Weekend Games

I was 42 and working at a dead end textile job. The only bright spot was that I worked with a woman named Tammy, she was a hot red head with a great body.

I figured I never had a legitimate chance of getting Tammy to go out with me but a guy could dream, or in my case it was more of a fantasy.

Tammy and I lived close to each other and one day she asked me if I could give her a ride home. of course I said yes. We worked 12 hour shifts at night, we worked from 7 P.M. to 7 A.M. 3 or 4 days a week.

Tammy was having car trouble and she started riding back and forth to work with me. I was getting to know her better and each day I was becoming more and more attracted to her.

It was the early '90's and not everyone had a computer yet. I lived alone and had no one to spend my money on so I had saved up enough money to buy a computer and a couple other gadgets.

No one knew my secret except for a few faceless "friends" on the Internet, friends I would never meet in public. My secret is that I was a closet cross dresser and I had been one since my early teens.

Living alone, I had built up a decent wardrobe, using the excuse I was buying things for my girlfriend which didn't exist.

One Saturday Morning we were driving home for work and Tammy was telling me about this new band she liked but she was not going to be able to buy the new CD until the next week.

I mentioned to her that maybe I could find it and download it for free from online. Tammy became all excited and started asking me all about computers and the Internet.

I dropped her off and went home to look for the CD that she was wanting, it was from a popular band so it was not hard to find and I easily downloaded it.

We were off for four days so I called her later that afternoon to tell her I had it and asked her if she wanted me to drop it off or wait until we worked again which would be on Wednesday evening.

She asked that since she had the use of her Mom's car could she come over and pick it up. How could I refuse? I spent the next two hours cleaning up the small house I was renting.

I knew nothing was going to happen between the two of us but I was hard all day thinking about the possibilities, it did not help that I was wearing a black set of lingerie, bra, panties, garter belt and stockings.

Tammy said that she would be over around 4 that afternoon. It was 2:45 and I had just finished cleaning the living room but was still dressed in my lingerie ensemble when Tammy knocked at my door.

I knew she could not see in and she had no idea how I was dressed. I told her to hold on a minute and ran to my bedroom to change. I did not want to keep Tammy waiting so instead of changing completely I kept the garter belt, stockings and black lace panties on under the sweat suit I was changing into.

I put on a pair of socks and tennis shoes. I know I should have been more careful and change everything but I figured that Tammy would not be there long and I would just change back later.

I let Tammy in. I wasn't sure if it was having Tammy in my house or the feel of wearing satin and lace panties but I was rock hard, not that Tammy would notice since my cock was so small, 5 inches at best when I was fully erect.

Tammy was a very tall sexy 26 year old. She stood 5'8", weighed 120 pounds, had long red hair and green eyes. Her smile was incredible but what always drew my attention was her breasts. I later learned that she wore a 36C size bra.

I was used to seeing her in jeans and a T-shirt at work but today she was wearing a tight white button up blouse that high lighted her breasts and you could see the edge of her lacy beige colored bra underneath. She was also dressed in a short gray skirt that showed off her pantyhose clad legs. She was wearing a pair of open toe sandals that showed off her toenails that were painted a bright pink.

I gave Tammy a quick tour of my house and we went into the computer room to retrieve the CD I had made for her. She started looking around the room and commented that I had a lot of tech gadgets and she especially liked my new digital camera.

When I gave her the CD she asked what she owed me. I laughed and told her that I only did favors like that for my friends and that I was happy I could do it for her.

She then asked if she could do anything to for me At first I had visions of her offering sexual favors but even though it was making my cock throb, I quickly dismissed that idea.

I laughed and picked up my digital camera and told her that I could always use a model. I snapped a quick picture or two.

She said that she did not think she was pretty enough to be a model but that she had posed for some erotic pictures for a former boyfriend and it excited her to pose.

I snapped a few more pictures of Tammy as I tried to think of what to say. I gulped as Tammy undid the first two buttons of her white blouse to show some nice cleavage, her breasts were perky and enticing.

I took a few more pictures and then asked her about the infamous Rolling Stones Tattoo that I had heard about. She said that it was on her right butt cheek and maybe at some point I would get to see it.

I was mesmerized by Tammy as she continued to unbutton her blouse and finally slip it off. I was getting several sexy shots of her creamy white breasts and hard nipples poking through the material of the bra.

She unbuttoned her skirt to show the top of her sexy black panties and as I started taking pictures again I was disappointed when she pulled her skirt back up and buttoned it.

She then told me about how her ex-boyfriend had shared the pictures of her with his friends when they broke up and that she needed some insurance that I would not show them to anybody or post them on the internet.

I promised her that whatever pictures I took would not be seen by anyone other than me. She said that I was a nice guy and that she felt she could trust me but that she wanted to make absolute sure that I would not share them before she would pose for more.

I asked her what I had to do to convince her that I would keep my word. Tammy took the camera from me and smiled. "I get to take some of you that you would not want shared and then I know you would not show anyone the pictures of me."

Now I was nervous when I asked her what kind of pictures that she want to take of me and she "ordered' me to undress. I made some stupid comment about no one wanting to see pictures on my fat body.

She got close to me and blew in my ear then said, that is the deal take it or leave it and that she bet I was looking forward to seeing more of her body. As she said it her right hand slipped into my sweat pants. My mind was in a fog and before I remembered what I was wearing and tried to stop Tammy she screamed "What the fuck are you wearing?" and Yanked her hand free.

I was blushing and about to pass out with humiliation. How could I be so stupid to let myself get caught like this..

I was still standing next to Tammy and before I could say anything she reached over and yanked my sweat pants down to reveal my garter belt, stockings, and panties.

I tried to cover up as she started snapping pictures of me. She slapped at my hands and told me to drop my hands by my side. After a few more pictures she ordered me to take off my sweat suit and I did.

She took several pictures, she even told me to turn around so she could take some of my sissy butt. Again I did as I was told.

She gave me a devilish and incredibly sexy smile as she held up the camera. I think I have all of the insurance I need. When I reached for the camera, Tammy slapped me hard across the face.

I gasped in shock, it was the first time I had ever been slapped and to my surprise I almost shot a load of cum into my panties. Tammy took a few more pictures then told me to show her my sissy cock.

I knew this had to stop and I tried to refuse but she slapped me again and held up the digital camera, "I have enough to humiliate you as it is, what is a few more pictures?"

I lowered my head in defeat and slowly lowered the panties i was wearing. Tammy was laughing so hard I thought she was going to lose her breath.

My face was burning from the slap and the embarrassment I was feeling. Tammy reached out to squeeze my small but hard cock.

She continued to humiliate me by saying that it was a cute LITTLE thing. She was running her hand up and down the shaft and I was on the verge of cumming.

Like I mentioned earlier I am a Heavyset guy and that just made my cock look even smaller. I am 5'10" 260 pounds with blonde hair and blue eyes. The extra weight gave me "man boobs". Tammy was stroking me with her right hand as she cupped my breasts.

"Nice tits do you have a matching bra to go with the black panties and stockings?"

I managed to mumble something as I shook my head yes. She continued to stroke me as she asked me all sorts of personal questions and I continued to answer them.

She had been stroking me for a couple of minutes when she asked me if I was gay. I told her no because I did not think I was, I had never done anything with another guy.

"You must be gay or I would have been able to make you cum by now. If you need to think about other guys cocks to get off you can. You can even imagine sucking big hard black cocks...."

She did not have to finish her comment because when she mentioned hard black cocks I shot my load all over Tammy's hand. She continued stroking my cock until there was no more cum leaking out of the tip.

When she was done milking my cock she raised her hand to my mouth and told me to lick. I was dazed from the incredible orgasm I had just experienced and without any resistance I started licking her hand clean tasting my own cum. I admit it was not the first time I had swallowed my own cum but it was very erotic to do it in front of Tammy as she took pictures .

When I was done licking the cum from her hand,Tammy ran her hand through my blonde hair. "I think you will make a cute girl. You may not be gay but by the way you reacted to the idea of big black cocks you have had fantasies involving black guys."

Tammy knew just what to say to keep humiliating me. "You have no reason to be embarrassed I think all girls want to try black at some point. I know I enjoy black cock from time to time."

Tammy slapped me again and told me to kneel. "You say that Andy is not gay but I wonder if Andie is a lesbian?"

I looked up at her with confusion. She was smiling down at me as she lifted her skirt and told me to lick her pussy through the pantyhose and panties.

Her panties were already soaked as I started licking her pussy. I reached up to peel the hose and panties down but she slapped my hand telling me to stop, that I did not deserve to see her pussy and that I was lucky that she even allowed me to taste her.

I licked her pussy until she had cum at least three times. She finally pushed my head away and told me to stop.

She ordered me to kiss her feet as a sign of respect. I kissed first one then the other. As I started to lick my way up her leg she kicked me away and fixed her clothes.

She told me to get her a beer. I got her one and brought it to her as she was sitting on the couch. She patted the space beside of her and when I sat down we started to talk.

She was asking me all sorts of questions like when and how did I start cross dressing, had I ever dressed for anyone else, had I ever fooled around with a guy. Again I told her no but finally admitted to her that yes I have wondered what it would be like.

I tried to answer her as honest as I could. At some point I asked her if I could get dressed, she told me she thought I was dressed the way a SISSY like me should be dressed.

After Tammy had run out of questions she took the camera and started taking more pictures. She was instructing me on what poses she wanted me to do. She finally ordered me onto all fours.

She told me to start jacking off and smile at the camera. She was walking around me snapping pictures and then she ordered me to jack my cock with my left hand and to start working a finger in and out of my ass with my right hand.

I just wanted to cum again and the fact that Tammy was still taking pictures did not bother me anymore.

I soon shot my second load onto the hardwood floor. Tammy was snapping away as I was ordered to lick my own cum from the floor. After we were done she ordered me to transfer the pictures to a CD so she could keep a copy of them.

By now it was late and Tammy said she needed to go home. I was still wearing panties and stockings. She kissed me good bye as she reached down and squeezed my cock one last time then thanked me for the CD.

"Just think about it, I got a CD from a CD." She was laughing at her own joke.

After she left I went back over the pictures that we had taken of the two of us and I came hard twice more. Little did Tammy know, but I was falling hard for her and she would not need to blackmail me to get me to do anything she wanted....

To be continued....

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