tagTranssexuals & CrossdressersNo Thank You Ch. 04

No Thank You Ch. 04


I woke the next day, in my warm bed staring up at the ceiling above me. It was raining outside, I could hear the water tapping against my window; groaning I sat up and sighed.

Lying beside me was Sarah. After we ate our pizza the previous night, Bryan decided to get back into his female clothes, wig included and we hung out and played video games in the living room for a while. I tried my best to shake the confusion that I was swimming in, inside of my head but it had stayed with me the whole night.

Still, I did not resist when she asked if she could sleep in my bed with me; I was attracted to her, I was falling for her and I wanted to be near her, I was just so confused at the same time.

The biggest question on my mind, was did this make me gay? I could not come up with an easy answer for that. Maybe there was no easy answer. One might say if I were attracted to her because she looked, sounded and acted like a woman then I was not gay.

If I were attracted to her even when she was not dressed up, when it was Bryan instead of Sarah, then I would be gay. If I were attracted to this person' either way then that might make me bisexual; really' though, I did not think that mattered.

If I were gay for liking a cross-dresser then I was gay and that was that. It did not help much that we had gotten back into it last night before we went to bed. I laid down thinking we would just cuddle for a little while then fall asleep, but I was completely wrong.

She got in bed and we cuddled for a bit but then we started kissing and making out and before I knew it we were both so horny, we wound up fucking again. I don't' think she planned that to happen though. I think it was just as big of a last minute decision for her as it was for me. So now here we were, the next morning...again, in bed together completely naked and my head was spinning with confusion.

I glanced over at her; she still had the wig on and the makeup to. I sighed and threw my legs over the side of the bed, got up and started getting dressed. I walked out of the bedroom and out of the apartment all together and made my way outside into the cool November morning air. I needed to take a walk, to clear my head and try to figure out what I was going to do next.

I took a trip down to Penn landing and sat there for a while, just watching the water and taking in the scenery trying to clear my head and get a grip. As I sat there, my cell phone started to ring in my pocket. I reached in and pulled it out; the caller ID read "Bryan."

I sighed, and pressed the talk button. "Hello?"

"Hey...where are you?"

I hesitated for a few seconds and cleared my throat. "I took a walk down Penn landing." "Are you okay?" he asked sounding concerned.

"Yeah, yeah I uh...I don't know. I just needed to think about a few things."

There was a moment of silence on the other end of the phone. I think he could tell by my response as well as the sound of my voice what was really going on; he could tell that this was bothering me now, that I was confused and that it was really playing with my head.

He must have known this was going to happen, I mean shit, I was straight one minute and the next I was having sex more than once with not just my gay male roommate but' my gay male roommate who liked to cross-dress and act like a woman. What did he expect me to feel like once all of the fun wore off and I realized what I had been doing? "Listen," he said.

"I know what's going through your head. I just want you to know, whatever your' thinking about its normal after everything we've done."

I guess he did understand, thankfully.

"Why don't you come back to the apartment and we can talk about this. I think it's time we discussed it anyway."

"Yeah...alright, I'll be there in about thirty minutes."

I hung up the phone and sighed. I took in the scenery one last time, stood up and started walking back to our apartment on South Street. When I got there, I unlocked the door and walked up the steps to find Bryan sitting at the kitchen table drinking a cup of coffee. There was another cup sitting there and I assumed he had set it there for me for when I got in.

"Hey," he said motioning for me to sit down. I did and I picked up the coffee mug and took a sip before sitting it back on the table and smiling over at him.

"So, talk to me. What's going through your head?" I laughed and shook my head slowly, trying to figure out where to start.

"I don't know; a lot."


"Like what does this make me; am I gay?"

It was Bryan's turn to laugh now, and he leaned over the table smiling at me and I could not help but laugh too. "Do you think it makes you gay?"

"See, now that's not a fair question. I wouldn't be asking if I knew."

"Guess you have a point. Listen; are you attracted to me only when I'm' dressed as Sarah? Or do you find yourself attracted to me when I'm myself to?"

I thought about it for a moment. That same thought had been on my head already as it was and I still did not have an answer so it wasn't good that he' was asking me right now. I didn't' know what to say really. He stood up suddenly, walked around the table, and plopped down on my lap and draped his arms around my neck.

My heart was pounding in my chest so hard I could practically hear the thumping of it blasting in my ears. Before I knew it, Bryan leaned in and pressed his lips to mine, kissing me softly at first then becoming more passionate. He slid his tongue past my lips and I kissed him back for a few seconds before pulling away.


"Well what?"

He laughed. "Did you like kissing me when I'm not Sarah?"

I was still so god damn confused and I guess he could tell because he leaned in and kissed him again. He pulled away and smiled at me.

"Tell you what," he said. "We're going to help you figure yourself out tonight; be ready by 7:30 I'm taking you out."

"Out; out where,"

"To a gay' club up around 15th street. It's called Woody's."

We got to the club around 8:15. We walked from our apartment up to 15th street so it was a bit of a hike, not to mention the fact that Bryan took his good old time getting dressed up as Sarah. Instead of wearing his typical blonde wig, he was wearing a black one and had' also applied black eyeliner and red cherry lipstick. I knew it was cherry because he had kissed me just as we were about to walk out of our apartment door. As we walked into the club, I was not shocked to see so many gay men dancing and having conversations and drinking.

There were also a large amount of transsexual women, cross-dressers and transvestites. I noticed after a few moments that there were a few eyes locked on me as we walked towards the bar area of the club. We took a seat and Sarah ordered herself a beer and one for me to. I tried to relax as a group of people came over obviously friends with Sarah, and they started talking. One of the men with the group of people took a seat next to me and offered to buy me a drink. I glanced over at Sarah as if trying to get her permission; she smiled and nodded her head as if to tell me it was okay.

So I nervously accepted and the man whose name was Jay ordered me a Jack and Coke. After about an hour, I was starting to feel a little buzzed and loosening up, laughing and cracking jokes. That's' when Sarah came over and sat down and started talking with both me' and Jay. A couple of shots of Jack and a few more mixed drinks later and I was' really starting to feel the effects of the alcohol.

Sarah kept walking away and leaving Jay and me to talk then coming back over and joining in before walking off again after a few minutes.

The drunker I started to feel, the easier it seemed to get for Jay to flirt with me and have me go along with it; if Sarah was trying to see if I would hook up with a guy and like it, it wasn't going to work. I was drunk, that was how I had wound up sleeping with her the first time, so how was I really going to know if I did it while I was drunk.

Eventually, Jay's intentions were' made crystal clear when he slid off his bar stool and sat down on my lap. He leaned in and kissed me on the lips, and drunk as I was I kissed him back; he slid his tongue into my mouth deepening the kiss and I embraced him.

Sarah walked over as we sat there making out, and I felt her hand on my shoulder drawing me away from the kiss. I looked up at her and she smiled down at me leaning in and kissing me; now I had Sarah and this guy both coming on to me at the same time and I was feeling really' horny. They pulled me out to the dance floor; Jay was behind me grinding against me with his arms around me while Sarah was dancing in front of me smiling the whole time.

She moved in and started making out with me while Jay started kissing me on my neck and reached around to start rubbing my cock through the fabric of my pants. When the song ended, we left the club, Sarah and Jay pulled me outside and he walked down South Street back to mine and Sarah's' apartment.

I knew what was going to happen when we got there, and I was so damn drunk it did not make a difference to me anymore.

As soon as we got there' we were all, all over each other taking turns making out and removing our clothes. They pushed me onto my bed and climbed in with me, Sarah kissing me on the lips while Jay kissed his way down my chest and stomach to my groin. I could feel him kissing, stroking and teasing my already hard cock before wrapping his lips around it and I moaned throwing my head back as he took me all the way to the back of his throat.

As Jay went to town sucking my dick, Sarah got off the bed and walked into her bathroom leaving me and' Jay alone. About four minutes went by and she still had not come back yet; Jay finished sucking me off and moved up to start kissing me again. I could taste myself on his breath but it did not bother me really.

We made out for a few minutes and then he sat on my chest, his weight pushing down on me for a second before lifting himself up and leaning forward. He rubbed the head of his cock against my lips and all over my face before pushing it past my mouth and to the back of my throat. I gagged and inhaled the smell of sweat from his balls as he started pretty much throat fucking me.

The bathroom door opened again and instead of Sarah, Bryan walked into the room still naked but he had washed off all of his makeup and done away with the wig.

Now it was just Bryan, and this would be the first time I was going to do anything sexual with him while he was not dressed as a woman. He climbed into the bed while Jay continued throat fucking me and him and Jay started kissing. Somehow, we all wound up in this crazy ass position with me on my back but my head was hanging over the edge of the bed while Jay was standing over me feeding me his cock.

He was also leaning over me so it was kind of like' we were in 69, and Jay was laying long ways across the bed at my feet while Bryan went down on him. Somewhere along the line, Jay slipped out from under Bryan and came around behind him, climbing up on the bed over me while I continued sucking Bryan's dick and now Bryan was sucking mine at the same time. Jay got up behind Bryan, his ass in the air and I had the perfect view from underneath of them as Jay carefully guided his big fat cock into Bryan's tight little asshole.

My dick started throbbing, this entire scene was turning me on even more and the friction of Bryan's mouth around me made it even better. Jay started fucking him, thrusting in and out' pounding his ass with long hard strokes and every time he thrust into him Bryan would moan against my cock causing me to moan against his.

This had to be the perfect definition of a threesome. The first time I had, had a threesome and it was with two other men; it was pretty' fucking hot to. By this point, the alcohol was beginning to wear off and I was pretty much thinking with a clear enough head to know that I was enjoying this situation.

Bryan must have known what he was doing, he set this up perfectly; I had though he wanted me to take it in the ass from Jay but I had no idea he was arranging a threesome. Three minutes passed by and suddenly, Bryan started moaning really loud; he stopped sucking me off and gasped for air as he released my dick and instead of sucking he wrapped his hand around it and started jerking me off.

He moaned louder and louder while jerking my cock and finally, I could taste his warm sticky cum filling my mouth. I choked and gagged a little but swallowed it all and seconds later, I heard Jay start moaning and grunting signaling that he too had just ejaculated. He pulled slowly out of Bryan's asshole, his cum leaking out of the other man's ass and dripping down on my face. I removed Bryan's dick from my mouth and called out in pleasure as I started to cum, shooting my load all over Bryan's hand and face.

We pulled away from each other and Bryan shoved me face down onto the mattress and got behind me. I moaned as I felt him get on top of me and I could feel his dick rubbing against my asshole. One little thrust and he was all the way inside of me, fucking the living shit out of me the bed creaking underneath of us. As he fucked my ass, Jay sat down on the recliner in the corner of the room and started jerking off trying to get hard again.

Bryan started to cum, pumping me full of his semen and pulled out collapsing beside me; we lay there for a few moments and Jay smiled over at us.

"You know what I would really like to see now?" he asked. "I want to see Tom fuck you in the ass now,"

Bryan seemed pretty up for the idea of that, he rolled over on top of me and positioned his ass right over my dick. He sucked in a breath of air and moaned as he lowered himself down on to me, taking me inch by inch into his asshole, which was still pretty' loose from when Jay fucked him earlier.

When I was all the way inside Bryan started bouncing up and down on me while stroking his own dick.

I flipped over on top of him wrapping his legs around me so that now we were in missionary position. I pounded his ass as hard as I possibly could, both of us moaning in pleasure as I did and that's' when Jay came over and got behind me. I knew what was coming so I stopped fucking Bryan so hard in order to make it easier for Jay to penetrate me; he got behind me, grabbed my hips and guided his cock into my asshole.

I moaned as he slumped forward on top of me causing me to push deeper into Bryan. Each time Jay would pull back, I would too, then I would thrust forward back into Bryan and Jay would follow slamming himself balls deep inside of me. We did not last long at all; two minutes maximum before I exploded filling my roommate with my' cum and we stopped for a moment so he could slide out from underneath of me.

Once he was out, Jay continued to fuck me, pumping my ass with hard strokes for another two minutes before he came as well.

We all collapsed on the mattress once we were done and finished; after just two minutes of laying there' Bryan and Jay were both sound asleep and I was drifting slowly but surely.

I could not believe what I had spent the last few days doing; I'd' had sex three days in a row and it had to be gay sex. Who would have ever seen that coming?

The next morning I woke up to find Jay was gone and Bryan was to. I quickly got out of bed and started searching for my towel, grabbed' hold of it and ran into the bathroom to take a hot shower. I cleaned up best I could got' out, dried off and got dressed. I made my way out into the living room and found a note on the kitchen table that Bryan had left me.

Tom: Went shopping. Be back in a couple of hours; Jay went home. We can talk about what happened last night when I get home. Bryan.

With nothing else to do, I set the note back on the table and set about making myself something to eat for breakfast. I cooked eggs, bacon, sausage and toast and sat down at the table to enjoy my morning meal before doing the dishes and plopping down on the living room recliner. I turned on the TV and powered up the Playstation3; I was going to spend a little while playing a few video games until Bryan got home from the supermarket.

When she did get home, I started helping him unpack all the groceries; He was dressed as Sarah wearing the blonde wig when he walked in. We talked about the game I had been playing and something that had happened at the supermarket while Sarah was shopping until we were' done putting everything away. Now that, that was out of the way it was time to discuss what we both could not seem to get off our minds for the life of us.

"So about last night," Sarah started.

"Yeah...last night." I replied.

Things felt a little tense for a few moments until she cleared her throat and continued' on.

"What um...what did you think?"

"Oh," I said laughing nervously. "I uh...really, really liked it...all of it."

She smiled and listened as I continued' on.

"I mean I liked everything that we did the last few days. Last night though, that was just fucking hot...can't say I'd do it with Jay again though."

Sarah laughed and sat down at the table across from me.

"So, what's the deal then? Do you think your gay or not?"

I knew what this had been about now; she had set that all up for a purpose. She was trying to help me figure myself out by hooking up with me while not dressed as Sarah and' also having another guy' in the situation. Not only had I slept with one guy' who happened to be my roommate at that, but I had also slept with two men at the same exact time.

That had to mean something, and I was sure it did and that was fine with me at this point. "I don't think so," I said finally. She looked at me curiously and I smiled. "I don't think I'm gay; still like girls. I just sort' of know it in my head, I am not done with women or anything like that it's' part of who I am. I do like men now though too; I also like men who like to dress as women."

She laughed at me and I moved closer to him and sat down smiling over at him.

"So no I'm not gay, pretty sure of that. I guess I am bisexual though."

"And your' okay with it?"

"Yeah, yeah of course; I mean why run from it when it's who I am. I guess I've' always felt different, I just never really understood what I was feeling and did not put two, and two together. You kind' of helped me realize what was always there."

We were quiet for a few seconds and he stood up and stretched before looking down at me. There was something on her mind, and I worried that somehow I had upset her or something, though I could not be sure how I could have done that.

"What's wrong?" I asked.

"Nothing I uh...just wanted to ask you something now that you understand yourself and all that; do you think you and me...we could um."

I knew right away' what he was trying to ask, I stood up and pulled her into my arms kissing her on the lips.

"Does that answer your question?" She laughed and kissed me again leaning into me and I wrapped my arms tighter around her. "I'd love to be with you." I said.

"Great. I am really' glad that we are together; no more sex for a couple of days though," she said. "Maybe even a week or two; god my asshole needs a break."

We both laughed and I kissed her on the lips.

"Mine to,"

I was glad that all of this had happened. I'd had sex three days in a row with my roommate a guy who liked to dress as a woman, and it had opened my eyes to a whole different side of me that I had no idea existed. Now here we were, together. I was in a gay relationship with a cross-dresser and I did not know what the future held in store for our relationship but' whatever it brought to us we would be happy together.

I was sure of that much.

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