I'd been slowly easing my wife Lisa into my fantasies for awhile now. We're in our early 40's and have been married almost 20 years, so we had to find ways to mix things up a bit. It started with her wearing leather and pvc clothing for me, allowing me to shoot photos of her and fucking. She's so fucking hot, even though she's in her 40's, she has the body of a 21 year old, 5' 7", 145 lbs, great legs, great ass (she works hard on them at the gym) and nice tits and a pretty face. Then I started dressing up as well, still as a man, but wearing pvc or leather pants a shirt, jacket and tie, then it was chaps, bondage and domination really fast.
Well, when my wife leaves town I was crossdressing, dressing up in all the different outfits I could put together — mostly the stuff I bought for her that was big on her. I love how my legs look in heels and seeing myself in bright red lipstick. Eventually my fantasies evolved into wanting to dress up like a slut and having my wife fuck my ass with a strap-on. Then later, although I never thought I'd do it, I fantasized about sucking and fucking a real cock.
Finally I slipped up, left some make-up out and my wife asked me about it. I came clean. She was initially a little apprehensive, but eventually a smile crossed her face. I then added that I'd like her to take a masculine stance and fuck me with a strap-on every once in awhile and she just widened her smile and nodded and walked out.
Several months later I was walking in the door from work and Lisa was sitting on the couch in her typical domme garb: black leather blazer, white satin blouse with pearls, tight black leather skirt that came to her knees, stockings and black patent 5" heels. She had her hair back in a ponytail and all she said to me was, "John, we're going shopping. But first, if you haven't shit today, go do it." I immediately went to the bathroom.
She took me to the leather store first. As we were driving I just kept my eyes on her legs and her leather covered body. When we got to the store she headed directly for the women's leather pants and she quickly picked out a pair of tight, but masculine looking ones for her (she had several ladies pairs already) and a pair of tight feminine ones for me. She then walked over to the skirts and picked out three for me, a very short one, a knee length one and an ankle length one, all tight. I was marveling at her efficiency as she barely spoke and moved with a sense of purpose. She grabbed two leather dressed, both short and two leather vests, a ladies' and a men's. She grabbed a couple hats, collars and a few other miscellaneous items and then announced we were done. She ordered me to the car and I went.
Next stop was the women's shoe store. She picked me up a pair of black patent knee high boots, black patent pumps, black patent strappy heels and a pair of brown leather boots — all 5" heels. From there we went next door to Target and she got a cart. She filled that cart with all kinds of goodies: eye shadow, mascara, lip stick, lip gloss, foundation, pantyhose (the sexy kind with the seam up the back), nail polish, thongs, granny panties, tampons, KY Jelly, razors, women's deodorant, perfume, a few cute tops and dresses, a pair of dark skinny jeans, another pair of tight jeans she told me she planned to make cut-offs to go with my heels, a couple satin bras (white and black), a couple nice business looking outfits including my very own satin blouse and jewelry (just clip on ear-rings, necklaces, bracelets and rings).
When we got home Lisa demanded a fashion show. She took me into the shower, watched me shave my face, legs, armpits and chest and trim my pubic hair. She trimmed my eye brows and dried me off. She applied the bright red nail polish to my fingers and toes and sat there as it dried. She got up and found me a nice wig from her collection: black, short bangs and shoulder length. Then the fun part began. She had me put on the skinny jeans, the brown boots and a nice blouse. She then helped me with my make-up, making me look really slutty, with a lot of eye shadow, deep red but bright lips and put the wig on and allowed me to admire myself in the mirror. As I saw myself I felt my cock push on my thong and drive it up my ass, this only turned me on more.
After trying on several more outfits, we got down to business. She allowed me to admire myself while she left the room. When she returned her hair was up under one of the leather hats she bought, her make-up was off and she was wearing a leather vest under her blazer, her tight black leather pants she just bought and manly looking leather boots. On top of all of this was her strap-on, the cock was about 5", not too big, but I'm a beginner, so big enough to be enticing.
"Okay take off the pretty clothes, and put on the slutty clothes I bought for you." She then went to the bag and got out the black pumps, black seamed pantyhose, garter, short black leather skirt, a wide belt, the satin blouse, some fake pearl necklace and bracelets. I got dressed and she allowed me to admire myself in the mirror for a few moments.
Once she thought I had looked at myself long enough she pointed at the desk. "Go sit down. You are going to be my secretary, Jennifer. I am your boss and you will do as I say, understand?"
With that she came over, lifted me out of the chair and began kissing me forcefully. After a moment, she simply grabbed my head and forced me down to her cock and I wrapped my bright red lips around that rubber cock and I sucked it hard. I had been dreaming of this for a long time so I was afraid I'd cum too soon, so I sucked her like she had sucked me all those years. Soon she was fucking my mouth and I was gagging, she seemed to enjoy this.
"Get up and go over to the bed Jennifer."
I did as I was told and she then surprised me, she grabbed some handcuffs and cuffed my hands to the bed posts. Then she tied my legs with rope to the bed post. She then walked to a table and picked up a cell phone and dialed a number. "Come on up, he's all tied down."
I had no idea what was going on. Soon a buff young stud, no more than 21 comes into the room. He's carrying three wine glasses, two bottles of red and his wearing a leather harness, tight leather pants with an opening for his cock and black boots. I look at Lisa with a surprised looks and she just turns to him and says, "You get to live out your fantasies, then so do I and then some." He pours two glasses and they take a couple drinks and then start to kiss, her one hand on the wine and the other stroking his noticeably large hard-on. They both step away from one another and take a couple drinks of wine and she says to him, "You ready?" and he nods.
.... There is more of this story ...