This story contains TG themes and depicts acts of sex and is not intended to be viewed by minors.
Marty S
TENNIS ANYONE
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.
"I would take him deep and swallow it all," I said boldly.
"Oh god! I knew it!" she panted as she threw her head back in passion on the verge of her next orgasm. She regained her composure and fixed her eyes on mine again.
"What if he wanted to fuck you? What if he wanted your sweet little girl ass?" Kelly asked.
"MMmmm, I hope so, I want him to fuck me, I want him inside me," I told her making her bite her lip. She smacked my ass real hard, making it sting. I went on, " but he would have to wait his turn because while I have been sucking his cock, Brian has been pounding my little bottom with his big cock." That did it. Kelly went over the top again, franticly fucking, screaming in orgasm, all the while slapping me hard on the ass.
She rode me fast and hard screaming, "You dirty slut Mary-Ann, you sucked all their cocks and let them all fuck you, and you loved it you dirty little tramp! Ahhhhhhh!"
That put me over too and I could not hold back, blasting my orgasm deep inside Kelly's blistering honey-pot. We both crashed.
The next day things started out fairly normal for us. We were still reeling with euphoria from the night before but we had breakfast and went to the spa together. We had a light workout, a swim and a relaxing massage. I remember wishing I could be a woman with Kelly and have our massages together, but I had mine separate. The massage was soothing even though I had it from a big blond muscular kid named Harold. As he worked my back and shoulders I began drifting off and reminiscing about the night before, flirting with the men and talking dirty about it with my 'girlfriend'. The thoughts were exciting and the stimulation of the massage was all beginning to get me aroused. My dick pressed freely on the terrycloth towel helped too. Soon I had a full erection under my towel as Harold started working my shaved legs. I wondered how many smooth shaved men got massaged like that. Suddenly Harold raised my towel a bit to work my upper thighs and I realized my hard cock was exposed to his view. In a brief panic I pulled the towel down and suggested stopping the massage. I was embarrassed and was turning red. Harold asked if anything was wrong and said it was fine with him to continue. I looked at his face. His blue eyes showed sincerity, which made me feel better but I opted to call it off anyway. I gave Harold a generous tip and told him I was late for meeting my wife.
Kelly and I had a light lunch and returned to our room for a shower. We jumped in together and I still had a semi boner from earlier that sprang back to life at the sight of Kelly's toned body getting soapy and wet. She asked me about my massage and I went ahead and told her the details. Kelly got very turned on hearing the details and she began stroking my hard on and rubbing my smooth ass. She began teasing me again, "I bet Harold was totally ready to fuck you."
Kelly's fingers were circling my tight little hole. "You wanted his cock in here so bad!" she taunted as she pressed a finger inside me. My cock was straining at full length. She had no trouble working her soapy digits into my back door. Soon she had three in me.
"Harold's little whore wants to be fucked real hard and fast, doesn't she?" Kelly teased as she probed me and had a lick up my cock with her tongue.
I was so weak with lust at that point, I replied in my best girly voice, "Oh yes Harold! Fuck your sweet little baby nice and hard."
Kelly liked that and she wrapped her mouth around my cock and sucked it deep right away. At the same time she fucked my ass with her fingers like a pneumatic jackhammer. She pumped the head with her warm, wet mouth and I simply could not take any more. I started cumming like a geyser, filling her mouth with my salty sperm. When my orgasm subsided, Kelly released her lip lock from my cock and stood up to kiss me full on the lips. My open mouth was soon being filled the warm sticky goo from my wife's mouth. She kissed me so hard I no choice but to swallow my cum. She seemed very pleased with that and had a smile like a Cheshire cat. Her fingers eventually exited my bum and she stepped out of the shower. Before I could get out, Kelly reminded me to shave again, extra close, all over.
I did as directed figuring Kelly was planning another dress up event. I was eager as well as a bit frightened at the prospect. Kelly helped me after the shower to get beautiful again, but it was still mid afternoon. It seemed too early to start getting ready. Kelly then informed me as she applied baby oil to my smooth legs, "I booked a tennis lesson for 3:30 for me and Mary-Ann"
This would be very different than before, not only would this be public again but in broad daylight, in front of sober people. I was getting worried. Kelly helped make my make-up look appropriate for the daytime. "What about sweat?" I asked.
"This is the most run proof, top of the line, athletic approved stuff on the market," she tried to reassure me. She also thought it was a good idea for her not to wear any make-up at all so that the contrast made me appear more feminine. She simply pulled her hair back into a ponytail and put on a light coat of lip-gloss. She made sure my wig was pinned in good and put a bandana on my forehead to keep the hair out of my eyes and to absorb sweat. She pulled out a tennis outfit for me that included a white women's sports bra, a pair of white panties, a white tee shirt with pink stripes that had a scoop neck and frilly pink lace around the sleeves and pink trim around the neckline. The skirt was a pink pleated tennis skirt barely long enough to cover my bottom. I had little white ankle socks with lace trim to wear with my tennis shoes. With the outfit on, I felt more like a princess than an athlete. Kelly actually looked a bit butch standing next to me in her all white tennis outfit with no make-up. I asked if lessons were really necessary since I was already very good and often beat Kelly on a regular basis at our club back home. She smiled and said it would be different this time and reminded me that I had to stay lady like, even on the court.
We arrived at the tennis courts on time and met our instructor, Andy, a six-foot tall, African-American hunk. I recalled seeing him earlier in the health spa. He was a very attractive man, as men go I guess. He was very polite greeting us, "Afternoon ladies, looks like my last lesson today will be my best one." What a flirt! "Both you ladies look like your in great shape, I bet you could even teach me a thing or two," he smiled and winked at us. I bet he got more pussy than he could ever handle.
The lesson went well. I had a much more difficult time than I imagined trying to play tennis as a woman. First, my balance was shot to pieces because of the breasts. Second, I had to always be cautious of my skirt riding up, so I found myself moving a lot less. Third, trying to keep looking pretty and not sweating like a man meant restricting my level of intensity. I was thinking more about loosing a fingernail or if my hair was still straight as opposed to paying attention to my game. It made a huge difference. In the practice set, Kelly was kicking my ass. She relished the situation, trying best not to openly laugh at me.
Andy was very flirtatious with both of us. He would often help us with our posture and stance by standing directly behind me and holding my wrists while his face was next to mine, whispering instructions in my ear. His manhood could easily be felt pressing up against my behind when he did this. He was full of compliments the whole time. He whispered to me, "Your much sexier than that Anna Kournikova," as he patted me softly on the ass. Kelly was looking over at me with a smirk on her face, biting her tongue, knowing full well what he was doing. He was doing the same thing with her as well. This went on for the full hour. I couldn't believe the moves this guy had.
When we were done, we thanked Andy for the lesson with a kiss on the cheek, Kelly on one side, me on the other. He blushed and then made a slight painful wincing. Kelly asked if he was all right. He grimaced and claimed that he had an old injury in his shoulder and it was sore from a full day of lessons. "Good thing they have so many good masseuses here," I said coyly.
Andy made another painful face and said, "Shame us employees are not permitted to use any of clubs facilities for our private use," he replied in a seemingly rehearsed tone. It was obvious where he was going with this. Kelly fell right into it. She snuggled up close to me, grabbing hold of my hand and doing a nervous little dance with her feet. "Well, we are by no means professionals but we have been known to give a pretty good massage before," Kelly implied.
Andy raised an eyebrow. "The two of you? Both together?" he grinned. "Oh, I wouldn't want to bother you with my problem. I am sure it will be okay in a couple days," he added. He continued to roll his arm in pain. "Really, thank you for offering but.."
"Oh, no really, we insist!" Kelly began. "Right Mary-Ann?" she questioned, looking at me for support while squeezing my hand and rubbing up against me in anticipation. Her eyes were agape with excitement. She had that look that I could not say no to.
"Of course! Really, we are very good," was all I could muster.
"After all, it's our fault that you got like this. We were working you too hard," Kelly flirted. I noticed she put extra emphasis on the word 'hard'. She started twirling my hair and grinning at him, playing up the bisexual hotties role. I playfully ran a finger down Kelly's neck and smiled at Andy too. We both kept our arms back and our chests thrust out, hips cocked to one side, a very alluring posture.
Andy let out a big practiced smile, "Well, okay, you forced me into it. Just give your room number and I'll be right over after a quick shower." I wondered how many times he worked that scam.
Kelly and I quickly made our way back to our room kicking off our shoes and socks. We fixed me up as fast as possible, removed my bandana, and fluffed up my hair. We sprayed some perfume on each other and Kelly let her hair free and added a little make-up. We ran around hiding all my male cloths and any other clues we could find. Kelly set up the video camera pointed at the bed and hid it with a hat.
Only a few minutes later there came a knock at our door. He didn't waste much time. Kelly let Andy in and she stood on tiptoe to kiss him on the cheek. He gave her a polite peck back. I was getting him a cold beer from the mini fridge and he gave me a similar kiss when I offered him the drink. I blushed. Kelly laid a large towel on the King size bed and handed a very small towel to Andy to change into. She also had retrieved the bottle of baby lotion from the bathroom and brought it to the bed.
Andy changed in the bathroom and held the tiny towel loosely around his hips. His body was chiselled ebony. He had six-pack abs and a body builders arms. He was grinning from ear to ear. We ushered him over to the bed and he lay down on his stomach on the towel. Kelly and I both worked some oil on our hands and proceeded to rub the suspected sore shoulders of Andy. Andy began giving us some appreciative moans and groans as we kneaded his dark flesh. Soon he began getting playful and I could feel one of his hands on my leg. I looked over at Kelly and noticed he was doing the same to her. I spotted his hand sliding up her leg and under her tennis skirt. Kelly didn't flinch to my amazement but I then began feeling his other hand slowly moving up my leg too. I had to move before he touched my panties and discovered my secret.
Moving down his body, I started massaging Andy's legs. In my haste to get away from his hand I accidentally knocked the skimpy towel off of Andy's muscular ass. I gasped and bent down to pick it up but Andy gave me a, "It's cool baby, just leave it on the floor. Feels better this way."
From my low vantage point I could also see up my wife's skirt and noticed that Andy was rubbing her wet panties with his fingers. Shocked, I looked up at Kelly only to see that devilish smile on her face and pure lust in her eyes. I didn't know if I should feel jealous or excited. Excitement was beginning to win over. She adjusted herself to be directly in front of Andy with her cleavage staring him in the face. He continued to feel her up under her skirt and I just worked away on his lower body. As I massaged his thighs, I could see Andy's cock growing between his legs. It moved snakelike down his leg getting fatter as it did. I had never seen one that big before. I guess there could be some truth to that old cliché.
I was mesmerized by Andy's large tool and failed to notice Kelly just inches from my face. She could see it too and I was busted for staring at it. This was working to her pleasure as much as the hand moving more rapidly under her skirt. Kelly grinned ear to ear. I asked her very softly if his finger was inside her. She nodded 'yes' to me. She paused for second while her eyes were glued to mine then whispered, "Are you okay?" to me. She was obviously worried that I might be getting jealous. I was a bit but part of me wanted to see this all out and I found myself nodding back to her. Kelly smiled and pulled me closer to her and we shared a loving soul kiss. In our passionate embrace I failed to notice that my hands were now firmly on Andy's butt and I was giving his cheeks the full massage.
Andy soon became aware of the girls kissing behind his back. He tried to turn himself over to get a better look. Kelly kindly moved herself so that Andy could get a better view. "Oh yah! That's what I'm talking about!" came his approval.
"I love that! Do you ladies know how hot that looks?" Andy interjected but Kelly and I just kept making out. Her kiss was intense and I responded in kind. My feelings on everything up to that point were that it felt on the verge of getting way out of hand but Kelly seemed to know exactly what she was doing and everything was under control.
Andy sat up and moved inches from our faces. "Mind if I join in?" he asked coyly. Kelly reacted by turning to him and planting her mouth on his. I had never seen my wife kiss another man before but it was very erotic. She had left her hand around my head and was stroking my hair for reassurance. It was an amazing site. Their skin contrast added to the visual stimulation as well. Their kiss was hot and heavy, with tongues rolling in and out of each other's mouth. I was drawn to it. Before I knew what was happening, Kelly broke her kiss with Andy and pushed my head towards his face. Suddenly I was lip to lip with my black, hunky tennis instructor. His tongue had soon entered my mouth and I almost instinctively started sucking on it. His kiss felt as good as it looked. Kelly didn't need to hold my head in place as I was soon giving as good as I was getting. It was only my second kiss with a man but already my instincts were feminine, responding softly and yielding my mouth.
I was enjoying the kiss when I felt Andy's hand sliding down my back and grabbing a handful of my ass on the outside of my tennis skirt. As much as I hated to break the kiss, I jolted again to break his hold. I panicked and didn't know what to say. Andy had a disappointed look on his face. Kelly quickly interjected, "Oh, don't worry, Mary-Ann is not a prude, it's just her time of the month and she doesn't want anyone swimming in the red sea, if you get my drift."
It was a good catch. Andy smiled and looked relieved at me. "That's cool baby, can I just touch your butt instead? I have dreaming about those sweet buns since I first saw you on the court today," Andy pleaded. I winked and took his hand and placed it back where it was on my ass and helped him give it a squeeze. It felt good. His hand was massive. I quickly looked down and noticed two other things; Andy's other hand was on Kelly's bare ass. Her white panties were now down around her ankles. The other was Andy's big cock was free and at full mast, standing ten inches from his lap. It was dark and meaty with a big angry head on it. It looked so powerful. Kelly ran a finger down its length and gently took hold of Andy's big bouncy balls.
"You alright baby?" Andy asked. I raised an eyebrow and nodded. He pulled me to him again and I eagerly kissed his mouth. We frantically made out again, returning to the level of passion from only a few moments earlier. Andy continued to fondle my sweet ass. My eyes were closed as we kissed but I became aware of soft hair gliding across my arm that was resting on Andy's thigh. I looked down to see Kelly's head in Andy's lap. She was licking up and down his giant cock with her wet tongue making it glisten with her saliva. Andy moaned deeply. He was still sucking my lower lip while I watched my wife lick him like a lollipop. Kelly noticed me staring at her. Her green eyes were wide open with excitement. She smiled and opened her mouth wide devouring the head of Andy's cock. Andy reeled in ecstasy as he lay down on his back to enjoy this blowjob. Kelly choked half of Andy's rod into her throat. Her cheeks hollowed as she slowly sucked her way back up to the bulbous tip. Very slowly her mouth disengaged the wet shaft leaving a tiny trail of precum from the head to Kelly's lower lip. She again made intense eye contact with me. She crooked her finger to signal me to come closer. I moved closer so that my face was inches from hers with Andy's cock between us. Devilishly she whispered to me, "You want some of this?" while holding the massive prink an inch from my face. I was speechless and didn't know how to react. Part of me wanted to join in but was afraid to. I just stared with my jaw hanging open. Kelly could see I was mentally debating the issue and decided to help me choose by rubbing the gooey cock on my face. She glided it across my cheeks and my wet lips. As it passed I let my tongue have a lick.
I closed my eyes slightly and gave Andy's prick a nice long tongue bath, licking from top to bottom and back up again. My tongue circled the dark coloured head lapping up the precum and Kelly's saliva. I was committed now and Kelly pulled the back of my head so that Andy's cock slid right into my mouth. My lips slid down around his delicious tool until the head lodged in my throat. I slowly sucked my way back up and off the cock. Kelly planted an open mouth kiss on me, licking the inside of my mouth. She was burning up. I could tell she was horny as hell. Andy was helping her along by finger fucking her with two fingers in her pussy and two in her asshole. She loved it. I was too and had to fight to keep my own erection from climbing out of my panties. I squeezed it between my thighs where it was kept still.
Kelly and I kissed passionately sharing the flavours in our mouths until she broke it to return to sucking Andy's cock. She took up sucking the top part of his cock while I started licking the lower part of his shaft and sucking his big balls. His balls were neatly shaved and smooth. They were so big; I could barely fit one in my mouth. I back and forth tasted each one and licked that sweet spot at the base of cock that I loved having licked myself. Kelly then relinquished her monopoly on the head and I took over sucking it while she did some licking on the lower shaft. We continued to swap duties sharing equal time with the cock in our respective mouths. Sometimes between turns Kelly and I would share a little kiss and lick the precum from the other's tongue. Andy was in blowjob heaven, having his big black monster cock sucked by two hot babes. It was on one of Kelly's turns with Andy's dick in her mouth that it started to erupt. She was caught a bit off guard and her eyes opened wide. I could tell what was happening. She must have taken a healthy blast down her throat. Kelly pulled her lips off of the tip and a white salvo splashed across her lips and face. She aimed the cock at my waiting mouth and a blast hit my face before I could wrap my lips around it. Soon I felt shot after shot filling my mouth that I tried desperately to swallow. His sperm was hot and creamy. It tasted different than my own which had previously been my only sample. I must have looked like a real slut as I gulped down Andy's load. Kelly seemed to enjoy it and started cleaning my face with her tongue. When the flow of cum stopped I let the sticky cock fall from my lips and I started licking Kelly's face clean as she had done for me. We then shared a hot cummy kiss with a snowball of Andy's cream on our tongues.
I was so turned on by all this it was getting tougher to hide my excited member. Andy's hand was still squeezing my bum. I had to squirm to keep his fingers from locating it. Suddenly Kelly leaned closely to my ear and whispered urgently, " You have to fix your makeup!"
I got up and sprinted to the bathroom, excusing myself as I ran, "Gotta pee!"
Once inside the locked bathroom, I saw that my makeup was almost completely gone. It may have been sweat proof but it wasn't sperm proof. I got to work fixing it as best that I could. The eyes didn't need muck work, mostly the cheeks and the lips. I tried to do what Kelly had taught me and was soon looking like the very feminine Mary-Ann again. I was still hard as a rock and thought it might be a good opportunity to unload the burden. I dropped my panties and my painfully hard prick sprang up. In only a few short strokes my aching member was unleashing its pent up frustration. I felt a lot better after that and straightened my cloths out. Once I was convinced of my feminine allure once again, I sprayed a little more perfume on and returned to the room.
What I saw as I walked back into the room almost made me blow my cover. Kelly was on her back, her feet high in the air over Andy's shoulders. Her top and bra were gone and her skirt was hiked up over her hips. Andy was on top ploughing into her moist pussy. Kelly's eyes were half closed as if in a trance. Her tits flopped up and down in rhythm with the thrusts of Andy's pelvis. I thought I had seen serious fucking before in porn movies but what I was watching put all that to shame. Andy drew his cock all the way out to the tip, then slammed all ten inches back in hard at a steady fast pace. His athletic prowess really showed as he gave Kelly the fuck of her life. The flexing of his well-developed ass cheeks and his long, thick shaft plunging in and out off of Kelly's helpless pussy mesmerized me. The sounds were very stimulating too with the slurping sound from Andy's cock pulling out, the slapping sound as his balls smacked her ass on the way back in, Andy's grunts and Kelly's panting and moaning. They were oblivious to my presence and it made me feel jealous that I wasn't involved. It was half, my wife being fucked by another man and half; I wish it were me getting fucked like that.
Kelly looked as if she was very close to another orgasm from the drilling she was receiving and I got a little closer. She sensed my presence and suddenly pulled me closer and locked her lips on my mouth. Her kiss was hard and forceful as I felt her entire body tense in orgasmic bliss. Andy's cock continued to slam into her for a few minutes while she came and came again. Finally, Kelly broke for some air, her chest heaving and panting. She squirmed up the bed, to slip out from under Andy. Her body glistened with sweat and her hair was drenched as well. Andy had not come yet and he knelt on the bed with his massive boner standing in front of him all shiny with Kelly's love juices. He was slowly stroking it with his hand. I salivated looking at it and instinctively lowered my face until my ruby lips had wrapped around his cock. I loved the mixed flavour of man and woman. I gave it a fastidious tongue bath. Andy wanted something more however; he pulled my face from his prick and up to his mouth. He kissed me passionately, which surprised me judging from where my mouth just was. The kiss was hot but gentle and loving.
"You want some of that too? Just like your girlfriend," Andy inquired softly. Had he forgot?
I hesitated but softly replied, "I can't do that right now, remember?"
He answered back as he fondled my bum, "How about back here? You like back door lovin' girl?" I was silent for a moment as I prospected the image in my head. He kept prying, "I've been dreaming of this sweet bottom all day since I first saw you on the court."
I was melting at his sexy words and soft but firm touch. I had to reluctantly stop him before it got out of hand. "I don't think it's a good idea, sorry baby," I finally answered.
Andy whispered into my ear, "I have to let you in on a secret of mine." I curiously leaned back to hear him out. He started, "I remember seeing this good looking couple this morning in the spa, husband and wife, the guy was thin and had a clean shaven body, kind of feminine I thought." "The pretty wife was this hot little woman right here," he added pointing to Kelly. "So, when I saw the same woman on the tennis court this afternoon with a hottie girlfriend instead of her husband I got thinking about it. Could it be possible that the girlfriend is actually the husband with women's cloths, a wig and some makeup?" he asked with a sly, devilish grin. It appeared that he knew it all along and before I could say anything, Andy had slipped his hand inside my panties and was touching my cock.
I was frightened and in a panic. I wanted to run away and cry. Andy held on to me and calmly got me to settle down by holding me close and reassuring me. I really felt more like a girl at that moment than any other. As he brushed his hand along my hair he looked me in the eyes again asking, "So now that the cat is out of the bag, what do you say? Ready for some of that back door lovin'?"
I was still hesitant and started shaking my head "no" but Kelly had just clued in and propped herself up to answer for me, "Don't lie you fucking slut, you love getting fucked in the ass!" She was referring to our private sessions with Mr. Big of course. Soon she helping me out of my panties and I let her take them off. It felt very weird to have my erect dick dangling free under my pink tennis skirt. I was being positioned by both of them so that I was on my elbows and knees and my butt pointed lewdly up in the air. Andy moved in behind me between my legs. His fat cock felt like a lead pipe as it rested between my smooth ass cheeks. His fingers found there way to my mouth. I knew what to do and made sure to get them soaking wet with saliva. Andy withdrew them and soon I felt his digits playing with my tiny ass hole. He worked the saliva in slowly and I began feeling ready for something bigger. Kelly was back there, using her mouth to lubricate Andy's cock even more.
I had begun breathing deeply, knowing how it helped ease the pain of insertion. I found myself grinding my butt back against Andy's knuckles. Andy knew I was ready and he placed the head of his fat cock against my slightly dilated sphincter. There is no lying about it; it hurt even though he was pushing very slowly. He had obviously busted a few asses in his day. Slowly I was impaled onto his cock. It took several minutes of sharp pain before my rectum was full of meat. I continued to breath long and deep to ease the pain and tried to distract my mind from it by imagining how hot I looked getting fucked by this ebony god. Suddenly, I was treated to a new feeling I was not expecting. Kelly's hot, wet tongue was licking my dangling 'clit'. She had crawled under me and placed her face right where the action was. The pleasure I was feeling distracted me enough until I felt Andy's balls touching mine indicating that his ten inch cock was fully home.
The pain was subsiding and Kelly's cock sucking was making me forget any of the pain at all. Andy drew back all the way to the head, then eased back inside my bum all the way again. I let out a moan of approval. It felt great. Andy nuzzled my neck moaned too as he started a slow rhythmic pumping in and out of my ass. Kelly was enjoying the close up show and showed her appreciation with a stellar blowjob. Andy picked up the pace a bit. I found myself grunting, "Yes, fuck me harder, fuck me faster, I love it!"
Andy obliged me and began giving it to me hammer and tongs. He held tightly onto my hips and really worked my tight little hole. I was soon getting fucked with the same fury that he gave Kelly. I was in so much pleasure I couldn't hold back my orgasm for very long and I unleashed a torrent into Kelly's waiting mouth. She quickly pulled off and brought her mouth up to mine so that we could again share a nice hot and sticky snowball kiss. We swapped my cum back and forth which provided enough amusement to Andy that he slammed his cock into my ass balls deep and let go another gusher of his own. My rectum filled with his salty fluid. We all were breathing heavy and took a few minutes to come down. Andy then knelt in front of me so that I could lick his cock clean. While I performed that duty, Kelly got behind me and licked my ass inside and out.
Everyone was pretty spent and Andy eventually excused himself, leaving the room after giving both Kelly and I a kiss. After a quick post-coital nap, I jumped in the shower with Kelly. I asked her what she felt like doing for an encore. She told me that she had already made plans. I was anxious to hear them but I was surprised to hear that I would not be involved in them. Apparently, while in the spa earlier, she had made a new friend. The masseuse she had, Amy, a late thirties blond woman, made a move on her with hands, venturing into private territory. Kelly had told her that she would meet her here in our room later. The problem was that Amy was only interested in Kelly one on one. Kelly had wanted to try sex with a woman for a while but never had the opportunity. Dressing me up had been a substitute for the real thing. I was feeling disappointed about being left out and replaced but Kelly assured me that I wasn't being replaced. This was a one in lifetime chance for her and I wouldn't stand in her way. She also told me that she would tape the tryst for me so I could watch it after. I hoped that I had brought enough blank tapes.
Now I had to figure out what to do myself. I was feeling very confident about my ability to pass as a woman and was confidant enough to try something more. I told Kelly that while she was entertaining her masseuse Amy, Mary-Ann would make a solo trip to the cocktail lounge. I rummaged through the items of clothing in the second suitcase and selected some choice items. I started with a black garter belt and black fishnet stockings. Next were black thong panties and a black corset. I selected a silk red Chinese jacket that had dragons embroidered on it. It matched the cocksucker red lipstick, and nail polish I was wearing. The collar was high, the sleeves short and the fit was very snug but it looked fantastic with my black hair. I selected a way too short black leather mini skirt that had a little slit over one thigh and a pair of paten red platform stripper shoes. I added the appropriate gold accessories and black choker to complete the look. After I had finished dressing and finishing my makeup and hair, I modelled for Kelly.
"So, how do I look?" I asked.
"Like a hooker!" Kelly replied with an expression of disbelief on her face.
I smiled proudly, "Good! That's the look I'm going for."
Kelly and I wished each other luck and I ventured off on my own as Mary-Ann to the hotel lounge. Not surprising, I was greeted with many glances and shocked expressions as I entered. After getting myself a Cosmo, I was again told that it was taken care of. The bartender pointed out the same group of gentlemen from the previous night. I smiled and seductively sauntered over to their booth to join them. They were all in agreement that I looked fantastic. I always knew women dressed too conservatively. One of them asked where my friend was in reference to Kelly.
"Back in the room with a migraine I'm afraid," I said. "Looks like you will have to settle for just little ol' me tonight." They didn't seem too put out by that and Brian was first to drag me to the dance floor. As I danced with Brian he aggressively fondled my very popular ass. He pressed his body close and I could feel his bulge rubbing against me. After that dance, Richard took his place. The story was the same as it was with Martin and David who fallowed, each feeling up my ass and rubbing themselves against me. At the end of each song they would give me a little kiss. After they had all had one dance, they rotated through again. The story was the same with the addition of some kisses on the neck and cheek. It was definitely getting steamier. All four of the men seems very interested in me and my early departure from the night before appeared to be forgiven.
The dancing was tiring so I took a break for a drink. Soon Brian was bugging me to go back to the dance floor with him. My feet were really killing me in those shoes. I didn't want to be a party pooper again so I jokingly asked, "How about a nice lap dance instead?"
Brian's eyes lit up. "Sure, great idea!" he spouted. What had I got myself into? Brian pats his lap indicating for me to sit down. I carefully sat on his lap keeping my knees together so that my male parts were safely between my thighs out of any possible contact. Right away, I could feel Brian's erection through his wool pants and my leather skirt. The other four gentlemen watched intently as I began moving my hips in time to the music, grinding on Brian's lap. The tablecloth hid everything happening below the waistline from view of other patrons and the staff. Brian began feeling me up all over my legs. I had to divert his hands from my inner thighs a couple times. I took hold of them and moved them to my boobs. He enjoyed the feel of my fake tits. The silicone gel made them very realistic to the touch. My silk top provided a good shield from his curious hands. It began to get very erotic and my bum was feeling hungry again. I then did something that still amazes me. Right there, at the table, surrounded by people, I reached back and unzipped Andy's fly. I reached inside and pulled out his stiff member. I pulled out a small bottle of hand cream from my purse and put some in my palm. I rubbed it up and down the shaft of Brian's cock. My skirt was so short that I only needed to slide my panties an inch to the side to expose my asshole. I positioned his cock at the entrance to my tunnel and eased myself down on it. The fucking that I had taken earlier from Andy made it not too difficult to insert. I was still tight enough and hot enough to make Brian groan with pleasure.
"Am I in your ass sweetheart?" Brian whispered to me. I nodded. "God damn! I've never done that before," he added. I tried to move my hips and flex my ass cheeks just enough to not create a scene but still stimulate the cock inside me. It was working and in short order Brian was filling my bum with his liquid love. I was ready to excuse myself but David, sitting next to us, had already taken out his big cock and was pulling me to his lap.
I repeated the lap dance, getting my bum fucked again as I ended up doing for all four of the men. During my last lap dance with Martin, I felt Richard slipping something into the top of my stocking. I didn't bother checking to see what it was at the time. By the time Martin at the end of the line was finished blasting his cum inside my worn out rectum the bouncer of the club was standing next to the table. The large, muscle bound man did not looked pleased.
"Ma'am, I'm afraid I am going to have to ask you to leave," the bouncer, with his chiselled face framed by a brush cut, informed me. He must have thought I was a hooker. The guys looked a bit embarrassed and quickly scattered from the bar. The bouncer escorted me out the back way so not to disturb the other guests. As we stepped outside into the back alley the burly man said, "Sorry lady, not my idea, the manager made me do it. It looked like a lot a fun to me. No hard feelings hon?" He was smiling. I smiled back and grabbed hold of his crotch. His cock was already stiff as iron.
"Well, at least one hard feeling," I answered. He paused, and then undid his pants, releasing his tool.
"Ok lady, make it quick, I gotta be back before I get in shit," he told me very business like. Suddenly, I was a whore. I found myself kneeling in the dirty ally, giving a blowjob to this guy who just threw me out of the club. There was no romance involved. He held my head in place and fucked my face as fast as he could. He took fast hard stokes at my mouth. I was choking on many of the thrusts but he didn't care. In five minutes he spurted his load down my throat. He didn't give me any choice about swallowing or not. He had a firm grip on my head as his balls pressed against my chin. It all went down. Then he was gone, back into the bar. I was still kneeling there, catching my breath. I felt so cheap, but only for a minute. I found the item that had been slipped into my stocking. It was a roll bills adding up to five hundred bucks.
"So, I'm a whore!" I announced to Kelly as I entered the room. Kelly's date had left a little earlier. My wife was lying on the bed, wearing a tiny black teddy, waiting for my return. She demanded to know the details and I told her everything. She was excited to hear about it and when my story was over she told me to climb on top of her and sit on her face. Kelly eagerly ate my ass out for the next hour while I watched the video of her and Amy making love.
The next morning we agreed that things had got out of hand and we needed to take a step back. We didn't have any more excitement like that for the rest of our trip. When we got home we decided to go back to our one night a month theme night but we added another day to our monthly rotation. We haven't got a name for it, but I dress up as slutty as possible, Kelly takes me down town and drops me off in party district while she heads to local 'ladies only' club. The next day we share the details of our respective adventures and add up the money I come home with.