I Had My First Time With A Man, As A Crossdresser!!!

I had fantasized about being with a man for years... And it actually happened last week!!!! It was one of the most amazing experiences of my entire life. I was extremely nervous before hand but once things started happening, i just rode the ride.

It was a lte thursday evening and I was home alone. I was having a few drinks and started to get a little horny. So, i hopped on CL... I made a post as a crossdresser looking for a man and within 30 minutes I had 5-7 emails. So i went through the emails for close to an hour before I read one and saw a picture that gave me a good vibe. The man will remain nameless. Im very discreet.

Anyways, This gentlemen was staying in a hotel about 20 minutes away from my house. I thought it was going to just be a hook up and thats that. Little did I know what this night was going to bring me.

Im 6 ft. tall and 165 lbs. Im athletic and have very femanine curves to my body. I also have long brown hair to about shoulder length and im shaved smoothe. I began the night by taking a shower and only washing my body with womens soap products. Once I was totally dried off, I put on a black pair of lace thigh highs. Then, an A-Cup push up bra with silicone breast enhancer inserts. A B-Cup push up bra, A C-Cup push up bra, and then a bright blue corsette. My rack looked amazing! I put on the guarter belt and attached it to my thigh highs. Over that i slipped on a tiny white pair of brief panties. I hopped into a very small, flowy, grey skirt and tied on my white school girl top into a little bow right under my wonderful cleavage.

After I was all dressed I put on a diamond necklace, silver bracelet, and diamond earrings. I curled my hair and pinned it back, took my time doing my makeup, and topped it off with a fake pair of reading glasses. Igrabbed my purse and walked out the door with my high heels already constricting my feet.

My heart was pounding on the drive there. It was about 9 pm when arrived at the address he gave me. It was an extremely nice hotel and his room was up on the top floor. I had NEVER been in public dressed before this happened. I got on the elevator and a few guys got on. They were chuckeling and laughing. I though they were laughing at me, so I turned around and they were watching a video on one of their cell phones.

I exited the elevator and proceeded down the hall way until I came to his room. My heart was pounding and I hesitated for a while before I knocked on the door. But I did... and he answered...

He told me how wonderful I looked and kissed me a slight peck on the lips. It kind of caught me off guard. He immediatly shoved me out the door and said he wanted to get cocktails in the loung... My heart dropped. I thought i could hide in the hotel room for the rest of the night. I told him i didnt want to go. He told me he would give me $200 if i went downstairs with him. I took a deep breathe and followed him down.

I had quite a few sisters growing up so the womanly manerisms I had totally down. Even a decent voice. We sat there sipping on a few drinks. We both had worked up a buzz and decided it was time to head back up to the room. We were both giggling and stumbling around.

He was an older, grey haired, wealthy looking business type. He sat down on his chair to take off his shoes. But he kept messing with his phone. A got comfy in a chair and set my purse on the table. He asked if I was ready to have some real fun? I replied and said, most definitely. He laughed to himself and said, Good in a very strange manor.

About ten minutes had gone by and there was a knock on the door. Another business type man had entered the room. The two men shook hands and both walked into the suite and sat down. He introduced us, we shook hands and then there was another knock on the door. This was yet another business type man. But he walked into the room with this giant black bag. They all shook hands and then I was introduced to this man as well. At this point i had started to get very nervous...

I was digging for my cigarettes when the man with the black bag offered me a drink. I took it. I found my smokes and lit one up while I sipped on my cocktail. The men put music on and something came over me I just started feeling amazing and started dancing. They added something to my drink. Little did they know i was familiar with this "Spike" and handled it just fine.

They circled me sitting in chairs when I started dancing. One of the men waved me over to him. So i strutted over and gave him a lap dance. After a few minutes he sat me in his lap. The other men were watching... He grabbed my facing and started making out with me. I was super messed up but I totally went with it...

While we were kissing one of the men approached me from behind and grabbed my wrist, jerked me off the other mans lap. He pulled me close and started kissing me. I felt helpless but excited at the same time. Not before too long I was grabbed by my hair and pulled backwards, making out with the third guy behind me.

The guy infront of me pulled my skirt down while the other untied my shirt and ripped it off me. I was thrown onto the bed. Being in the highly euphoric state that i was, I layed on my back and giggled. One of the men, aggressively grabbed me by my legs and dragged me to the edge of the bed, Pulled my underware aside and starting fluttering his tongue on my a**. I leaned back again and just moaned.

Before i knew it all the men were naked and on the bed. They started feeling me up and kissing me as I layed there getting my a** eaten. I put both hands out to grab them. I started rubbing on both of them.

The man that was going down on me stood up and started digging through that black bag and pulled out a long strand of pink rope. They immediatly tied my ankles and feet together and layed on my stomach, in the bed. they were standing behind me and i could see anything. I was dragged by my hips to the edge of the bed. with my hands behind my back, my feet were tied up and i was now bent over the bed...

I heard the sound of wrappers... Then after a moment i felt one of the men reach under me and slide a condom on my pen**. I didnt understand why they put one on me... Then i started feeling wet fingers slide around my a**. Then one of those fingers made its way in... Then two... Then three... All i could do was lay there, wiggle, and moan. Then the fingers stopped. I knew what was next. I felt something VERY large putting preasure on me.

And in one big thrust he forced his way in me. I totally fealt something rip and I screamed. It slowly went in and out of me... Over and over. But I noticed something. It was really warm and i could feelit throbbbing. I was getting wetter. He wasnt wearing a condom and was pre ******* inside of me.

Then he slid out of me... He walked over and sat down in a chair and rubbed himself. I saw his massive piece and was for sure he was NOT wearing a condom. As i was watching him he told the other two he wasnt done and to bring me to him. They picked me up and untied my ankles, walking me over to the chair. I climbed in his lap facing him. I lean up over him, putting my chest in his face. He grabs my hips, guiding them, and then forces his way in me again as i gasp.

I put my arms behind his head. The other two come around and untie my hands. I kept riding him up and down, wiggling my hips. He moaned loudly and started kissing me. I fealt around and was able to find the other two d**ks. I started ******* them off. They both started to stand closer as i was getting drilled. They took turn in my mouth. They were going soo deep into my throat that I had tears running down my eyes... Along with my mascara.

They kept telling me to keep eye contact. They told me to get up. They put a pillow over the top of the back rest on the chair. They made me lean over it, tying my hands to the front legs and my ankles to the back legs. The man i was riding walked in front of me. I took him in my mouth... And in due time, i felt someone else enter me from behind.

The three men took turns on me in this position for another hour or so. Then one walked back over to the black bag... He pulled out a giant plastic sheet and put it under and around the chair i was tied to.

This is where things got out of hand. The man walked back to the bag and pulled out a clear plastic cup and roll of duct tape. I knew this couldnt be good...

One of the men walked behind me. I felt his hands grab my hips and he entered me again. But this time I was getting pounded. He started tensening up and getting loud. He let out a yell and I felt him throb hard and fast inside me. The followed by a wet warmth filling me up. These men were all going to *** in me. I was bent over and tied up. Helpless.

And thats what they did... one by one. I could feel it almost seeping out of me. Then the black bag opened again. it was some kind of garment with a hard slender device attached to it. The men held my hips down as the untied my ankles... They slipped this thing on me. Its was a thong. I felt something again slide inside me. It was a plug of some sort. The thing was holding it tight in place.

They tied the rope that was around my ankles to my neck... They took turns walking me around like a dog, ******* me and pulling me around. Every once in a while they would play with the plug in my a** bringing me emmense pleasure. They dragged me into the bathroom, made me lay on my back in the jacuzzi, and tied my hands above my head to the faucet.

They put duct tape over my mouth. The well hung man got in the tub and stood over me. He pointed his c**k at me and began to urinate. The other 2 followed suite. After I was totally drenched. They dragged me back to the chair, tied me up, and all 3 took turns busting inside me again.

At this point I was warn out. They put the plug back in and again untied me. This time they sat me in the chair. I was very slouched, my hands were behind my back an my ankles were again tied to the legs of the chair.

I could feel their ***** leaking out and running down my leg. They brought the cup over, placing it between my legs. Pulled the plug out and told me to push. ALot came out of me into the cup. At this point, they were taking turns sipping out of the cup, pulling off my duct tape and spitting it into my mouth. Making me keep it in there. Not spitting it out or swallowing it.

After it was all in... They started making out with me again. This large amount of *** was all over our faces. It was running down my cheeks, throat, and chest. They were also ******* me off as they were kissing me. And then finally I errupted in the condom. The most amazing ****** I have ever had in my life. I had p**s in my hair and *** all over my face and in my mouth.

They pulled the condom off me and emptied it into my mouth. The last thing I remember was them telling me to swallow... The next day I woke up in the hotel room alone. I was on the bed laying on my stomach. I was a mess. I fixed my makeup and went downstairs to my car. I had officially been used and abused... I really loved it!!!

GoSlowButDeep GoSlowButDeep
18-21, M
12 Responses Aug 26, 2012

I do not think I could walk after that! But Fantastic for you!

Wish my first time was this great, would love a bunch of daddies to make me their little sissy *****

If that was your first time, Ican hardly wait for the last, Darling

hoping for that when I get a man first time!!

Luck I wish this was me share some of the luck girl lol

add me please:)

naturall the hottest story ever. very jealous.

Still waiting for my first time, I would love it to be with a couple

Ohmygod. That sounds perfect.

What a real great insane time

What a PERFECT gurl!

That made me soooo hard!