Our Evening Together

This is my first story of a sexual encounter I had.

I was home dressed in a little magenta lace dress with sleeves that hung off my shoulders and came just above my knees. I also had a strapless padded bra, black thong panties, black garter belt with black stockings with red bows at the top. I was also wearing a cute pair of tan pumps and a reddish-brown wig. Even if I had makeup and wearing a wig, I am not passable, or as passable as I wish I could be.

I had been looking through a local sex dating site for a guy to come over and let me pamper him. After replying to a few and not getting any responses, I decided to post my own. It was a basic listing telling who I was at the time and had a pic of me in the dress I was wearing.

About an hour after posting, I got response from someone. The sender showed as anonymous. I opened the message and the only text in it was 'SUCK ON THIS FUCKING SISSY!' I scrolled down and opened the attachment. There was a picture of a white male from his mid-section down to his knees. In the middle was a very large cock with veins pipping from it. It was hanging halfway down to his knees. My mouth dropped open and I instantly got hard was started drooling.

I didn't hesitate and replied with simply 'MY PLEASURE!' After messaging back and forth a few more times ensuring he wasn't someone that would beet another person up for being different, I gave him my address.

About 30 minutes later after I had freshened myself up, he arrived at my door. I opened the door and let him into my entry hallway. I asked if he would like a drink and he said whiskey on the rocks in the sexiest male voice I have ever heard. I poured him a glass with some ice and double shot of whiskey. As I came back to the hallway, he was not there, but his clothes were in a pile. I turned to walk back the other way down the hallway and found him standing at the end. Completely naked. His huge cock swaying back and forth getting hard right between my eyes. I walked up to him and gave him his drink.

As he drank his first gulp, he grabbed my head and pushed me to my knees and guided me to his giant erect cock. I grabbed on with one hand and noticed my fingers would not go all around it. He took a half step forward and forced the head through my drooling lips allowing me to savor his precum. As forceful as he was on pushing me down, he was still gentle in the way he took his time forcing his head in and out my mouth. I was savoring every inch of his large cock as it stretched my mouth open and further in.

After 5 minutes of him forcing his way in my mouth, I started bobbing my head on this beautiful shaft. I bobbed faster then slower looking up into his gorgeous blue eyes making sure I was getting his entire shaft wet even though I was only able to get four or five inches past his head in my mouth. There was no way I was going to get something that large into my throat, not for lack of trying.

For what felt like an hour (was only about 15 more minutes) I felt him starting to thrust harder and faster in my mouth. By this time, my jaw was starting to hurt. Thankfully he pulled out of my mouth and slapped my hands off his cock. He started stroking his own cock moaning very loudly. Expecting him to cum on my face or in my mouth, he pulled me up off my knees and started pouring cum onto my neck. I was amazed at how much he cam and the force it was coming out as his cum was splashing as he was giving me a pearl necklace. As it started running down my chest, I scooped a handful up and licked it off as I looked up at him. I think I made him cum more as he grabbed my head and forced his cock back to the hole it belongs in. He let out another grunt and filled my mouth up with another load of cum. I cannot tell you how wonderful his sweet salty juice tasted.

After I had licked all the cum of him, he helped me stand up and gave me a deep passion kiss. Not lasting long enough, he pulled away and lifted me up to carry me into the spare bedroom like I was his bride. He laid me on the bed on my back with my head near the edge. He knelt and continued to kiss me. Again, he pulled away from the kiss entirely too soon. What he replaced it with was his glorious cock. Pulling my arms, he moved me closer to the edge of the bed, so my head was just off. Doing this allowed him to drive his cock deeper into my mouth and opening my throat.

Once again, he started thrusting slowly to get used to this position. Once I was comfortable, he started thrusting deeper while his hands were on my cheeks controlling the position of my head. Once he felt I was ready, he started entering more. He didn't stop until I felt his balls on my forehead. He stayed in that position and told me to try to control my breathing. Once it was under control, he started pulling out a little and going back all the way in. This lasted until our breathing was in rhythm. Suddenly, he pulled all the way out making me lose my breath. As I caught my breath, he drove his cock call the way in. He did this about 4 or 5 times. I was becoming more comfortable with his large member entering and exiting my mouth and throat. As he was throat fucking me, my face was getting coated with all my saliva. I knew he had enough lubricant to keep going, which he did. He asked if it would be ok if he came deep in my throat. As my mouth was stuffed, all I could do was make some gurgling sound which I hope he indicated it as a yes. I was getting more acclimated to his cock with each stroke. As his heavy ball sack kept hitting my forehead, I thought I might have a bruise. As he started moaning, I felt his cock pulsing in my mouth, and he shoved it in farther than he had before. He started coming and I'm sure I felt his hot seed spurting into my tummy. This was all a first-time experience, and I was wonderful.

After he was done cumming and pulled out of my mouth, he asked if I was ok. I tilted my head back and kissed the head of his cock to indicate I was. As I was still in my dress, I asked if I could get his clothes for him. He responded by saying he wasn't done with me yet. I blushed. He asked where the bathroom was, so I pointed him down the hall. As he used the bathroom, I went and got his whiskey and refilled it for him and got myself a drink. I took our drinks to the spare bedroom and sat at a table where there are two chairs. He came from the bathroom and takes a seat across from my next to his drink. After taking a drink, we chat for a while getting to know each other better, which is something I normally don't do. After about a half hour, I excused myself to go clean myself up and change.

I went to my bedroom, took all my clothes off and washed my neck and chest where he had cum on me. I then cleaned my face and reapplied my makeup. My wig was ok. Going back into my bedroom, I choose a white teddy, with matching G-sting, garter belt and white stockings. I readjusted my cock as I had it tucked up with tape looking like a real vagina. I put on my white sandals with 5" heel and went back to the spare room.

As I walked in, I noticed his drink was empty again so offered to refill it. He said please, so I did. When I came back, he was lying on the bed, naked of course, and motioned for me to come lay with him. As I laid on the bed, he grabbed me and held him tight to him kissing me deeply and passionately.

This time, I was the one who broke the kiss. I told him to lay on his back and I crawled on top and straddled him. I instantly felt his cock getting hard, so I started gyrating on top of it and stroking it between my thighs. He asked me if I was enjoying myself and I just batted my eyelashes at him. I then asked what else he had in mind doing to me. He answered back by asking what I want him to do. I responded by giving him a kiss on the cheek and whispering in his ear that I wanted to fuck his cock.

As I reached over to the night table, he reached down and started removing my G-string. Once they were off me, he turned me around and started kissing and licking my boi pussy. I started applying a generous amount of lube to his cock as his. He then grabbed me, turned me around to face him and raised his lubed cock to my hole. I braced myself as he held is cock at my entrance. He slowly started pushing in. my sphincter opened and I happily took the head of his cock in with a little amount of pain. He stopped there waiting for me to catch my breath. Once I had my breath back, I briefly kissed him deeply then sat back so his cock entered me more. I slowly rocked up and down on his cock for a bit. I know it was not all the way in and doubted I could get it all the way in, but I tried to get as much in as I could for maximum penetration. He started thrusting in and out to match my thrusts with each trust going just a bit deeper the whole time I was moaning and screaming out as the little sissy slut I have always wanted to be.

I needed to rest my legs for a minute, so I just sat back with him inside me. I felt both pain and unbelievable pleasure as his cock entered me completely. I laid all the way back screaming from pleasure as he sat up at the same time. He wrapped my legs around his back, grabbed my arms to hold by body against his and stood up with his cock impaled in me. What I didn't expect was what to come. He walked towards the wall, put my back up to it and roughly fucked my pussy for all it was worth. I could feel the head of is cock filling every inch of my rectum not leaving anything untouched. I thought I was in extasy sitting on his cock, this was a whole new level of pleasure. Without physically cumming, I had multiple orgasms. I was Jell-o in his hands. He kept fucking me till I almost blacked out. At about the same time, I felt every vein in his cock when he started pumping stream after stream deep into me. He kept pumping and thrusting until my ass was full and cum was spurting out. He came so much and so forceful I could swear I tasted it. I had no idea anyone could have this much cum in them.

When he was done, he pulled out dripping and let me down on the bed gently. I grabbed his cock with one hand and pulled him towards me. I took him in my mouth and started to suck and lick our love juices off to clean him up. I knew my entire but was a mess and dripping with cum, so I reached back, took a handful and gobbled it down. Again, this was something new to me and have never done. I could tell he was turned on because he got instantly hard in my had again.

I laid back on the bed and raised my legs, grabbed his cock then guided into my dripping hole. He took this as a hint and started fucking me hard. I thought he fucked me hard last time, but this time was so much more so. Even though I was well lubed, his cock I was still feeling all its girth and friction. I did however orgasm a few more times before he was done, which only took about 5 minutes. As he really started grunting indicating he was about to cum, I looked up and told him I want him to cum on my face. When he pulled out of me, we both heard a 'pop' which felt funny, and we both giggled. I was still giggling when I felt the first splash of his hot man juice right between my yes, then another and another and another until he was finally done. I had so much cum on my face, I was breathing it into my nose while I was licking my lips. I didn't care for it stinging my eyes though.

After we had cleaned up, I changed the sheets on the bed, and we talked for a while longer. I asked if he wanted to sleep here, but he declined saying he had better get going. I asked if we could see each other again to which he replied 'certainly'. He got dressed and I was in a white silk robe. I showed him to the door and planted a huge kiss on his wonderful lips. After I closed the door when he left, I retreated to my room to get ready for bed. It was then, that I realized we did not even get each other's names.

I really hope to be with him again...