Paradiso Ch. 08

Day 2 Continued

My head was buzzing with alcohol and anticipation as we walked back to our room; Sara, Jessie and I. I intentionally let myself fall behind a couple of steps so I could watch their asses sway from side to side as they walked. It was a lovely sight; Sara's toned body with its fair skin and dark hair flowing down her back and Jessie's curvaceous figure, tall, tanned and blonde, with the great red-brown tattoo sprawling across her back. The thing that had my stomach doing flip flops was what I couldn't see. Between Jessie's legs hung a long, thick, beefy cock. Jessie was a transsexual and when we got back to our room Jessie was going to make good on her promise to shove that monster piece of meat up my ass.

It certainly wouldn't be the first time I had something in my ass. Sara had introduced me to ass-play early in our relationship and I had come to love the pleasurable sensations she had given me with all manner of dildos, vibrators and strap-ons. However this time was different because Jessie's cock was considerably bigger than anything Sara has ever put inside me, and also because Jessie's huge dick was real.

Sara and Jessie talked about all the sex they had since arriving. Sara recounted the story of our meeting with Lauren, the gorgeous black vixen we had met on our first night, and David and Maggie, the mature British couple who gave us some lessons in twisted pillow talk. Jessie talked about all the men and women on whom she had used her impressive piece of girl meat. Apparently she prided herself on taking straight men's anal cherries. She just came right out and said so, knowing I'd hear. She wanted me to know that I was a conquest, a notch on her belt. It was all a part of her dominant nature and I resolved to go with it.

We soon arrived back at our room and Jessie turned to us.

"I'm taking a shower." She announced. "We should get nice and clean."

"Sounds good." Sara agreed. Jessie then took us both by the hand and led us to the shower. She started two of the shower heads and when the stream has grown nice and warm we stepped underneath and let all the sweat and sex clinging to our skins wash away. I filled my hand with liquid soap and began washing Sara's beautiful body, starting at her neck and working my way down. Jessie joined in and I washed her back as Jessie washed her front. We took our time, making sure to get every nook and cranny squeaky clean. Sara moaned and writhed when Jessie and I reached her pussy and ass. After teasing and rubbing around the puckered little hole between her sexy cheeks I slipped a finger inside and Jessie did the same with her pussy. I could feel Jessie's fingers through the thin membrane of flesh as we alternated our strokes, I would pull out while Jessie pushed in, then she would pull out while I pushed in. We had her cumming in less than five minutes.

Jessie then switched places with Sara and the two of us began washing our t-girl guest. Jessie made sure that I washed her front. I began with her shoulders as I had with Sara, and I slowly made my way down to her full breasts. My hands lingered there, drawing wet circles around the nipples. After a few minutes I moved down her flat belly and shapely hips. Then I came to the focal point; her long, thick penis. It was already at half-mast by the time I got there, but after a few short strokes of my hand it was at full attention; ten, maybe eleven inches, thick and veiny.

I felt bolder this time, encouraged by what I had done with Jessie earlier on the beach. This time, without hesitation I took the head of her cock in my mouth and began pleasuring her impressive member with my lips and tongue, teasing the sensitive flesh. My jaw was stretched wide as I tried to accommodate her considerable girth, and as before I could only take about half of her ten inches. I looked up as I slurped on Jessie's meat and saw the two beautiful women I was with looking down at me. Sara's face was a mask of barely restrained lust while Jessie wore a triumphant, almost smug look. She knew she had me right where she wanted me. Her precum started to flow and I readied myself to take her load. But before she blew in my mouth she pulled away, took me by the shoulders and stood me up.

"Now let's get you clean." Jessie declared.

Jessie turned me around and I put my hands on the wall. I closed my eyes and savored the feeling of warm water and two pairs of feminine hands gliding over every inch of my skin. Fingers massaged the muscles of my neck and shoulders, and then worked their way downward, over my back, ribs, stomach and hips. Two hands then pulled apart my buttocks, one began gently stroking my cock and a fingertip slowly circled my anus. The finger traced ever smaller circles until it rested right on my tight opening, and then it began to push inside.

I knew the feeling well. Sara had slid those lovely, slender fingers of her into my ass many times, as well as all sorts of toys. I relaxed and my sphincter muscles yielded, allowing the finger entry. It slid in and out an inch or two, each stroke sending a gentle wave of pleasure through my lower abdomen. My ass was fully accustomed to the intrusion when it withdrew and was replaced by two fingers. The process repeated with gentle in and out strokes stretching my asshole. The two fingers were replaced with a third, which is as many as Sara had ever put inside me. A fourth finger was then added, stretching me open as far as I had ever been stretched. I endured the discomfort and concentrated on relaxing my anal muscles and soon the pain faded.

The fingers twisted inside of me and curved until the fingertips pressed against my prostate and began a slow, firm massage of that sensitive gland. The combined sensations of the fingers rubbing against my anus and prostate were beginning to cause tension to build in my groin and for my ass muscles to involuntarily spasm. Each spasm of my ass caused the fingers to press harder on my prostate, driving my arousal higher. My cock was only semi-hard but the precum was flowing from the tip. Suddenly the fingers withdrew and my ass felt empty. I knew that wouldn't last long, though.

The three of us dried one another off, our bodies pink and clean from the hot water. We then went together to the big bed which had been made with fresh sheets since we left earlier that day.

"You should find a nice spot to watch from." Jessie said to Sara. "He's all mine." Jessie grinned wickedly and pushed me back on the bed. I barely got comfortable before she grabbed my legs behind the knees and pushed them up to my chest. I was about to beg her to go slowly, thinking she was just going to plunge her cock into my asshole. Instead she lowered her head and began sucking on my balls, the skin of my scrotum hanging loosely from the heat of the shower. Her tongue worked lower and lower, across my scrotum to the sensitive taint and then finally to my tender asshole. For the next few minutes Jessie rimmed my ass, swirling her hot pink tongue around the wrinkled opening before venturing inside. The sensations made my cock go rigid.

Jessie straightened up and I saw that she was now fully erect. Her thick girlcock was ridged with veins, crowned by a blunt purple head with a glistening drop of precum at the tip. She reached out and I saw that Sara was waiting there with a bottle of lube. Rather than hand it to her, Sara squirted some into her hands and then proceeded to coat Jessie's ten inches with it. Sara then turned to me and worked some into my waiting asshole. She then sat back and readied herself for the coming show. The gorgeous amazon t-girl looked down at me, her next conquest.

"What am I about to do?" she asked knowingly.

"You're going to fuck me." I tried to keep the quaver out of my voice. My stomach was churning with a mix of nervousness, fear and excitement. It had been a long time since I had felt that feeling, but I was committed and ready to do the deed.

"Tell me you want it, Gary. Tell me you want me to put my cock in your ass." Her voice was low and husky, filled with lust.

"I want your cock, Jessie. I want you to fuck my ass." I replied, and meant it.

"Then that's what I'm going to do."

Jessie pressed the thick helmet of her cock to my ass and applied slow, deliberate pressure. The combination of the lube and the stimulation from fingers and tongue had loosened me up, but the head of her cock was still wider by half an inch or more than anything that had ever been inside me before. Jessie's face was a mask of lust but, expert that she was at taking men's cherries, she went slowly, never losing control. Finally, after a minute of pressing and poking my anus yielded to the think invader and her bulbous cockhead eased inside.

I gasped at the feeling of being stretched so wide. Jessie stared right into my eyes, watching for signs of pain and began the long, slow inward thrust to bury the remaining inches of hard meat inside me. It never quite felt like pain, but there was definite discomfort, like a muscle the day after working out too hard as my sphincters tried to stretch wide enough to accommodate Jessie's massive penis. My own cock softened even as Jessie's disappeared, inch by inch, into my tight anal cavity. I could feel every ridge and vein as my tender insides were stuffed full.

"Holy shit!" I heard Sara whisper. I looked over to see her reclining against a pile of pillows, stroking her clit. The sheets beneath her were damp from her juices. Jessie grasped my chin gently between thumb and forefinger and turned my face back to hers.

"How much is inside me?" I asked. Beads of sweat had appeared on my forehead.

"Almost eight inches." Jessie replied with a crooked smile.

Eight inches. That was the length of the longest dildo that Sara had ever put in my ass, and Jessie had at least two inches left to go. Once more my shemale lover resumed her inward pressure and her cock opened virgin territory as the last two inches penetrated my anus. My anal walls stretched tight around her impressive dick. Her hips came to rest against my ass cheeks and there we stayed motionless for the next few minutes as slowly, almost imperceptibly, my anal muscles loosened and the discomfort faded.

I had taken the anal virginity of one of my girlfriends before Sara so I recognized that Jessie was trying hard to make the process as painless as possible. She saw from my expression that the discomfort had faded and now all that I felt was an incredible fullness. Carefully, Jessie began to withdraw her cock from my ass, just a couple of inches, before easing it back in. She repeated this over and over until she was sure that I was accustomed to it and then began making her strokes longer, out four inches, then six and finally all of her hard meat out of me except for the head before pushing back in.

"Your tight little boy pussy feels so fucking good. I can't believe this is the first real dick you've let in there. This ass was made to be fucked." Jessie moaned as she gave in to her lust, picking up speed with her thrusts.

My ass was throbbing with pleasurable sensations. The inner walls of my rectum hugged Jessie's cock like a glove and each motion of that monster, in or out, caused pleasurable friction and the sheer size of her was putting great pressure on my prostate. Once more the precum was flowing and I reached down to stroke my hardening cock. Jessie slapped my hand away.

"No. You get your pleasure from my cock, not yours." I did as Jessie said.

The beautiful Nordic shemale then gave herself over to her passion and began fucking me with long, smooth strokes. I reached up and took her large, firm breasts in my hands, stroking and pinching her nipples between my fingers. She gave me a wink and picked up the pace of her fucking. My insides spasmed each time her thick head glided over my prostate and my cock was now fully erect, though I resisted the urge to begin stroking it.

"There's nothing like it, is there Gary? Nothing like being fucked by a real cock." I had to nod in agreement.

"I have yet to fuck a guy who told me afterward that he was never going to do this again. All of them end up loving getting fucked by any hot t-girl or hung stud they can find."

I could see her point. She used her cock expertly and I had to admit it felt great.

Jessie's fucking started to become wild, frenzied. I could see by the look on her face that she was close to cumming and I waited to feel the first load ever shoot into my bowels. Like Sara would, I began milking her cock with my ass muscles, squeezing and releasing in time with her thrusts. She finally threw her head back and groaned. Her cock flared and jerked, growing even thicker as the first squirt of hot cum blasted against my guts. Jessie came like a woman, longer than a man normally does. For about twenty seconds she bucked and thrusted until her orgasm subsided and she collapsed on top of me, totally spent.

Both of us lay still, panting for breath with drops of sweat rolling down our skin. Her cock had ceased its assault on my innards but it didn't seem to be shrinking just yet.

"That was fucking hot!" Sara declared.

After a couple of minutes I regained my strength. My insides were warm with satisfied pleasure, even though I hadn't cum. I could feel Jessie's cum flowing inside me along with her still fully engorged cock. I began to move to get out from underneath her but she held me in place.

"Where do you think you're going?"

"What's the matter?"

"We're not done, stud." Jessie's wicked smile returned. She cupped her large breasts with her hands. "These tits aren't the only way I'm like a regular woman. I can cum over and over. We've got plenty more fucking to do."

My eyes went wide at the thought that this was only the prelude. Before I could think of anything to say or do in response Jessie leaned over me and pressed her lips to mine in a deep, passionate kiss. Her tongue moved insistently, fucking my mouth just as her cock had fucked my ass (and was about to again!).

Jessie broke the kiss and grabbed my legs. She started to turn me over, careful not to let her cock fall out of my asshole. The corkscrew sensation of my ass twisting around Jessie's cock was a whole new kind of pleasure, and the load of cum in my ass added extra lubrication.

A moment later I was on all fours with her giant member still buried inside me. Having been loosened and lubricated, Jessie used none of the restraint she showed earlier and began fucking me with long strokes. This new position created all new sensations as her cock continued to churn my insides.

I looked up and made eye contact with Sara. She was sweaty and her hair disheveled. Her pussy was red, wet and swollen and she had fingernail marks on her breasts. I was so focused on Jessie hammering away in my asshole that I had scarcely noticed Sara working herself over on the other side of the bed. She only liked it rough when she was especially hot so our little show must have sent her through the roof.

Each thrust of Jessie's cock made my insides feel like they were getting a deep tissue massage and the continuing pressure on my prostate was causing my cock to drip precum like a leaking faucet.

"His mouth is free, you know." Jessie said to Sara. "Now that I've got him broken in there's no reason he can't give you a good time too."

While Jessie was busy reaming my tender asshole with her remarkable tool Sara scooted herself closer and closer until her hips were right under my head. The musky scent of her and the heat of her already well stimulated pussy washed over me.

I plunged in eagerly. Eating Sara's pussy was like French kissing. The skin was smooth and hairless and slick with her natural moisture. My lips and tongue glided over the flesh as I delved into her delicate folds, seeking the bud of flesh that was like a tiny sexual bull's-eye. She started to squirm and moan.

Meanwhile, my own pleasure was beginning to build. Jessie was angling each of her thrusts to put maximum pressure on my prostate. Her experience fucking men's asses was evident and she was right about what she said earlier. Her cock was giving me enormous pleasure. It was like the tension of an orgasm that built up in my groin, except that it was now building in my ass.

Every one of my senses was on fire. The sweaty musk of sex was thick in the air. Sara's salty-sweet taste coated my tongue. The moans of the two beautiful women in bed with me filled my ears. My eyes feasted on the beautiful body of my girlfriend in the throes of my oral pleasuring, flushed and glistening with sweat. But above all else I could feel Jessie's enormous cock splitting my ass wide and doing a number on my prostate.

Sara was the first one to cum, her juices flowing freely to run down my chin. I continued to lavish her clit, sustaining her climax for as long as I could until she couldn't take any more and pushed my head away. She scooted back up against the pillows, leaving me and Jessie.

The tension building inside of me was approaching critical mass. After another minute of Jessie's relentless fucking my groin suddenly tightened and all the muscles in my body began to flex in rhythm.

I felt my eyes roll back and a wave of euphoria washed over me. A moan that was nearly a scream erupted from my throat. To my amazement, without once being touched, my cock shot a huge load of cum onto the sweaty bed sheets. When the ecstasy passed I heard Jessie giggle.

"That's what I was talking about at the beach. Every man should know what it feels like to cum from being fucked."

With that her hands tightened on my hips and she began fucking my asshole with all her might. She was right about what she said earlier. I realized that until now the way she had been fucking me was thoughtful and unselfish. If she had wanted to she could have rammed her cock into me and fucked to her heart's delight without giving me any consideration. I finally understood what she meant about straight men learning to be more thoughtful to their lovers by being ass-fucked at least once.

But now that I had cum she gave herself over to her passion and fucked me with abandon. The sensitive flesh of my anus was on fire as the massive column of girl meat pistoned in and out, again and again. Her hips slapped against my ass cheeks over and over and the friction of her cock against my anal walls was filling me with heat.

Finally Jessie buried her cock to the hilt and began using quick, short strokes. She raked her nails down my back and came once more, spraying a second torrent of girl cum into my already full rectum. Her thick, salty jizz started to leak out from my cock-stuffed asshole. She draped her body over mine, her tits pressing into my back and her soft warm breath against my neck.

I remembered many a time after Sara and I had made love I would lie on top of her, still inside her, catching my breath and she would just have this relaxed, gratified look on her face. I finally knew what she felt. Knowing that Jessie had found a moment of perfect delight inside me gave me this incredible sense of contented satisfaction.

After a couple minutes Jessie put her hands on my back and pushed herself back up. But rather than ease her still erect penis out of me she pushed me down and onto my side, careful to leave herself still buried in my ass. My eyes widened. She was going to go again. My ass was incredibly full and kind of sore from the battering it had already taken, but I had come this far and I was determined to see it through.

I was lying on my side. Jessie was straddling my right leg and my left was pushed up to my chest. Her smooth balls rubbed on the inside of my thigh as her cock began sawing in and out once more. Jessie let her hands roam freely over my body, caressing my stomach and chest and pinching my nipples.