The Bachelor Party

This is my first story attempt. I hope it's ok. I won't bore you all the details. I am dean, a mid 20 something college graduate. I stand 5'7 weigh 150 lbs, 6" cut nice cock. I have dark brown eyes, brown hair. My body is naturally very smooth. I do trim around my cock and sometimes even my arm pits as the appearance of hair to me, on me, seems unsightly. I have had my share of girlfriends though nothing long lasting and meaningful. Of course, I use the web to watch tons of porn to satisfy our human urges. Yes, some of that porn can be bisexual or trans related. What did I care? I knew I wasn't gay or even bi, but I couldn't deny those images got me very excited, especially seeing those sexy women in the colorful, revealing and sexy lingerie.....But let's get to the story...

I have been out of college a couple years when I received a wedding invitation from one of my old roommates, Dave. I was glad to hear from him, but hadn't really spoken to him much after college. As time got closer, I received a text from Dave, letting me know he was having his bachelor party in Vegas and he would love if I could make it to catch up and all. As luck would have it, I would be there for a software show and told him I could stop by to say hello.

He replied and told me that him, a couple of his roommates and work buddies would be there along with his dad. I should tell you that Dave was a good looking guy, dark hair, blue eyes, chiseled, you get the picture. His friends and him all could have starred on a high school football team. Dave's dad stood a bit taller than Dave, maybe 6'2 and over 200lbs, thinning hair but from what I could recall was still in decent shape. Dave said he would text me the details as it got closer.

I landed in Vegas and headed to my hotel room. As I unpacked, I got a text from Dave telling me we would be meeting at a place called Guys and Dolls and then decide where to go from there. I told him I never heard of it but luckily it was close and I was able to walk to it.

As I got closer, I saw the usual stripper like neon sign showing what looked like a outline of a sexy girl in heels lifting her skirt. I haven't been to too many strip clubs and well I always feel a bit anxious in them since well, I'm not exactly a man's man. I took a deep breath and opened the dark doors, letting my eyes adjust I looked around. I saw the typical businessmen, locals and the sexily clad women strolling the floor and some serving drinks. A lot of the women seemed more statuesque, but I didn't think much of it. I saw Dave waving me over so I headed over to the table. Once there I found Dave, 3 of his buddies and his dad. All of them except Dave's dad, had a couple empty shot glasses in front of them. I was introduced to them. Two of Dave's friends were from college and 1 was from work. As I said, they all could have been stars on their high school football team, They all looked like they spent time in a gym.

Dave's dad stood up and smiled and said hello. I said, " hello Mr Jones", but he said to call him Steve, as we are all adults now.

Once seated and a drink and shot in front of me, I started looking around and noticed a lot of the women appeared, taller than most girls I've known and a bit on the muscular side, but still sexy and shapely. Dave leaned over to me and laughed.

Dave said "Dean, this club also has trans and crossdressing strippers. My friends thought it would be fun to start the night off with some levity. You don't mind do you?" I nodded my head and due to my nervousness I began drinking a bit faster than normal, not sure why I was feeling a bit uncomfortable.

The occasional stripper stopped by to ask if I wanted a dance and called me Honey. I couldn't help but feel my cock stir, but was always more self conscious about my body, so politely said, " no thank you".

As the night wore on and the beer and tequilla shots flowed, the lights went on and an announcer came on. "Ladies and gentlemen, it is that time of the night where we look for unsuspecting victims, I mean participants to participate in our amateur hour."

Needless to say I was feeling no pain, but I could feel myself sinking in my chair like in class when I didn't want to be called upon.

Well, as luck had it, my worst nightmare was realized. A cute petite girl strolled over to me and pulled up a chair. She had a cute pixie blonde hair cut and a cute pink string bikini with pink shiny heels that must have been 5" tall. Her name was Trixie and she pulled my arm as she sat closer and whispered in my ear.

I shook my head no, but by this time all the guys were yelling, at me, "What's going on?", they yelled.

It was then she told them "I've been watching this cute thing all night and love him to join me onstage and I think he could really win the $500 for the amateur contest."

As I kept saying no, Dave's buddies were all standing up yelling "Go for it!, go for it!" They told me "Don't be a poor sport, do it for your old college buddy Dave." Dave looked at me and smiled. "It could be fun", Dave said.

I looked at Dave's dad, Steve, who didn't seem interested, he had his eyes buried in some real estate magazine or something.

So, I reluctantly stood up. I looked around and saw about 3-4 other guys getting pulled up. Most seemed larger, rather bearish compared to me. There was one guy who was taller and fit, but he had what appeared to be a couple days of beard growth. I definitely was the smallest and least hairy. We all got pulled back stage. The other guys seemed to congregate together, while Trixie pulled me toward the back where is was more quiet and secluded.

Trixie then said "Ok honey, let's lose those clothes and see what I have to work with". I got down to my underwear. Trixie then giggled and said, "Oh shy are we?" She then gave me a pair of pink lace panties and told me, "You, can go behind the screen and put them on shy baby" and smiled.

They looked like bikini's but a thong in back. I admit they were sexy and as I pulled them up I felt my cock stir. Before I came around from the screen, I tried to get my cock to go down.

I stepped out, Trixie smiled and said, "Oh my, aren't you a sexy thang!" I couldn't help but crack a smile and say, Thank you."

For the next 15 minutes Trixie did my makeup, added perfume, and then got a short pixie wig similar to hers except mine was more of a dirty reddish color. When I looked in the mirror I could not believe it. I was looking at a cute little girl. I felt attracted to the woman I was looking at. I got this weird feeling in my stomach and again felt my cock stir.

As Trixie worked on me, i could hear the announcer introduce the other guys. Calling them names derived from their guy names, Thomasina, Stephanie, etc. I could hear the hoot and hollering and laughing as if some big joke. This made me feel a lot better thinking this was all in good fun and no one would ever think, well you know.

As Trixie finished, she said, "Ok, let's get that outfit that will win you that $500!" She rummaged through a rack and pulled out a cute pink fishnet body stocking, matching the panties I was now wearing. She then grabbed a pink fur collar and a hair band with pink cat like ears.

Trixie came over, "Stand up honey, let's get a good look at you!". I stood up, Trixie kneeled and slipped on pink matching heels, then rose to add the fur collar and ears. I looked at myself in the mirror I remembered those sexy trans and sissies I watched on the web and thought I looked a lot like them. I again felt my cock stir.

I then heard heard the announcer. "And for our last contestant, please welcome......Miss deanna, the persian pink kitty!" I broke out of my trance and Trixie grabbed my arm and said' Ok honey, it's show time, go win that money!"

I stepped to the entrance and the stage was black, the crowd silent. As I stepped out, Michael Jackson's PYT started playing. I walked out and a spotlight hit me. It seemed as if the crowd saw a celebrity and a hush came over the crowd. Everyone was staring. I paused, then someone hooted, then another.

I could hear Trixie encourage me, yelling to me, "If you want the $500, you have to work it baby girl!"

I started to walk, foot over foot, trying not to stumble. This accentuated my hips and I placed a hand on one swaying my hips. Guys started coming to the runway, throwing dollars at my feet. I started smiling, blowing kisses, not sure what was coming over me. As I got to the runway closer to our table I saw Dave's buddies all standing, hooting and hollering. Dave was more subdue and only smiled and gave me a thumbs up. When I looked at Mr Jones, he looked up over his magazine, paused, smiled and, oh my god, did he wink at me? I think he did!! Then went back to his magazine.

As I left the stage my heart was pounding, the adrenaline was rushing, I could barely catch my breath. As I got back stage Trixie greeted me with a hug, I could feel her bulge on my thigh which excited me. She kissed my cheek and said I did great. She led me back to the changing table where I was stopped dead in my tracks. There on the floor were all my clothes in a plastic bag and soaked. I picked it up and immediately smelled the beer that had spilled and coated all my clothes. I practically started crying.

Trixie was very apologetic, "OMG I'm so sorry, it must have happened when you were on stage". The manager came by and gave me $1000. He said, "Here darling, you won the contest and here's another $500 to pay for your clothes." He then offered a long overcoat to wear and cover up.

I was in tears as I walked out to our table, the men still hooting and hollering. I approached the table.

Dave stood up, he said "dean what happened?". I told him about the accident, the beer and my clothes. His friends, now drunk and acting like asses all said "hey baby, we can take you home". I just gave them a STFU look.

Mr Jones then stood up and said, "Well dean, I can take you back to your hotel where you can change and then rejoin the guys. I think It's time for me to turn in anyway, I can't hang with you young guys". I reluctantly agreed with Mr Jones, I wasn't looking forward to walking back to the hotel dressed like this alone.

As we left, several men were all saying, "Goodbye Miss deanna, Ms Kitty, hope to see you again". That actually made me feel good and I smiled and waved back as I clutched the rain coat trying to remain covered.

Outside, on the pavement we walked slowly. Mr Jones understanding the newness of heels on my feet, walked slowly along side me. Occasionally he would place his hand on the small of my back steadying me, lingering for a bit. It felt weird, but actually for some reason sent a different kind of feeling through me. We made small talk about college and what I was doing after. The fact that I wasn't dating anyone and not close to getting married.

We made it to my hotel and I told him, "Thank you Mr Jones, it was nice of you to walk me back, but I think I can manage from here."

Mr Jones replied, "Nonsense, I came this far, I want to make sure you make it to your room safe and sound". I smiled and agreed. We got to my door and I fished out my room key from my beer soaked jeans. That is when I turned to Mr Jones and said "you've been so nice, would you want a beer before you leave?" He smiled and said "sure, why not, as long as it's no bother".

As I opened my room door I felt Mr Jones close behind me, almost feeling his breath on my neck. the room was cool and dark. the curtains open with the neon lights from the strip showing through. I walked in and felt Mr Jones hand's on my shoulders removing my coat..."here let me help you with that" he said. For a second I thought I felt his fingers linger on my shoulders. For some reason I felt naked in front of him, I walked to the mini fridge and bent down. Mr Jones had made his way over to the large window. As i stood I caught him looking at me as I bent over. I walked over and handed him a beer he opened it and handed it to me, then took the one from my hand. He stepped back and said "beautiful view you have here", he moved such that he was behind me and I was staring out the window. "Yes it is" I replied.

It was then it happened. I felt Mr Jones hands on my hips, gripping me firmly. His lips close to my neck and ear, breathing warmly, his bulge gently toying rubbing my bare ass. I stood frozen. He then whisperered...."deanna, you do look so very sexy tonight....did you enjoy yourself tonight young lady" As he did this, his hands moved up my stomach to my chest and began fondling my nipples. His breath on my neck.. "Did you like all those men wanting you darling?" He pressed firmer, I could feel his feet inside mine. moving my legs apart. He kissed my neck and I felt myself tilt my head stretching exposing my nape to him. I finally confessed, "yes Mr Jones yes, it felt amazing!" He then said, "baby, call me daddy, you are now my baby girl" his hands traveled to my thighs groping them kneading them as i felt his bulge press between my cheeks. His hands massaged my inner thighs near my clitty and he felt how stiff i had become. then i felt his hand slide up my asscrack, splitting my cheeks, his fingers started rubbing my hole. He bit my ear, asking me "do you like that baby girl, purr for me my kitten, you like daddys fingers there don't you?" All I could do was place my hands on the window for balance and stick my hips out, not sure what was coming over me I moaned, "yes daddy, yes, it feels amazing, please don't stop".

With that he stopped like a father taking away a new toy he walked to the bed and began undressing. he dropped all his clothes on the floor and went and laid on the bed. It was then i turned and saw his masculine hairy 6'2 body and what looked like a very thick 7" cut cock. I felt empty, wanting, was this his plan, to tease me into wanting it? if so it was working. He patted the bed, "come here baby girl, show daddy what a good kitty you are". and with that I crawled up, he spread his massive thighs that allowed me to crawl between them.

I couldn't help but stare, I licked my lips and gulped as he swirled a finger on his head gathering clear precum. "here baby, come have a taste". I moved closer and felt his finger rub my lips then push in. My lips parted instinctively, tasting the precum mixing with my saliva he held his finger in and smiled. as he pulled it out i leaned forward. "oh my baby girl is hungry" he smiled and gathered some more and again inserted his finger feeding spoon feeding his new baby.

He then moved his hand to his cock and said, "go on baby, taste for yourself". I slowly crawled closer and moved my mouth to the head. I let my tongue out and licked the soft velvety head. tasting precum I licked again gathering more I could taste. I heard Mr Jones, daddy, moan and that made me feel good for some reason. I licked more and more then i opened my mouth and took his head in. "that's it baby girl, that's it, suck daddys cock, you know you want to, you know you need to, enjoy daddys cock" with that something triggered and i started rubbing his cock and balls and trying to get more and more into my mouth. With every one of his moans felt like encouragement. I sucked and sucked. I could feel his big balls fill, tense up, get full. I felt his shaft expand, thicken, he head become wider in my mouth. When I thought hw was about to cum. He stopped me.

He sat up, told me to get on all 4s..."damn baby, daddy needs to taste some of that pussy" the way he sounded was a bit more voracious, more aggressive and before I knew it he was behind me pulling my little smooth cheeks apart and lapping me like a hungry dog. I have to admit it felt incredible, my clitty stiffened. I could hear myself moan as daddys tongue ventured in my little hole. he smacked my ass and told me how sexy a girl I was and that he knew i needed it as much as he did. he then started pressing his head against my ass.. I didn't know what to do..i wasn't sure about anal but the feeling was overwhelming. he then brought a bottle to my nose and told me to "inhale baby girl" as I did I felt him push in. it hurt like hell but once in he stopped and paused. he rubbed my back n ass n shoulders.. "ohh baby girl, you are what a daddy wants and needs, we will have plenty of good times" he then brought the bottle up and feeling light headed i inhaled deep again. with that he pushed in and i yelped. he grabbed my hips and started thrusting slow and deliberate. I could feel his thickness stretch me, his bulbous head hitting every nerve ending in my ass. I started rocking back into him, he rubbed me smacked me.

"Ohh baby, daddys gonna cum...cum in your tight little pussy...you ready baby girl for daddys seed? all i could stammer was " yes yes yes daddy"

With that he shot his cum right into my virgin sissy ass.. afterwards we laid along side another, he stroked my hair, i stroked and sucked him, he sucked me and fucked me all night. needless to say it was the best bachelor party of my life.