Tennis Anyone?
Keywords: Anyone?, Tennis,
1 2 3 4 5 Next
The airline check-in girl must have thought my wife Kelly was a real cloths horse. She checked the two large suitcases and I checked my one very small case. It did look like a lot of cloths for only a one-week trip to Laughlin, Nevada but the airline people didn't need to know the whole story.
For several months now, my wife Kelly and I had been having theme nights in the bedroom to spice up our marriage. We are both in our thirties and have been together for twelve years. We wanted to shake up the routine as we loved each other very much and thought it would help us stay hot for each other. On one of these occasions she got me dressed up like a woman and she got dressed up like a man and we switched roles. This included an extra attachment on her nicknamed "Mr. Big" who was 9" long and very thick. I played my role to the limit and was deflowered by my wife who was doing her best to look masculine in a grey zoot suit, fedora, penciled on moustache, and her hair up tight under the hat.
Despite her outfit, her sexy figure and feminine features were not masked well. This was fine with me; I enjoyed her effort. I on the other hand looked smoking hot as a woman. Kelly had found a pretty black wig with Darla curls that contrasted nicely with my pale skin and blue eyes. She did my makeup to the nines, which included false eyelashes, nails, eyeliner, red-hot lipstick, blush, and the works. The outfit was a slinky red dress, black stockings, garter belt, black platform shoes and a black choker. I still remember Kelly whispering in my ear, telling me how sexy I was as she fucked me from behind.
Since that night, our monthly theme night turned into dress me in drag night. Kelly loved doing me up as a girl and we started buying different outfits each month for me including a schoolgirl outfit, cheerleader outfit, several cocktail dresses, a leather outfit, and many others. She even insisted on having me shave my legs and all for each dress up night to make the effect even more realistic. We bought corsets and false boobs made of silicone to enhance my figure too. Each month I seemed to look more and more like a real woman. In the mirror, I could hardly believe it myself. Even with my sexy, hottie wife standing next to me dressed up and made up herself, I looked hot. A couple times she commented that I looked hotter than her. Sometimes Kelly would get dressed up as a man for theme nights but most of the time she liked to play 'girlfriends' and we would have a hot night of lesbian love. I loved these nights the most as we played our roles fully. We often videotaped our sessions to watch later on. Sometimes I think that Kelly would like to try a 'real' girl but was happy to use me as a substitute.
When we planned our mid winter trip, I noticed on the calendar that theme night was going to fall on our second day of the trip. I was prepared to put it off for one month, as much as it disappointed me to do so, but Kelly suggested bringing a few things and having it while away on our trip. It turned me on to think of doing it outside of our home. I let Kelly decide on what to bring for me. I know that my wife usually packs a lot of luggage but two huge suitcases full and the video camera was making my mind spin at what might be in there.
We checked into our hotel on arrival, a huge resort, with casino, pools, tennis courts, the works. Our room was huge and lavish. We had a short rest to sleep off the jet lag before waking up and christening the king size bed. It was during this, while she riding me like a cowgirl, grinding down on my cock that she came up with a plan. She suggested that we get dressed up in style and hit the lounge. It was shocking and scary to me but her pussy had such a grip on me and I was so close to coming that I was totally at her mercy. Her pussy muscles worked their magic, manipulating me to say yes to her before she continued bouncing up and down on me until I exploded inside her.
What had I gotten myself into? I was finished taking my bath, with now smooth legs, crotch, under arms, and body. Kelly applied scented oils, perfume, and baby oil to my very feminine looking body. At 5'7" and only 135 pounds, my figure was believable enough to look like a woman especially with the aid of the corset and false breasts. I ride a bike everyday and that makes my legs and bum very shapely and not too pencil like. I wrapped a towel around me as I sat in the chair for Kelly to do her magic with the makeup. She chose dark tones, as the lounge was likely to be pretty dark. The eyeliner was extra thick and she picked very long lashes. She put a crimson lipstick that was almost a blood colour on me. The ensemble that she picked out was equally as sexy. First it was the black lace push-up bra and black lace-up waist clincher, black lace boy cut panties, garter belt, and sheer black stockings with seams up the back. The top was like a suit jacket, but very form fitting and was leopard print suede material with sheer black silk sleeves and neckline. The skirt was long black linen with a button up side. Kelly insisted on leaving all but two buttons open to show off my legs right up to my garters. I put on my black curly wig and Kelly touched it up to look sexy. We added some earrings, short pearl necklace, bracelets and false fingernails. I put on my 4" black suede pumps with the ankle bracelets on them to complete the outfit. I had plenty of practice in the shoes at home but had never ventured out in them. I walked around the room for a while sipping wine, while I waited for Kelly to finish getting ready. My nerves had me quaking and I drank at least four glasses of wine to steady myself.
Kelly finally finished herself and looked ravishing. She chose a white silk blouse and form fitting black leather skirt for her outfit; She wore the same stockings as me with black 5" paten stilettos. Her long strawberry blond hair flowed across her shoulders and framed her perfect green-eyed face. We set the camera up on the nightstand and posed for a few glamour shots. I wanted to take her right there and then, but we had an agreement and she insisted we make our way to the lounge. Despite the wine, I was still nervous. I asked what to do if someone talked to us. She told me to relax, stay coy, and talk softly and lightly and say as little as possible. I had tried talking as a woman before on our nights together and had a bit of a grip on it but still figured I would let Kelly do most of the talking. My walk was good in the high heels, Kelly reassured me that I was totally passable and should stay calm and confident. We passed an older couple in the hall and they smiled and said 'Hello' but showed no signs of noticing me. We passed a few others on the way, a maid, another older couple and two teenage boys who just stared with jaws open. I overheard one say, "Holy fuck! Did you see those ladies?"
I was feeling more confident about passing as a woman and smiled at everyone I saw. In the dim light of the lounge we walked by several groups, mostly men, some couples, as we flaunted our shapely bodies and sexy outfits. We made our way to a quiet section of the bar that was dimly lit. The bartender asked, "What can I get you ladies?" which made me feel like blushing. My wife calmly asked for two Cosmopolitans. I had never drunk one, but it looked feminine enough. I reached into my clutch purse to pay for them but the bartender indicated that they were paid for already and signalled at a group of four gentlemen standing together down the bar. They were in their thirties and forties by the looks of them, all dressed in suits, probably on business, but very sharp looking non the less. I smiled and raised my glass mouthing, "thank you" to them. Kelly half giggled and waved to them to come over and join us. I poked her in the side to give her shit. Did she forget I was with her? She turned and gave me the look as to say relax.
"When guys buy you drinks in a bar, it is only polite to chat with them and flirt a little. You'll be fine honey, you're totally believable. Just follow my lead," Kelly insisted.
With baited breath, I awaited the greeting with the four men. They introduced themselves as, Richard, David, Martin and Brian. They were all handsome and well mannered as well as well groomed. They were all taller than me, Martin was 5'10" and Richard was 6'2" and the others in between. Kelly introduced herself first and then me as Mary-Ann, her pet name for me. She made up a tale of us being business partners, owners of a women's shoe store. I tried to talk as little as possible, answering questions with a short an answer as possible. I got in the habit of taking a sip of my drink every time one of them asked a question so it fell upon Kelly to answer. I got them to talk about themselves, which made it easier. Guys love talking about themselves. They tried impressing us with their prepared resume answers that included income, cars, golf handicap, and such. I faked interest as best I could, smiling and nodding. Kelly was getting a charge out of all this and allowed them to buy us a second round of drinks, the four of them fighting over who's platinum card to use. It was strange to see what a fuss guys made over women from the other side of the coin. I had to admit that I was very flattered about the attention and was enjoying the casual flirting. In my barstool, I consciously crossed my legs so that the tops of my stockings and garter straps were in full view. I made like I had no idea as they all stole looks at my sexy gams.
Brian was the first to make a move on me by leaning closely and whispering in my ear, "You're a very beautiful lady Mary-Ann, and I love your sexy outfit too." He put a hand lightly on my leg as he said this.
I wasn't sure whether I should remove his hand or not and looked to Kelly for help but she was heading to the dance floor with Richard. The music was soft jazz and made for slow dancing. I already had grabbed Brian's hand and just towed him to the dance floor with me.
1 2 3 4 5 Next
Keywords: Anyone?, Tennis,