For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had never done before. I have had sex outdoors before but in a secluded spot, I had only toyed with the idea of going out in a populated place. Nevertheless I agreed.
I booked a hotel room near where he lived. It was a long drive to get there, and my nerves were building all the way. By the time I arrived I was so nervous my legs felt weak, but I was excited as well and still detirmined to go through with it. I booked in and went to my room to unpack my things. I had brought some clothes that were a little less slutty than normal as I would be going out in them. I normally like latex but that seemed a little too slutty and revealing for my first time going to a bar. I had brought a short dancing dress, tights, lace knickers, high heeled ankle boots, and my strawberry blond wig. Getting dressed took much longer than normal because my hands were shaking so much that I kept smudging my makeup, and by the time he arrived, and was having a drink in the bar I was still nowhere near ready.
Eventually I got my makeup right and my hair and clothes were looking good. I stopped to admire my work in the mirror. Considering how much my hands had been shaking the results were not bad at all. My makeup went well with my freshly brushed wig, and the high heeled ankle boots made my legs look great in the black tights, and pushed my arse out invitingly in the short black dancers dress. I was ready to let Allen know I was on my way down. It took me a few minutes to build the courage to leave my room, but I had to go downstairs as I couldn't leave him waiting forever. I felt so nervous walking to the lobby in my short little dress and high heels, it felt like a swarm of butterflies were going into a frenzy in my stomach. I stepped into the bar and to my relief it was fairly empty. I spotted Allen standing at the bar chatting with another guy. He looked amazing in his skin tight t-shirt that showed off his bulging muscles.
I stopped behind him and touched him on his huge shoulder, and as he turned to me his face lit up as he looked me up and down. He looked at me in a way no guy had ever done before, almost hungry like a lion looking at a steak. It made me feel naked and vulnerable. He leaned in and kissed me hard, his tongue intwined with mine as he pulled me close to him, his strong hands on the small of my back.
''You are sexier in real life than in your pictures,'' he said. "I was worried you wouldn't show.''
I was still reeling from nerves and from his kiss so I only managed a weak, ''Thanks,'' as his hand slid down to my bum.
He pulled up a bar stool for me and I sat with my legs together and he sat opposite with my legs inbetween his. His hand went straight to my leg and he started to rub my thigh as he ordered us some drinks. More people were starting to wander in as our drinks arrived and I think he noticed me tense up as I became more nervous.
He took my hands and said, 'You are with me. Just relax,'' and kissed me again even harder and longer until everything else seemed to melt away.
He let go of one of my hands and took a sip of his drink, as he continued to hold my other hand with his and stoked my fingers. I started to relax and feel excited again. We chatted for a while about how he used to do security work in the area as we drank and he continued to stroke my fingers. Then told me to finish my drink because he wanted to go for a cigerette.
He stood, took my hand and led me outside. It was a little chilly outside and the breeze was blowing up my short dress making me feel cold but extremely horny. I hadn't smoked in years but I was so nervous that I took one anyway. My hand was shaking as he lit it for me and I told him it was because I was a little bit cold, which was a half truth, so he put his arms around me. It felt amazing to be stood on the bar patio in my little dress and my high heels with his huge powerful arms around me, and when his hands went down to my bum I almost squealed with excitement.
We went back to the bar and had a few more drinks, we chatted, and kissed and he fondled my legs held my hand. After he kissed me again so hard I almost fell off my stool, he asked if I wanted to go back to the room. I agreed, I couldn't wait for him to get his hands on the rest of me.
He took my hand and led me to the elevator once were inside he pushed me hard against the wall his strong hand going up my dress and grabbing my bum.
He kissed my neck. ''I have been waiting for this for weeks,'' he whispered. ''I want your lips around your cock.''
The lift went up four floors and I barely noticed it had moved, as his strong hand kneaded my bum so hard I struggled to keep my balance in my high heels. When the doors opened he spun me around kissed me as he walked me backwards out of the lift bumping into walls and doors as we went, until we reached my room. My trembling hand could barely get the keycard into the slot, but eventually we practically fell into my room.
Once inside I stripped off his skin tight t-shirt and kissed his smooth muscular chest as he undid his belt and slid down his jeans and boxers. He threw me onto the bed with ease and layed down on top of me his huge naked frame pinning me down. He kissed me harder than ever as his hand went up between my legs and stroked my small cock through my knickers. Then in one move of his strong arm he span me over and pulled down my tights and knickers.
I felt his tongue in my tight little hole before I realised what he was even doing. I went weak in the knees again as he tongued my ass. He stopped for a second then I felt the cold lube on his fingers as teased my tight hole. His cock felt huge as he entered me for the first time, and I let out an involuntary gasp as his helmet forced its way in.
''I love your tight, little, round ass,'' he said as he slapped my ass hard.
He pushed my face down into the sheets as he started to thrust harder. One hand on the back of my neck one on my bum his legs started to slap against the back of mine. The feeling was amazing, being manhandled with his hard cock deep in my ass as the skirt of my dress swayed with each thrust of his cock. I had never felt so helpless and horny.
''You like it hard don't you, you little slut,'' he said and slammed his cock into me hard, and then again.
''Thats a little too hard,'' I said through gritted teeth.
He pushed me down flat on the bed and layed down flat on top of me pushing it into me slowly again. He had my arms pinned as he was grinding in and out, but he was being gentle now so it was much nicer. He was heavy and I couldn't have stopped him if I had wanted to, but I really didn't want to. He kissed my neck and cheek as he continued to thrust up inside me, his cock stretching my ass until it was sliding in and out with ease.
He stopped and pulled me to the edge of the bed unil I was standing bent over, then he pushed it back in again. I struggled to keep my balance in my high heels with my tights and knickers around my thighs and his cock going in and out of me faster and faster. I grabbed handfulls of the bedsheets but could only just stand with the vigerous fucking I was getting. When he eventually erupted inside me he pushed forward so hard that my heels finally lost grip and he fell forward with me onto the bed his weight forcing his cock up inside me even further.
He eased out of me and I turned over. He kissed me again as his hands went to my cock. He began to stroke it until it was rock hard, then he moved down my body and slid my cock into his mouth. This was a strange feeling for me, only one guy had ever sucked me off before and somehow this felt different, more intense, more passionate. He didn't keep it up for long though instead he pulled me up so we were both kneeling on the bed face to face. He pulled me close, one hand on my bum, the other still stroking my cock. I wrapped my arms around his neck and then his tongue was back in my mouth, exploring. I didn't last long my cum covered his stomach and ran down his leg. He pulled me from the bed. He stood as he pushed me to my knees.
''Lick it up,'' he said smiling, and pulled my head towards his hard stomach, that was glistening with my cum.
I licked up most of it kissing his stomach and licking the drops from his thighs. His his cock started to harden again next to my face. He grabbed my head with both of his strong hands and guided his cock into my mouth. I tried to slide my lips down his shaft but his hands were holding my head still. Instead he started to thrust into my mouth hard as he pushed my head into it. I gagged a couple of times as he pumped his meat deep into my mouth his helmet finding its way to the back of my throat. I struggled to keep his cock wet so that it could slide in more easily, he was building up the speed too quickly for me to keep up. He pulled it out as he came. Most of it still went in my mouth but some landed on my face and dribbled down my cheek, that seemed to please him.
We kissed and fondled and chatted for a little longer, then he layed down on his front on the bed, so I climbed on his huge back and gave him a massage. It wasn't easy his back was so hard it was like trying to massage a side of beef, but he seemed to enjoy it. He was asleep by the time I finished, so I got changed into some naughty night wear, a silk night dress and white holdups and went to sleep beside him. I woke in the morning with him behind me one of his huge arm wrapped around my waist and his morning wood pressed up against my ass. When he woke he kissed me and told me he had to go. He got dressed as I layed on the bed watching him, my skimpy silk dress concealing nothing. When he was dressed he climbed on top of me again and gave me a long kiss. He lifted my legs and began to stroke the back of them. I moaned as he reached my ass and I could feel him hardening in his jeans again. I could see him getting visably horny, and eventually he couldn't take it anymore and tore his t-shirt back off and started to remove his jeans.
''I want your ass,'' he said eagerly.
He pulled me to the edge of the bed and lifted my legs. I barely had enough time to wrap my legs around his waist before I felt him push his way inside. He leant into me and kissed me as he continued to thrust inside. Eventually he stood and pulled my legs up so they were over his shoulders. This seemed to give him the ability to get his cock further inside me than ever and I felt like I would explode. With every slap of his hips hitting my ass he seemed to drive it a little deeper into me.
To finish off he pulled me to my feet, pushed me into the wall and took me from behind again. I tried to push back but his thrusts were too powerful and too fast and he was bouncing me off the wall. He came hard and nearly lifted me off my feet with his last thrust. This left us both panting leaning against the wall until his cock started to soften inside me and he pulled it free. This was not the wakeup I had been expecting but I wasn't going to complain.
This time he really did have to go, so he got dressed again and left me in my disheveled night dress, his cum still dribbling from my ass.
He wants me to meet him again and go out with him to some of his favorite clubs. He also mentioned maybe having sex outdoors. I couldn't say yes quickly enough. I can't wait to be in his muscular arms again.