My Little Adventure

Let me start by saying that I have been crossdressing for over 20 years and I didn't really feel like a lady until just last week. I should rewind about 3 weeks so that I can explain what happened leading up to my little adventure.

I frequently shop at several local lingerie stores and adult boutiques. Three weeks ago I went into one of my favorites. A nice little lingerie/adult novelty store named Pricillas, which has several locations in Michigan. I have gotten to know the store manager; a lovely lady named Sherri Steiner. I have bought tons of outfits from her over the last couple of years and I am one of her best customers. She is always pleasant and very helpful. Not only does she not have a problem with me trying on outfits, most of the time she actually helps me pick out outfits that would look good on me and even gives me a female opinion of the ones that I try on. I have shopped there both in male clothing and in drag.

One day Sherri out of the blue, asked me if I have ever dated a guy while dressed in femine clothing. I told her that I hadn't but that I had thought about what it would be like to be with a man while dressed as a woman. I have often wondered what it would feel like to be treated as a lady for an entire evening. She smiled and asked if I ever had a 3-some. I told her "no" and she smiled widened. She asked if I would be interested in having a 3-some with her and her boyfriend Joe. I was floored at her bluntness. She confided that Joe has been begging her to bring another girl into the bedroom. Sherri said that she was afraid to because she was afraid that she would lose Joe to the other girl if she pleased him more. She spilled her guts to me as I stood there listening. I couldn't believe my ears. She was actually worried about losing her man to another woman so she wanted a crossdresser like me to pose as a woman and help her fulfill his (and hers too) fantasy. I couldn't believe that such a gorgeous lady could possibly lose any man that she desired.

I told her that I would think about it and let her know soon. I did have one condition; I wanted to see a photo of her boyfriend, Joe naked so that I could see if I found him attractive and what he had to offer. She agreed to take the photo as long as she could take one of me dressed in drag to show Joe. I agreed and we agreed to meet the following week.

I showed up half expecting her to say that she was joking, until she handed me the photo with Joe naked and much to my surprise, Sherri standing next to him naked also hold his nice erect cock. She asked me what I thought and all I could say was "Yes" She smiled and asked me to stand by the wall so that she could take my picture for Joe. I decided to be alittle naughty and remove my blouse and raise my skirt just enough to show my ass cheek as I looked over my shoulder in a seductive pose. Sherri snapped the pic and said that Joe would love it. She asked me to call her the next day and she what Joe thought of the photo and if he agreed to continue.

I called her the next afternoon and she was so excited that she could hardly concentrate on work. We agreed to meet at a motel on the outskirts of town in two weeks. I told her that I needed to find something special to wear for the occasion and she said that she had the perfect outfit and not to worry. She wouldn't tell me what outfit that she had in mind and I tried everything I could think of to pry it out of her. I used a last ditch effort by saying that I would need to try it on beforehand to make sure that it would fit. She laughed and said that by now she knew my size and body almost as well as I did. (This was true) I was on pins and needles for the entire two weeks.

On the morning of the big day I received a call from Sherri telling me that she would be over shortly to help me to prepare for the big evening. I waited for what seem like hours for her to show up. When she arrived she was carrying several large bags. I let her in and we ran to my master bedroom to prepare. She told me to run a bath and to shave extra close for a wild night of fun. I jumped into the bath and soaked for awhile before shaving and rinsing off. Before I was finished in the bath Sherri came in and asked me how far I wanted to take it this evening. I said as far as it goes. She smiled and handed me an enema bag and a scented douche.

I filled the enema bag with warm water and started the process of cleaning myself out followed by the scented douche. Once I was finished I walked into the bedroom completely naked and as smooth as a baby's backside. Sherri just smiled, as this was the first time that she had actually seen me naked. She had laid out on the bed a beautiful black leather corset with a matching leather panty. There were also black sheer nylons as well as a leather garterbelt. She also had a black leather mini skirt and white blouse. This was topped by a leather vest. I almost came right then. Sherri helped me into the corset followed by the garterbelt and nylons. When she went to pull the panties into position, that's when we had a real problem. My raging erection was not willing to be concealed. First we tried cold water but that didn't work. Sherri finally dropped to her knees and started sucking me to my first orgasm of the day. Once the swelling went down she pulled my cock back between my cheeks and pulled the panties into place. She finished helping me get ready before applying my make-up and wig. When I stood on the 5" black stilettos I was now well over 6 feet tall. I looked into the mirror and didn't even recognize myself. I was totally hot!!! Sherri got herself ready and we were off to meet her boyfriend Joe for drinks.

We drank and danced for several hours before we ventured to the motel. Once in the room Sherri was all over me. Kissing me, fondling me and totally arousing me in every way. Joe sat back and watched for a minute before he undid his pants and dropped them to the floor. That told us girls that it was now his turn for the attention. Sherri led me over to where Joe was now standing with his beautiful manhood hanging. Sherri told me to go ahead that she wanted to watch me pleasure her man first. I slowly reached out and grasped his semi-hard erection. I could feel its warmth and could feel his pulse beating through his cock. I stroked in for a moment before slowly leaning forward and letting its head pass between my lips. I swirled my tongue around its head a couple of times before I released it from my mouth and began bathing his cock with my tongue and saliva. He moaned with every pass and swirl of my tongue. Once I was satisfied that he was sufficiently bathed I once again took the now purple head back into my mouth and started sucking on it.

Before long I had managed to swallow half of his six inches before it started hitting the back of my throat. I stopped long enough to relax and start breathing entirely through my nose. I continued my journey down his erection with a certain goal in mind. I wanted it all and I was determined to make it happen. I was in ecstasy when I felt his pubic hairs tickling my nose and my tongue touched his balls again. I looked up into his face and smiled at him. Not that he noticed with his eyes closed. I slowly started my way back up to the head again before plunging back down again. Seconds later I could feel his hands grab the sides of my wig and start forcing my mouth back down again and again. I was soon slurping at a fevered pace as I felt his cock start to pulse and swell even more. He announced that he was about to cum and I increased my attention until I received what I had been waiting for.

He started spurting into my mouth and it felt like a dam had broken as wave after wave of cum hit the back of my throat. I tried my best to swallow it all but some did dribble out of my mouth and down my chin. Not bad for my first time. I continued sucking and licking his cock until it finally returned to its depleted size. I once again looked up at him and this time he smiled back. I was now in heaven and TOTALLY hooked on sucking cock.

Sherri walked over and planted a kiss on my lips and announced that it was her turn while Joe recovered. She was now all but naked and lay on the bed. She quickly spread her legs and invited me to eat her pussy. I gladly dove into her wet snatch. I ate her pussy for all I was worth. She had several small orgasms before she had me move into the 69 position where she pulled my now once again erect cock out and started sucking it out of Joe's line of sight. I couldn't hold out very long before I was filling her mouth again with my second load of the day. That triggered the most intense orgasm that I have ever seen a woman have. She squirted or should I say sprayed her juices into my mouth almost as strongly as Joe's orgasm had.

Good story but needs to be expanded. I've been a cock freak since a very early age. tasting a cock and taking the load of cum down your throat is fantastic. For the past three years I've been into crossdressing and living as a CD whore, working ABS locations, parks, and anywhere else that i can find some nice meat to fill my cunt. I spend most days and nights getting used by hard cocks in anyway possible .I love it.

So did Joe find out that he was being sucked off by a guy ? Can hardly wait for more.

Looking forward to the next chapter/ I'm sure hoping it involves you getting it in that cute ass and filling you up with hot cum.

you lucky guy...would give anything to have that happen to me