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. He liked the idea and we held me very close as we danced. I felt a bit awkward at first but allowed Brian to take the lead and just cling to him as Kelly was doing. She gave me a knowing smile as we made eye contact and winked at me. Meanwhile Brian was snuggling himself into the nape of my neck giving it light kisses. His hand had slipped down my back and was now caressing my nice round ass. I again looked to Kelly and saw she was getting the same treatment and made no move to fight it off. So I allowed Brian his little fun and before the song ended I stared feeling something hard pressing into my hip and it took a minute to figure out that Brian had an erection.
The song ended not soon enough, as I was getting worried. Kelly and I took our partner's hands and walked them back to the bar. The other two were eagerly waiting their turns. Kelly took David and I took Martin back to the dance floor. I was more relaxed with Martin as he began making the same moves on me as Brian did. His firm hands pulled me tight to him, pressing his hard on into my hip while fondling my ass.
He whispered sweet nothings into my ear, telling me all the kinky things he wanted to do to me, including licking me all over, sucking my pretty toes, and making slow love to me. I had to admit it was beginning to thrill me. I was giving him full access to my neck to kiss and lick. With the music moving me and the buzz of the alcohol, I was forgetting my worries and my gender and when Martin moved his lips to mine I allowed him to kiss me. His firm lips pressed gently on mine and I softly yielded, feeling his tongue slip inside my mouth. The song soon ended and suddenly I felt Kelly grabbing my elbow and saying, "bathroom break".
I quickly regained my senses, realizing what I had done. I was overcome with a feeling of horror, not only at having kissed a man but of doing so right in front of my wife. Luckily for me, when we arrived at the ladies bathroom, she was in good spirits. Kelly was actually trying to hold in her laughter as apposed to being mad. I was relieved. As she pulled out her lipstick to fix herself she said, " Oh my god Mary-Ann, I had no idea you were a two drink slut!" I could only blush.
"Usually a lady doesn't make out with a guy until he's bought you dinner or at least some champaign, and not on the first dance," she continued.
I began fixing my lipstick too and had no reply to offer so I just raised my eyebrow and smiled sheepishly trying not to laugh. Kelly grinned, "Slut!" We both started laughing hysterically.
As we continued fixing our makeup Kelly inquired, "So how was it?" I looked over a bit confused. "The kiss! How was it? Did he use his tongue?" I realized that this is what girls do. They go to the washroom together and tell each other every detail of their encounters.
"It was nice, more gentle than I imagined,… and yes he slipped his tongue in," I answered. She blushed and smiled at me. I went with it, "It was long too, and he knew how to use it, bet he knows how to please a woman." We kept giggling like little schoolgirls.
"So, which one had the biggest cock?" Kelly threw out next, almost making me paint a line down my face with eyeliner. I just stared open mouth at her. "Well, try telling me that they didn't each have a hard on, and that they didn't press it into you while dancing. All guys do it, even my husband does that," she explained. The cheesy smile appeared again.
"Well, they both were big, at least seven inches long, but I think Martin's was thicker, almost like my wrist," I played along. "Yours'?"
Kelly played too, "David was big and thick but I'm sure Richard as at least ten inches. He's much bigger than my husband, that's for sure. I can imagine that big monster fucking me all night long," she added.
"Now who's the slut?" I threw back at her. We had our giggle and finished freshening up.
"Get me back in our room and I'll show you baby!" she told me obviously turned on by all this and ready for some girl on girl love.
Kelly told me that I should fake a headache so we could make our exit gracefully then stopped suddenly, "Unless of course, you would rather we went to these guy's room and let them fuck us with those big cocks?" I was starting to giggle again when I looked at her and saw that she was very serious. She was actually serious! On top of that she thought that I might want to really do that too. Of course making out with one of them would give her that impression of course. I actually hesitated for a minute and thought about it but saw all kinds of problems with that idea, like getting caught. The point was that I was actually thinking about it and the idea was turning me on. I had to shake my head and told Kelly that we should just leave and go back to our room. We had successfully impersonated me as a woman and got away with it and should quit while we were ahead.
Kelly made the appropriate excuses to the men and we thanked them for the drinks and the dances. They each gave us a hug and a kiss on the cheek. We apologized for leaving them and I somehow found myself saying, "I hope we see you here again, we'll be back another night." What was I thinking? Maybe I was a slut.
The sexual tension between Kelly and I was intense all the way back to our room. We held hands like two girlfriends and we both were licking our lips in anticipation.
We couldn't open the door fast enough. Kelly pushed me against the wall and pinned me there with her arms. She forcefully kissed me on my painted lips. She kissed me aggressively, jamming her tongue into my open mouth. She was burning up; already she had straddled my stocking covered thigh and was humping it. I could never remember being so aggressive before, I felt like she was going to rape me. Kelly was sucking my tongue almost clean out of my mouth as we kissed, our hair tangled and woven together.
After a few minutes of this heated, panting display, Kelly pulled away, breathing heavy and with a look of fire in her eyes. She deliberately hiked up her skirt and grabbed hold of her black thong panties and in one motion pushed them down to her ankles. She then stepped out with one foot and using the toe of her stiletto shoe kicked her thong at me. It landed right in my face. I took in the delicious bouquet and noticed how damp they were. I mean they were soaking wet. She must have got extremely turned on by our evening so far to get that wet. I was still enjoying the aroma when Kelly called to me, "Hurry up bitch! I'm waiting."
My love was on the bed, all her cloths still on except for her panties with her skirt hiked up to her waist and her legs lewdly spread. She was using her fingers on her shaved mound to open the soft pink folds. I strode over to the bed fully dressed still and crawled up to her spread legs. I noticed that she had turned the camera on the nightstand on. She grabbed me by the hair and pulled my face to pussy. She shoved it right in my face. I began licking her juicy box to her delighted moans. "MMmm! That's it girl! Eat my sweet pussy with your slutty little mouth," she groaned.
Her hips thrust at my face, humping my tongue. Kelly always loved how I gave her oral when I am a man, but when I am dressed as a girl and especially on this night she was over the top. I worked my tongue fast and furious on her clit as she humped my face. Kelly was on fire! She was going ballistic. "Eat me! Eat me!" she continued to cry as she began a wave of orgasms that lasted for several minutes. Her breathing was ragged as she squeezed my head with her strong thighs, cumming harder than I had ever seen. I licked and licked for all my worth all the way through.
Kelly finally released her grip on my head and caught her breath. Eventually she lifted my glazed over face up to look me closely in the eyes. "Oh, pretty girl, you did that so well," she said as she softly kissed my swollen lips. She began licking my face clean and gently kissing me. We shared a beautiful soul kiss together for a long time. She then was ready for some more. I had been ready for a long time and my panties were having a rough time trying to hold me in. She had me sit facing her and we intertwined our legs so that our crotches were pressing against each other's. I have heard it called tribbing. We ground our crotches together; hers bare and mine still in panties. Eventually she reached in and pulled out my 'clit'. She slipped it inside herself with ease. She was so wet! It felt like heaven. We slowly started grinding against each other, and I kissed and licked her ankle and foot still covered with stockings and shoes. As we slowly made love like two hot women Kelly began teasing me again.
"So, which one would you have sucked off first?" she started. I said nothing and continued kissing her ankle.
"Hmm, which one, Martin? Would you lick his cock all over first, and his balls, or would you take him deep into your throat right away?" She kept looking at me for an answer. It was kind of sexy, so I started playing too.
"Definitely Martin, and I would lick it all over first," I replied. That got a rise out of her and she grinded into me a little harder.
"Oh ya! I knew it. I know you wanted to lick his big cock all over. I bet you would suck his balls real nice too," she continued. I nodded 'yes' to her as I smiled.
"I bet you would lick his asshole too, right? I bet you would lick deep inside his butt wouldn't you?" she asked intensely, never breaking eye contact, grinding away.
"Oooo, yes, I would love to eat his asshole!" I answered licking my lips. She loved that and she grabbed my ass cheek to pull me deeper inside of her.
"Would you suck his cock real slow to enjoy it longer or would you blow him hard and fast to get him to come faster?" she went on.
"Slowly!" I answered.
"What would you do when he starts cumming?" she smiled.