okay never done this before but here goes =) So i had just broken up with a girlfriend a couple months ago, and had been feeling pretty down and unhappy. I had a friend of my f****y invite me over to hang out and play some video games and eat some dinner. When i got to their house Jan and Ted, they have been married as long as i can remember about my parents age, were glad to see me and felt some relaxing fun would take my mind off things and everyone could have a good time. So we started playing some video games and drinking some wine when ted had to get up to do a little work and left Jan and myself to play. Jan stopped the game shortly after he left and came over and sat next to me, which wasnt out of the ordinary. She leaned in close and asked me if id like to be her cute play thing for a little bit. I was totally off guard to that and never expected Jan to ever ask me something like that, and asked her if Ted knew. Jan put her hand on my thigh and said, "its ok, he knows and would like to see. I instantly turned red but was really interested, Jan is a gorgeous fit, toned, and tan mid 40's housewife, and I wanted to play along and have fun. When i said okay Jan smiled at me very sweetly and got up and said "ill be right back, don't get cold feet" and walked out of the room. When Jan came back she had a handful of things and camera. I was a little nervous when i saw the camera, and what she had in her hands. Jan walked over to me after she had changed into something ridiculously sexy and hand took what she had in her hands and gave it to me and said, "now go put that on for me and call me when your dressed." I took what she had and went to the bathroom, and after tossing things onto the sink i realized what clothes she gave me. Jan had given me a pair of sexy stockings, a thong, a sexy black dress, bra, wig, and stuffing for the bra. I sat there a second looking at everything thinking... "she wants me to crossdress for her?" I had never worn or thought of wearing women's clothes before but i thought this might be a once in a lifetime chance so i decided, why not try it out you never know i could like it.. After putting on all the clothes i called Jan and she came in telling me how good i looked and that i should think about putting on sexy clothes more often. I was a lil on edge feeling not so comfortable in girls clothes around really good friends of my f****y... but decided to go with the flow. Jan open a drawer and pulled out some makeup and said, "now im gonna get your finer girly details" and she painted me up in makeup. I was amazed how good i looked afterwards. i couldn't even believe it was me, id fuck me if i didnt know i was a guy haha. So now that i was all dressed up like a cute girl for her, Ted came back in the living room to take a seat on the couch and loved how i looked! I had never had another guy look at me sexually let alone tell me ow good i looked or want to touch me. Normally i wouldn't care at all, but for some reason being all dressed up and feminine looking, it turned me on. Ted sat and watched Jan and i together, encouraging us the whole time. After some wonderful foreplay Jan told me its time to fuck and, she looked at me and grinned and said "im gonna go get my strap-on and fuck you, how do you feel about that" I probably turned white but since things had been going so well and i was super turned on, i wanted to at least try it. So Jan went and got it and walked back in with what in my eyes was a monster cock. I had never been so nervous yet turned on at the same time.. Ted watched as Jan slowly dominated me, having me please her, suck her cock, and then the moment i was so nervous about happened. She had me get on all fours and slowly slid her dick inside me. i couldn't help but let out a little yelp of shock but bliss. Jan slowly pumped me and told me how good of a girl i was, while Ted encouraged her and me. I couldn't keep quiet not even if i tried... And had the best most amazing full body orgasm of my life. After we finished Jan gave me huge hug kiss and ass grab and told me if i ever need to be treated this way again im more than welcome to cum back again and we could keep everything secret and nobody would ever know. After that day i started regularly going over there like twice a month to be Jan and Teds special girl. I never thought id ever get into kinky play like that but it was one of the best times of my life. and even though im a straight masc athletic guy, i miss being Jan and Teds submissive sexy gurl...