This is a true story. Names have been changed or omitted for privacy reasons. As always, if you're underage or for any reason, not legally permitted to read such material, please do not continue.
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Copyright MCM 2008 All Rights Reserved
We all make mistakes...but sometimes things work out for the best. When I was 24, I moved back to Pittsburgh. I'd been living in a small, rural community in Ohio that was possibly the most boring place on Earth.
Being a musician, I figured the best way to get my name around town & start getting gigs was to start hitting the jam sessions held all over the city, of which there were plenty at the time. For those unfamiliar with the scene, at a jam session, you basically just show up with your instrument and sometimes put your name on a sign-in sheet, sometimes you're just asked to sit in. As I had a "look" back then, I never had to sign in. The other musicians just knew I was a player! It was the early 90s and instead of the typical long, dirty hair look, I sported an exaggerated pompadour and usually wore a bowling-type shirt or a guyaberra and usually baggy dress pants. I stand about 5'8 but was well built...broad shoulders, well defined chest and a 32" waist.
After a few weeks, I'd gotten to know a lot of the regulars at the jams. One guy in particular & I really hit it off. He was a blues guy and a helluva musician. He always came by himself but would often brag about his wife. He'd said she was a model and if the photos he'd shown me were any indication, a good one! She was slender, with long, thick blonde hair, blue eyes and a killer body. I often asked why she never came along and his answer was always something along the lines of "I couldn't trust you guys around her!". I had to wonder what was up. Was she cheating on him?
Anyway, I started playing with a band on a regular basis and this guy would sometimes sit in with us. One night, he finally brought hiswife, Monica, with him. She was even more beautiful than her photos. And dressed to the nines! On a break, he introduced me to her. I took a seat at their table and the conversation and drinks just flowed. She seemed to hang on every word I spoke. She kept moving closer & closer to me. I have to admit, I was a little uncomfortable as I'm not one to try to cheat. I just figured that I must have been imagining what I perceived to be her attention.
A few weeks later, I received a call from my musician friend. He & his wife were having a party for her 26th birthday and wanted to invite me. As I was still relatively new in town, I thought it would be fun so I made plans to go. I picked up a bottle of wine and a card and got to their house about 9:00pm. There were loads of people including some other musicians I knew. When Monica saw me, she came up to me & threw her arms around me and gave me a kiss. I thought this was a bit forward but maybe she's just the `huggy-kissy' type. I gave her the bottle of wine & card. She accepted them graciously then set them on a nearby table. She then turned back towards me and put her arms around me again, giving me this sly look. Wait...is she grinding her crotch into me? No. Can't be. Maybe she's just got a buzz on. Trying to get myself out of my friend's wife's embrace, I commented on how nice the house looked. She took me by the hand and said she'd show me around and introduce me to the other party guests.
Theirs was a small house; just 2 small rooms, kitchen, bath, bedroom and basement. She made sure to show me all of them...all the while never letting go of my hand. She made sure to show me the bedroom last. She stood between me and the doorway and started to comment on how nice I looked in tight jeans...and how my jeans would look better on her bedroom floor! WTF I thought! I tried to laugh it off...hoping that this hot woman, my friend's wife, was only joking. Using the only excuse I could think of, I asked to use the bathroom.
When I came out of the bathroom, she was waiting for me. Uncomfortable doesn't even begin to describe the way I was feeling! Here was this hot woman, practically throwing herself at me and ignoring her party guests and her husband! She said she wanted to introduce me to someone. She took me into their den and there stood a young transvestite -- "Vicky". I could tell that Vicky was a transvestite and looked to not be older than 19; wearing a short, tight print dress, 3" black heels, a long blonde wig and a bit too much make up. What I haven't mentioned thus far is that I really like transvestites & transsexuals. How did Monica know this about me? She couldn't have! Aside from a few close friends in Ohio, I'd never told anyone! Monica then whispers in my ear, "I have the feeling you'll be getting lucky tonight...with at least one of us."
Did I mention that by this point, I was becoming very uncomfortable? I was torn between my morals and not wanting to accept my friend's wife's flirting and my desire to fuck this young transvestite and my desire to keep my private life private and NOT share it with everyone at the party. This was looking to be a loooooong night. Needless to say, I was fighting a raging hard on.
As luck would have it, my friend needed to go on a beer run and asked if I'd go with him to lend him a hand. WHEW!!!!!! My way out! I more than readily agreed to go with him and I excused myself from Monica & Vicky's company. As my friend and I were driving to the store, he was laughing about how much Monica always talks about me. He told me that ever since the night she met me, I was all she talked about. "What a nice guy" and "what a talented musician" and "he's so funny". This was not making me feel anymore comfortable. I just tried to laugh it off and change the subject...but the thoughts of getting it on with Monica or Vicky kept creeping into my head. I couldn't let myself do anything with my friend's wife, but Vicky was a whole other matter. I decided that when we returned to the party, I would try to get some time alone with Vicky.
Upon returning to the party, Monica was waiting outside for what I assumed was "us". I was wrong. She only wanted to talk to me. She told her husband to take the beer in and she took me by the arm. She then whispered in my ear, "I've been having naughty thoughts about you since we met and I really want to fuck you". That was not what I needed to hear! I hurried and excused myself to help my friend load the beer in the house. He asked if I could put a few cases down in the basement. I decided to see if I could get Vicky's attention at this point. Could be a good excuse to spend at least a few minutes alone talking. I caught her eye and suggested she meet me in the basement...and asked if she could bring a couple cold beers.
Vicky followed me to the basement. I thought I'd just get to the point and I told her about Monica saying that I'd be getting lucky with at least one of them. She smiled and gave me a sly look and said that I probably would...but she wasn't THAT easy! I laughed and apologized for coming across like an idiot. She told me she thought I was cute...and that most likely, I would be getting lucky before we went back upstairs. I decided to be bold and took her in my arms and kissed her. She returned the embrace as well as the kisses. Soon, her lips parted and our tongues were entwined. I was harder than Chinese algebra at this point! I want her soooooo badly! As we embraced, I know she could feel my dick throbbing against her. I could feel "hers" too! I was soooooo turned on! Vicky started to stroke me through my jeans and I thought I would just explode! She slowly pushed me against the wall and worked her way down to my crotch. She slowly unbuckled my belt, unbuttoned my jeans and pulled down my zipper. I was going commando (no underwear) and my 6.5" cock burst out of my pants. Vicky looked up at me with the sweetest smile and took my cock in her hand and slowly started to stroke it. I was in heaven. I went to touch her face and she backed off a bit, giving me a "no no" look. She then started to kiss the head of my cock, slowly kissing along the bottom of my shaft as she raised it up with her hand. She started to kiss my balls...I thought I was going to pass out if I didn't cum soon...but Vicky wasn't about to let that happen! She took me in her mouth and started to slowly work up and down my shaft. She held my balls in one hand and would occasionally squeeze them hard...just enough to hurt to where I wouldn't cum yet. She used her other hand to start feeling the crack of my ass. I was losing my mind! She started to probe my crack and was still going down on me at the same time. Her nose was into my pubes when I just couldn't hold back any more. I told her I was about to cum...just as I did, Monica came down into the basement and caught us!
"Naughty naughty!", Monica giggled. "I told you he'd be into trannies", Monica said to Vicky, who was licking my now softening cock. I blushed. What else could I do? Monica then came over & asked if she was going to get her turn. Before I could explain that she wouldn't, due to being my friend's wife, my friend came downstairs, wondering where we all were. I felt so bad...he walks downstairs and sees Vicky on her knees in front of me, me zipping up my pants & his wife asking for her turn...I'm surprised he didn't shoot me! The look on his face told me his wife had put him through this before.
It was getting late and the party was breaking up, and as our private basement party was also broken up, I said my good nights and thanked my guests and went on home. Vicky had disappeared and I didn't get a chance to say good night. Monica said she'd give me her number but never did. I was to find out that she wanted me to herself.
I saw my friend later on that week. I tried to tell him what had really happened in the basement (minus the part about Monica asking for her turn). He just laughed and said that his wife can be a bit "goofy" when she drinks. He was apologizing to ME for HER behaviour! He teased me a bit about "getting sucked off by a guy in a dress" but also said that his wife had lots of "friends like that". He suggested that I come over sometime to show him some guitar stuff. I was just glad that everything was cool. Our friendship was good and Monica started seeming more like just his wife and wasn't trying to molest me (for a while). She would often call me and ask if I could grab her things from the grocery store as her husband often worked late and she didn't drive. I wasn't thrilled about this but being a friend, would try to help when I could.
One night, I ran into Monica and her husband at a club. She was looking HOT in a short, tight dress, heels and fishnets. She was giving me that look again. Her husband suggested we all go for breakfast after the club closed. I really didn't want to but they both talked me into it. I just didn't want Monica sitting next to me. I knew by the look in her eye, she'd probably spend the whole time with her hand in my crotch. Monica & her husband sat on one side of the booth & I sat on the other. It wasn't 5 minutes before I felt her foot playing with my leg. I tried to move a bit without being obvious but she kept at it. At one point her husband went to the bathroom...her foot went straight for my crotch and my now bulging hard on. She was rubbing my cock with her foot and telling me that she wanted to suck my cock under the table. She wondered out loud what her husband would say. I was, needless to say, speechless.
After I'd been at my job for a few months, I put a down payment on a new convertible. I loved that car! My friend called one day & said he'd told his wife about it and she wanted to know if I would take her for a ride. I made sure he was ok with me taking her for a ride & I agreed to pick her up for lunch that Friday as their house wasn't far from my office. That Friday was a beautiful day. Sunny, warm...perfect day for riding in a convertible. I picked Monica up and we just drove around for a while until we found a place to grab a quick bite. We had a really nice time. As I was driving her home (I had to get back to work) she as usual turned the conversation towards her attraction to me. I was stuck. Here we were, in my car, a few miles from her house and I'd just have to be polite. She simply explained that she wanted me and WOULD have me. I tried to explain that I wasn't in the habit of sleeping with my friends wives...or any other married women. She then asked how long I'd liked trannies. I just blushed & didn't answer. She then asked if a tranny had ever given me a handjob while I was driving. She then reached over and started stroking my crotch. I was hard immediately. I tried to ask her to stop but before I could Monica asked, "You did know didn't you? You did know I'm transsexual?" Again I was speechless. Worse still, I was now even more attracted than before! "What about your husband?, I asked, as if it really mattered at that point. "He's an asshole & I hate him" she told me. I tried to concentrate on my driving but with this hot tranny stroking my cock, I almost wrecked a few times. She wouldn't let me cum either. She said that it was hers now to do what she pleased with. I hurried and got her home and before she got out of the car, I told her that we shouldn't be doing stuff like that. "Don't be silly", Monica said to me, "You're mine now."
(to be continued)