, and pulling himself nearly all the way out, and then quickly and forcefully shoving himself all the way back in to me.  My ass was squeezing tighter and tighter on him as I tried to prevent him from pushing into me, but I quickly learned that stopping a cock from sliding into a lubricated ass is totally impossible.  The harder I squeezed trying to get him out, the more excited he got and the harder he pumped.  And the harder he pumped, the more he jabbered.  "Oh, you sweet little fuckdoll, I am going to fill you so full of cum that you are going to explode.  I am going to get you so pregnant that your belly and tits are going to swell up like beachballs."  Yes, you heard me right, he said he was going to get me pregnant.  "My cum is going to be leaking out of your pussy for days.  Oh you tight sweet assed little fuckdoll."  Yes, you heard me right again, my pussy.  And the pounding got harder and harder and faster and faster.

My ass muscles had already completely surrendered to Rick's continued pounding, because they had no more energy to fight his jack-hammer like cock.  Rick was now free to totally have his way with me, and he knew it.  He was telling me over and over how much I loved the feel of his cock slamming deeply into my body, and how much I wanted his cum in me.  I was just lying totally limp underneath him, moaning loudly, still hoping to survive the beating I was taking from the huge cock impaling me, and absolutely loving each and every moment of it.

Rick suddenly dropped his whole body weight flat onto me and I was so grateful because I knew he must be close to cumming, and because he could not pull his cock back as far each time he thrust into me.  He was still in me deep, but things were less painful as he was no longer pulling the thick center of his shaft out with every thrust.  Now I just had to keep breathing with his full weight on me until he shot his load into me.  With superhuman effort I started to squeeze on him again, hoping desperately that I could make him cum faster.

The instant I started squeezing, he quit jabbering and it was his turn to start moaning.  So I squeezed harder and harder.  I squeezed his cock for all I was worth.  I squeezed on him deep inside my ass, I squeezed on him with my entrance hole, and I squeezed on him with my ass cheeks.  Every time he pulled back a little, I would relax, but every time he pushed, I used every muscle I had to squeeze every inch along the length of his entire cock so he would feel nothing but super intense tightness surrounding his thick cock.  Rick was absolutely uncontrollable at this point.  I hadn't imagined that it was possible for human hips to move as fast as he was pounding in and out of me, it was like being fucked by a powerful high speed machine.

When Rick finally came, I thought he was going to break me in half.  He grabbed me with his arms around my chest, and his hips thrust into me so hard that it felt like he was trying to fuck me right through the mattress.  His entire body stiffened, and his cock started to pulse, and one after another I felt every shot of his hot cum being delivered deeply and forcefully into my body.  Rick held nothing back from me, he let me have the full brunt of his most powerful orgasm.  With every pulse of his cock, he got bigger and pushed deeper and harder, and again I was begging him to pull back out of me.

But even after he finally stopped spurting cum inside of me, he didn't offer to pull his cock out of my ass.  Instead, he waited just a few seconds, and then began roughly pumping that monster inside me again.  As he did, he kept repeating things like, "You liked that didn't you bitch, you want it again, don't you bitch, that was the best you ever had, wasn't it bitch?"  Within a few minutes, I could feel that he was getting harder again and I was just determined to do my best to hang on through the next round.  But suddenly, Rick sat up and jerked his cock out of me.

Now he lifted me and flipped me over onto my back again and I could see his huge cock standing up in front of me.  I literally gasped at the sheer sight of his cock looming so large and so close to my ass.  Looking at the size of his cock, I knew there was no way I could survive having that huge monster force its way back into me, absolutely no way, and I said, "Please baby, let me suck you, I'll suck you all you want, I'll suck you all night, just please don't try to put that thing back into me."  Rick completely ignored me as he shoved a pillow back under my hips and grabbed my ankles and lifted my legs, high heels, nylons and all, straight up into the air.

Rick didn't have to look hard to find his intended target beneath the crotch of my bathing suit; there was a huge cum and lube stain leaking out of me.  "Baby, please don't, please let me suck you."  But there was absolutely no stopping Rick at this moment.  As he slid his big rod back into my ass, he locked his hands like vices around my ankles.  I held my eyes tightly shut as I tried not to faint, and he resumed his relentless pounding in and out of me, and I heard him start chanting his monolog again, in perfect rhythm to the brutal workout he was giving me with his cock.

"Oh, you sexy hot legged little fuckdoll, you have such gorgeous fuckable legs, and such a gorgeous fuckable mouth, I have so much cum that I am going to shoot up into your body, my cum is going to be leaking out of you for days, my cum is going to own every inch of your body, you are so built for sex, you sweet hot little fuckdoll, you incredibly hot little cum receptable, you are so incredibly totally fuckable, I am going to breed you you little slutdoll."  And on and on, non-stop, he continued to chant while he relentlessly fucked me into complete and total submission with that restless, huge, massive, hard, thick cock, in and out, in and out, in and out.

Finally, Rick rolled me over onto my side, lifting one of my knees against my breasts, while he squatted over my other leg.  Effectively, he had my ass stretched wide open around his massive cock, and, about to blow another huge load in me, he said, "Get ready fuckdoll, baby, you are about to get cummed so hard you aren't going to believe it."

I cannot even begin to describe how totally helpless I was as I lay there with Rick just pounding and pounding and pounding his big rod into my ass.  When he came this time, rather than begging him to pull out, I was begging him to shoot into me, desperate for him to stop pounding me for just one or two minutes.  "Please baby, please cum in me, please, please, please, please, please cum in me baby, please cum deep inside me, please give me every drop of your cum baby."  Rick's hips thrust against me forcefully, and his rod pushed further into me than before, and swelled up even bigger and pulsed even harder than before.  As he came inside me, my ass was helplessly locked onto his over-sized cock.  Every time he pulled back, his cock was literally lifting my ass off the bed.

When he was done cumming inside me, he still didn't pull out of me and I thought to myself, there can't be more.  The problem was that his cock was just too long, and we were still so close together, that his now empty cock simply did not want to pull out of me.  Rick grabbed onto me and rolled us both over onto our sides, his cock still locked deeply inside my ass.  We fell asleep joined together by his cock on Saturday night.  I was woken up twice more on Saturday night as Rick gave repeat performances, pumping me gently this time, and cumming in me from behind as we lay side by side.  Each time he came in me, he said, "My sperm are everywhere inside your body now, baby."

And there was no doubt about what he said.  Rick had cum in me four times already, and each time had blasted a huge load deep inside me.  While I could feel cum leaking down my legs and onto my nylons, I knew that the vast majority of his sperm were still swimming around far up inside my body where they had been so forcefully ejaculated.  I had been completely physically overwhelmed by Rick's penis and lay helplessly exhausted in his arms.  I fell asleep, thrilled at the thought of millions upon millions of his sperm swimming around deep inside me.

Sunday morning was quite a different awakening from Saturday morning, when I had been thrown out of bed onto the floor.  On Sunday morning, I was awakened by Rick shoving my head into his crotch for an early morning blowjob.  Once his penis was good and stiff, he asked to see what other goodies I had to wear, and he picked out a black body suit, black nylons, and my black cum-fuck-me-pumps.  After a quick trip to the washroom, he had me squatting over him on my high heels as he watched my ass slide up and down on his huge prick.  After another big orgasm inside me, his fifth since we had started last night, he wrapped his arms around me and told me not to get out of the bed, and he fell back asleep.

When he woke around noon, he told me to get on all fours and he promptly fucked me one more time, again devastatingly hard, this time doggystyle, and flooded me with another unbelievable amount of cum.  I crept out of bed when Anne called at about 4 pm to see how we were doing, and as I stood by the desk talking to her on the phone, Rick mustered enough energy to get out of bed, bend me over the desk, and fuck me one more time.  As I tried to blurt out a few words to Anne, he literally fucked me so hard that I dropped the phone out of my hand.  I have no idea how long Anne listened, but Rick gave my ass a full five minute super hard workout while I lay helplessly sprawled out over the desk.  I was sure that Anne was still on the phone and was listening to the whole thing, with Rick grunting, me moaning, and Rick letting go with one last huge orgasm deep up inside me.

After seven orgasms inside me in less than 20 hours, Rick was finally sexually exhausted, and he became interested in eating and drinking beer once more.  Other than a quick trip to the drugstore the following morning, I spent all Monday in bed trying to recover from everything Rick had done to me.  By Tuesday, cum was still leaking out of me, and I was just barely able to sit down comfortably.

With just five weeks of the semester remaining, Anne visited me twice each week, and she was a whirlwind of activity.  She got Rick to drop out of school and return to work with their father; Rick's scholastic record was a lost cause.  She made arrangements for me to see a doctor and begin hormone therapy.  She made arrangements for Rick and I to move into a cute little bungalow her father owned just 20 minutes drive from their local trucking yard.  She had our new little house cleaned up and ordered us a few new pieces of furniture.  She made arrangements with their father to let us live rent free while Rick received a reasonable monthly living allowance.  And she found me a decent paying job at a nearby video store.

I managed to complete my classes, despite visits from Rick every weekend, during which it was necessary to be dressed as Tina before Rick arrived on Friday nights, and during which it was virtually impossible to study unless Rick fell asleep.  I was also experiencing mood swings with hormone therapy, and that didn't help.

Anne found a doctor who claimed to set really high goals for his patients.  He was glad to see that I was already "passable plus" when dressed, and told me that, if I followed his plan, our goal would be "passable plus in a string bikini within a 2-3 year time frame."  The doctor told me that I produced male hormones, but not as much as most males.  But my problem wasn't low male hormones, it was that I didn't respond well to male hormones.  He said patients like me generally responded extremely well to female hormones, and I started therapy that day, with samples he had from a drug company.

After final exams, Anne showed up to help me pack and to drive me home to Rick.  Rick and I were about to "shack up!"