There was never a question.

[bikeorcock]

I took a trip back to my home town of Chicago where I had made several connections on line with potential tops. I was going to go on a sex bender but I didn't know what it would look like, one guy, multiple guys, gang bang or what. I learned to not be wedded to one course of action because on line guys are flakes and you have to be flexible. I did know one thing, I was not going to go raw, I felt I had dodged a bullet by throwing caution to the wind and following my desires recently. I had tested neg and both the tops had as well so I was safe, but it had scared me into no sex at all for a while.

I had been successfully chatting with two different tops on a4a.com, one was very chatty and got into dirty chat that got me tingling and off a couple of nights, the other was on the quite side saying that he was a man of action and few words. However the few words he said and the picture of his 9" cock were all I needed. I had to slow my expectations because one never knows with on line connections if they will happen or not.

I flew in Friday afternoon. The flight was normal, only felt longer because of the anticipation for what I was going to do once I got settled in. I had three days and two nights free before I had to be anywhere or talk to anyone and I was going to make the most of my freedom. I got to my hotel suite, unpacked, douched, showered and got the room ready by laying out a big bottle of lube and condoms on a towel next to the bed and fired up the lap top.

I sent emails to the two guys I had been chatting with, they knew when I was going to be in town and where I was staying. I wanted nothing to get in my way. Both said they would be available late afternoon to early evening. Just as my lap top was making that sent email swiish there was a knock on my door. I dressed and saw a woman with a room service tray outside my door. I opened it up and she said that this was for me and brought in a tray with champagne, a fruit plate and shopping bag. I handed her a hasty tip as she left.

Just then the hotel phone rang. I picked it up and said Hello. "Did you get my special delivery?" Yes I replied. "Good, I told you I was a man of few words but of action if you are serious about what we talked about you will open the package and follow the instructions inside the package." Then he hung up.

I opened the bag and inside was a set of matching bra, panties, a white Marilyn Monroe type dress and heels. The note said "You said you were a total bottom and you wanted to be my bitch, to prove it you will put this on and email me a picture of you in this outfit. I know your room number so when I get the email I will show up at your door. -Darryl"

He hung up before I could say anything. I was thrown for a total loop! First off I have never been into cross dressing, I am a submissive bottom and get off on being a man getting fucked by a man. I told Darryl this when he asked my limits and here he was pushing them who knows what he will push on later. Second, the fact that he knew the exact moment I got into my room and had this all planned had a little freaked out, but I was impressed with it as well. Thirdly I was totally turned on by the fore thought and the direct way he did this, it was clear he wanted me and I felt myself swell with lust and pride. The clothing was from a cross dressing boutique and they were my size, I always wondered why guys ask for measurements and now I knew! I looked at them and knew that if I did this there would be no turning back, I would be submitting in a way I have never done before. I was both scared and excited at the same time.

I don't know how long I stared at the gift but I had to admit that I felt myself giving into Darryl's orders and the tingling inside of me grew to a roar. I decided to give into the desire that was stirring in me and to see where this would lead me. I stripped and slipped on the panties and the bra. I felt humiliated, but I was doing it anyway. I slipped into the dress and put on the shoes and looked at myself in the mirror. It was as silly to me as I thought and I almost took it all off but I didn't . I took a selfie and emailed it to Darryl. There was no stopping this now.

The 15 minutes before his knock were torture. I wanted to take off the clothes but I didn't, I sat with myself and reflected on how I had done something I had never done and how humiliating it was. This was the price of my lust and I was beating myself up for compromising myself. Just as I was about to take everything off and call it off a knock came at my door. I peaked through the peephole and there was Darryl, 6'2", dark caramel skin, short buzzed black hair and a very masculine handsome face. He was dressed in all black slacks, t-shirt and sports coat that hinted at an athletic body underneath. I was excited and scared as I opened the door to greet him.

He looked at me and said "You obeyed, that is good!" as he walked in and made his way to the champagne, I followed him unsure what to do next. He poured us two glasses and gave me one. We both took a couple of sips and he said "Now that I know you are willing to do. Now come her and kiss me and thank me for the gifts!"

I leaned into him and kissed him, soft at first but my lust grew and before I know it his arms were around me and his tongue was probing my mouth. I melted into him and kissed back. I felt his cock get hard in his pants and something in me gave into him and all I wanted was to please him. I straddled him so I could free his hardness through his pants pressing against my hole. With no words he undid his zipper and his hard 9" cock was out. His cock was oozing precum and he pressed himself against my hole soaking the panties I was wearing. I gasped and pushed my aching hole onto him, if I hadn't had the panties on he would have been in me. He fooled around like that for several minutes, I felt myself loosing any thought and was operating just on lust.

He pulled the panties aside and slid his cock against my hole. His warmth and hardness sent shivers up my spine. He spit on his hand and rubbed it on the tip of his cock and pressed into me. I threw my head back and gasped and as I was about to cry out he grabbed the back of my head and pushed me into his kiss, his tongue invading me as his raw cock slid into my hole. I relaxed and let gravity take over and with one long smooth push I took the full length of him.

The combination of everything that was happening to me was too much. His strong arms holding me onto him, my cock straining against my panties, his mouth on mine and me impaled on his big cock throbbing deep in me was overload! I started quivering, it started in my legs and soon my whole body was quivering. I couldn't control it! I was shaking and the pleasure I felt went from head to toe! He slowly pumped himself into me and I lost it. I shot my load in my panties. I felt the fullness of his cock in me as I constricted from orgasm. He stayed in me until my shivers passed and picked me up. I clung to him as my hole tried to eject him. He laid me on the bed on my back and put his full weight into me and reasserted his ownership of me.

He took off his coat, his shirt and quickly exited me so he coul take off his pants. I instinctively tried to get away from him but he grabbed my shoulders and pulled. me back into him. I arched my back so he could remove my cum soaked panties and he put my legs over his shoulder and slid himself back into me. It was painful but he worked himself back to the hilt slowly opening me up. My cock stirred again as he filled me. He was slow but forceful, not letting me get away and making my hole love his cock. I was in heaven. Yes I was in women's clothing and yes there I was barebacking a stranger but the pleasure I felt was worth it.

He kept up a slow grind into me, I felt myself loosen up to him more and more. He rewarded me with moans of pleasure. He owned me. I have no other words for what happened. My hole was his, my pleasure radiated from where he was in me, I could do nothing but react and take him. I had done everything he wanted, I had no boundaries, I had given him everything I had and I loved it. I only had one thing left, so I begged him to cum in me. He told me "there was never a question I would", and as I heard him say that my cock sprang back to life.

He kept up the slow deep penetration. I was opened to him as much as I could be. I was his. He lay on top of me and o wrapped my arms around him, he snaked his arms around me so I was fully engulfed by him. His humping got faster and I held on to him for dear life. He grunted into my ear and his body smothered me. I felt him arch back but I held on to him, I move my head to his face and kissed him, his tongue entered me as I felt his body shiver and his cock spasm inside me. His warm cum filled me and I clung to him taking it all. Pride and joy filled me as I felt his seed spread inside me. I would not let him go. He kept his cock in me until he lost his erection. He slid out of me and I moaned. I watched him get up and go to the bathroom, I lay there feeling his mighty semen ooze out of me. I was hard and aching for him to return. I wanted more!

[Guest JizzDumpWI]

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