It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement.

Ellen was very much in dressing me up from the start of our relationship. It’s something that Joan liked to do and I was all for it as the sex was HOT. Ellen somehow captured all the things that Joan and I liked to do and carried them out to our mutual enjoyment.

As the affair matured, I realized that Ellen really preferred me to wear woman’s clothing. She would open up and talk more when I was dressed. After a while I spent most of my time in the house dressed as a woman. The trade was wonderful sex.

One day, Ellen was sitting at the table and very upset. I figured she had just had another blow-out argument with her ex-boyfriend. She was nervous and fidgety, not at all like her normal self. After a few minutes Ellen said that she was going for a walk and left.

Since I was home alone, I decided to go through my stretching routine in the basement. I changed ito a leotard and tights. I pulled the hair on my wig back into a ponytail, checked my figure and headed into the basement. I popped the DVD into the DVR and began the routine.

About half way into my routine, I felt like someone was watching me. I ignored it at first and then heard a noise behind me. I realized that I had forgotten to make sure the doors were locked and was afraid that someone was breaking in.

I turned around to see a tall dark haired woman and Ellen. The woman gasped and said “he’s perfect!” Ellen was blushing and hanging back. She then stammered that the tall woman was her friend Liz.

At that point I stood up and tried to introduce myself. Needless to say, I was a stuttering blushing fool. I was also a hard-on that was painfully trapped in the leotard. I was hard to walk towards the two ladies.

Liz was a beauty. She was almost six feet tall, about Ellen’s age and had a killer body. I approached and wanted to shake hands or hug but couldn’t get myself to move forward. I could feel myself blushing as this was the first time anyone besides Joan or Ellen had seen me dressed.

Feeling the tension, Ellen quickly said that Liz and I needed to talk and that she had an errand to run. She seemed relieved as she was talking and left.

I was left there alone with Liz and knew I wanted her in the worst way. The dress she was wearing showed her figure to advantage and I needed her out of it. Liz said she had something to show me so we sat on the couch as she pulled her phone out.

Liz began by saying that she and Ellen had been friends for a long time and often shared clothing ideas but that Ellen had made a mistake and accidently sent her pictures of the wrong outfit. She then showed me pictures that Ellen had taken of me while I was dressed. In one I was posing in the door and in the second one I was tied to the bed with a dildo stuffed in my mouth. I was really blushing at this point and didn’t know what to say.

Liz continued talking and explained that she was wondering who the woman was and Ellen told her it was me.

To me, this explained why Ellen was so out of sorts lately. We continued talking and I became much more comfortable.

I then asked Liz if she wanted a coffee. Liz replied that she would and that there was a great little coffee shop down the street. I was thinking about the kitchen. Anyway this reduced me back to what could politely be called a “hot mess.”

Seeing my discomfort, Liz said that I needed to change and everything would be fine since I looked the part. She then showed me the pictures again. Feeling blackmailed, I realized that I needed to cooperate and said that I would be right back.

I headed to the bedroom and pulled my workout outfit off. My boner immediately stood at full attention, obviously happy to be free. I then heard Liz quietly say that I needed to fix that issue. She had followed me to the bedroom. I was hot, horny, bothered and any other description you could think of.

I flopped back on the bed at that point and hoped that she would join me. Instead she just stood there. I didn’t care. I began stroking myself as I needed the relief. I didn’t care a bit that she was watching. Relief came quickly as cum spurted almost to my chin.

Liz handed me a roll of toilet paper and encouraged me to get ready so we could go. I cleaned up and grabbed a fresh matching strapless bra and panty set. I slipped into a pale yellow sundress and grabbed my sandals out of the closet. I checked my hair and makeup in the mirror noting that Liz was nodding her approval.

I grabbed a small handbag with cash and a key in it, heading towards the door with Liz offering words of encouragement. I made it to the door but couldn’t bring myself to open it. I had never gone out dressed in public! Liz came up next to me and abruptly opened the door. The sun shined in and I realized that I was in public view.

Gathering my confidence, I walked down the stairs with Liz next to me. She continued to offer words of encouragement and guided me down the sidewalk towards the coffee shop. It didn’t appear to be too busy but there were people inside.

Liz sensed my nervousness and told me to go find two seats in the back. She would get two coffees and meet me there. I followed instructions grabbing two stools near the wall. Liz quickly came with the coffee.

We sat and continued to chat. I could feel eyes looking across the room at us and realized that I could find out who was looking by simply looking back across the shop. Liz also noticed and pointed out that I should get used to it. She pointed out that I had a nice looking shape and that men would look at me.

I wish I had I had Liz’s confidence! Anyway, I got used to the looks and decided that they were really looking at Liz. We eventually finished our coffees and got up to leave. Liz lead me back out to the sidewalk and I could feel the stares as we walked out. Hopefully I passed and didn’t look like a guy in a dress.

Liz walked me home. At the door she said that we should make a coffee run a habit and gave me a huge hug. I quickly agreed and asked if she wanted to come in. Liz said that she had to go to work and promised to contact me soon.

Anyway, that was my first experience out of the house and Liz did call again. Apparently I passed my test and sex with Ellen that night was hotter than ever. More to follow…..