tagTranssexuals & CrossdressersNo Thank You Ch. 03

No Thank You Ch. 03


I lay there on my side, with Sarah behind me her arm draped over me; we were in a spooning position and I could feel her hard cock pressing against me, probing my asshole. She started kissing me on the neck while playing with my nipples; I knew what she wanted. She was really trying to seduce me into it to. Until now I had, had no problems at all with any of the things we had been doing together. Hell, I had even sucked her cock and enjoyed that, but the idea of bending over and letting her stick her big fat dick in my ass...that sort of made me a little uneasy. I had seen a lot of anal sex videos, of course, all of those videos had girls getting' fucked in the ass; I had never watched a gay porn in my life. Regardless, most of the videos I had seen the girl always made it seem so god damn painful; sure about midway through they would start to seem like they were enjoying themselves but it was the wait they had to endure until it slipped from painful to pleasurable.

She must have known I was nervous because she seemed to be trying pretty' damn hard to convince me to give her what she wanted. I moaned as she sucked my neck and blew in my ear, sending chills up and down my spine. She was driving me crazy, and I was really trying to figure out if I wanted to go through with this or not.

"It'll only hurt for a few seconds, I promise."

She obviously knew what I was worried about; yet strangely, as she whispered that in my ear and ran her hand soothingly over my chest at the same time, I could not help but relax. It dawned on me then; I had only known Sarah for a day that was true.

However, Sarah was not really Sarah; Sarah was really Bryan and I had known Bryan now for two and a half years. By this point, I felt like I should be able to trust him pretty' well, so what the' hell was I so afraid of? As she continued pressing up against me I caved in and turned over onto my stomach' and wrapped my arms around the pillow under my head.

She must have gotten the point because Sarah got up and reached for the lubrication and I jumped at the feeling of the cold stuff hitting my asshole. Then I felt something stiff but not big pushing into me; it wasn't' big enough to be her cock, and I realized after a moment it was her finger.

She worked her index finger deep into my ass and started massaging my prostate gland; I moaned as she rubbed up against it and I felt my cock start to go hard between me, and the bed. After a few moments of fingering me, she pulled out slightly and I felt my asshole stretch as she worked an additional finger back into me.

She now had two fingers knuckle deep in my ass, stretching me wide and playing with my prostate. It felt good but I also had this strong feeling of fullness and I realized, if it felt this strange just having two fingers inside of me how out of place was it going to feel when she actually started fucking me?

I felt her pull her fingers from me and she reached for the lube, applying' more of it to my asshole and I heard an additional squirt indicating that she was applying some to her cock as well.

I took a deep breath and tried to relax myself; I knew from experience of fucking girls in their asses that if you were to tense then it would make it all the more difficult and painful. I braced myself, gripping the pillow as I felt her climb over top of me and she started running both hands up and down my back trying to help me relax.

"Are you ready?" she asked softly.

"Yeah; just go easy okay?"

"Don't worry baby. I will."

I felt one of her hands move away from my back, she used it to grab her cock and I felt the head of her big shaft pressing against my well' lubricated and slight widened asshole. She applied pressure using her hand to guide herself' into me; I felt myself stretching wider and wider and the feeling of fullness returned but a lot more noticeable. She inched her way into me and I felt as though the feeling were becoming overwhelming.

I bit my lip, shut my eyes and' held my breath trying not to cave and give up to easily on this.

"Are you okay?"

"Yeah," I replied.

"Do you want me to stop?" she asked.

I could tell by her voice she was not annoyed at all with me; she sounded more concerned and I could hear it behind her words that she really cared.

"No, it's okay" I said. If she cared that much about me, then she deserved to enjoy herself so I would at least try to stick it out a little longer.

She continued inching her way into my tight asshole until I felt her full body weight on top of me and I could feel her balls pressing against me. She was all the way inside of me now and' just staying there not moving an inch waiting for me to adjust to the sensation of her huge cock deep inside of me.

"You okay?" she checked.


With that, she lifted herself up just slightly, pulling her cock about halfway back and then driving it all the way back into me again. I gasped at the feeling of her moving out and then back in and then she repeated the same action a second time. By the third thrust, I could feel a strange hot feeling deep inside of my asshole with each thrust that she delivered. She was fucking me softly, making extra sure not to hurt me in any way and I could feel the dull pain beginning to subside as the pleasure started to kick in.

When she realized I was starting to enjoy myself, I noticed she had started to pick up the pace a little and was starting to fuck me just a little harder and faster. As my cock started to get really' hard, I arched myself up off the bed slightly so that my ass was sticking out. She took advantage of my cooperation and grabbed me by the hips getting a firm grip; she started fucking me harder and faster now, breathing heavily as she slammed in and out of me.

I started pushing myself back against her to meet each of her thrusts. I could hear the sound of our sweaty bodies slapping together and my cock was throbbing by now; there was this strange sensation in the pit of my gut and it kept growing and growing. It felt like something huge was about to happen and I found myself praying that I was not about to have an accident from all this stimulation.

It felt like my insides were being twisted but in a good way if that makes any sense at all; I moaned and embraced the sensation and could not help but call out to her and beg her to fuck me harder.


It came out in a low raspy voice and she almost didn't' hear me.


"I said...harder...fuck me harder!"

"Tell me what you want me to do baby,"

"Oh god...agh, ugh, ugh, fuck' me harder!"

She did just as I asked and started really pounding away at me now; the bed shaking underneath of us making the familiar creaking sounds of a couple having some really intense sex.

We had thin walls and I was sure by now at least one of our neighbors could hear what was happening. The problem there was they would hear me begging to be' fucked harder instead of a girl uttering those words, and I was sure that later on one of my neighbors would probably be giving me an odd look when I ran into them.

I gasped as that twisting feeling over took me, and the tip of my cock started to burn as the room began to spin. I'm' not sure how to describe the feeling really.

It felt like my asshole was squeezing her cock, clenching and unclenching over and, over again. The spasms became more powerful and as they did, my cock started to shoot a hot load of sticky cum all over my bed sheets.

"Oh shit," I moaned loudly.

Sarah was pounding me now and now that I had reached my orgasm, she could stop holding back on herself. A few more powerful' thrusts and' grunting and moaning and she buried herself, balls deep in my asshole and exploded. Pumping me full of her cum before collapsing on top of me and we' both sank into the mattress my face buried in my pillow.

We were out of breath and both of us were covered in sweat, exhausted and I actually felt kind' of hungry. I could feel her cock starting to go limb inside of me and she pulled out rolling over and dropping back on the mattress at my side. We lay there for a few minutes, just trying to collect our thoughts before I turned over and smiled at her. She smiled back and moved closer to me, resting her head on my chest as we finally relaxed and managed to catch our breath.

"That wasn't so bad was it?" she asked

I laughed, and ran a hand through my hair staring up at the ceiling. "Felt pretty fucking good," I said. I could hardly believe it myself but it was the honest' truth, I really had enjoyed every minute of what we just did.

We must have drifted off after a few minutes because I lost track of time and when I woke, I glanced at the clock and was surprised to see that it was almost 9:00 at night. We had slept practically the entire day after our little fuck session ended and I was starving now.

I sat up on the bed and that's' when I noticed Sarah wasn't' beside me anymore. I rolled out of bed slipped into my boxers and made my way out into the living room to find Bryan sitting on the couch watching TV.

"I see your' awake finally," he said smiling at me.

"Just woke up; I'm starving' to."

"I made a sandwich about two hours ago; we can order pizza if you want."

I grabbed a few of the menus that we kept in the kitchen drawer and after a few minutes, we settled on the closest pizza shop that we could find and ordered a large pizza with extra cheese. I sat down on the couch while we waited for the food to get there and could not stop thinking about what we had done earlier and the night before.

All of this was so fucking crazy, last night there was kind of an excuse seeing as we were both so drunk and all; but today we had been completely sober and that had not stopped us. What scared me the most was that I had enjoyed all of it more then I had ever enjoyed any previous experiences of my life.

This had been some of the best' sex I had ever enjoyed; so what did that say about me if the best sex I had ever had was with another man who liked dressing as a woman? I had no idea what was in store for me or Bryan/Sarah or our future for that matter.

I just knew that right now the feeling of euphoria had worn off and now I could feel the head ache of confusion starting to kick in.

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by Newbottoms11/12/15


It amazes me how guys in these stories go from die hard straights to confusion.I wonder how many actually experiment. I'm 40 and I never experimented until I was in my 30s. I blame that on sexual frustrationmore...

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