A Question of Sex

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As the doors slid closed we embraced and shared a passionate kiss as the elevator rose. Still embracing after our kiss Dale said in a whisper "I don't have any condoms."

In the same voice and tone I responded "you act as if you think we're going to have sex."

Dale pulled back with an almost startled look on her face and saw I was smiling and knew I was kidding and just as eager as she was.

She slapped me on the arm and smiling said "creep."

I pulled the room key card from my pocket and said "I've got what we need in my room" and after a pause of the proper length to denote at least some faux reluctance she nodded. I pushed my key card into the slot on the button panel and pushed the button for my floor.

Dale looked at me questioningly and I explained my room was on the concierge level and you needed the right kind of coded key card to get the elevator to stop on that floor.

We walked to the room with my arm around her shoulders and hers around my waist. Entering the room we again embraced and engaged in the most passionate kiss of the evening so far.

We parted and Dale walked further into the room as I took off my sports coat and hung it up, and she removed and dropped hers onto the back of the desk chair.

Dale was looking out the window as I walked up behind her and wrapped my arms around her and kissed and nibbled her neck. Dale leaned back into me and laid her head to one side, exposing her neck to my lips.

After a minute or so I sat on the love seat and Dale straddled my legs and knelt facing me, sitting on my thighs. We engaged in more kissing our tongues in a fierce battle as I ran my hands over the outside of Dale's arms and shoulders and down her sides to her waist.

After making out for several minutes Dale leaned back, unbuttoned her shirt, pulled it from her waistband, shrugged it off her shoulders and dropped it onto the floor at my feet.

We'd maintained eye contact as she'd removed her shirt and we kissed again after she'd dropped it, my hands running up and down her back. And this time as I caressed her body my hands moved lower, moving over her hips and ass feeling her through her pants.

Again Dale leaned back, placing her hands on my knees exposing her nude upper body to my view. Dale had no breasts to speak of; just nipples and they were erect, dark, long and thick, almost as long as the first joint on my little finger and her left one was pierced with a small diamond hanging from the jewelry she wore in it.

Dale moaned as I passed my finger tips over her nipples, causing them to flip up as my fingers moved over them. Running my hands further down over her flat belly I saw she also had a pierced navel, a Dolphin pendant hanging from the belly ring, all very feminine.

Bringing her mouth back to mine Dale placed her hand down between us cupping my crotch, feeling my erection through my clothes as we kissed.

Things were moving along nicely but I had to stop before we went too far to stop.

I hadn't bathed since I'd gotten up this morning at five-thirty so when our mouths next parted I whispered to Dale "I need to shower, join me?"

Dale nodded and hopped from my lap, leaned over and kissed me a quick one then walked towards the bathroom.

I waited until I'd heard the shower start as Dale adjusted the water temperature. Then I got up and went to my bag, dug through it, took out several condoms and placed them on the bedside table. Sitting on the edge of the bed I removed my shoes and socks, stood and dropped my pants then padded into the bathroom too.

There was no tub in this room just a large shower with frosted glass on two sides. Dale was already in the shower as I removed the rest of my clothes and looked at her body through the opaque glass as she let the water run over her, her back to me.

I glanced down at the small pile of clothing Dale had dropped onto the floor and unless they were under the pants there were no panties or underwear of any kind in view.

I opened the hinged shower door and stepped in, it closing with a click behind me as I stood by the wall. I admired the view of Dale from behind, the softness of her body, the way her hips flared from her narrow waist, the round smoothness of her ass, the long, thin, shapeliness of her legs.

With a worried look on her face Dale glanced over her left shoulder at me without turning her body and in that moment I knew, I knew Dale's sex.

Softly I said "Dale, turn around for me."

Dale didn't move other then to lower her head.

I said quietly "it's alright, I know. It doesn't matter, turn around and let me look at you."

Again Dale gave me an over the shoulder look then slowly turned to face me while we maintained eye contact.

I looked into Dale's eyes for a moment more then moved mine slowly downward until they arrived at the definitive answer to Dale's sex.

Dale was shaved and below this bare area hung the sweetest little cock I'd seen in a long time. Dale was cut and soft it was about two inches.

I stepped forward and took Dale into my arms and kissed him again, passionately.

Dale responded hesitantly and a little tensely at first then with building passion, placing his arms around my neck.

Taking my mouth from his I looked into his still worried eyes and smiling said "relax; it really doesn't matter."

"When did you know?"

"Not until you looked over your shoulder at me a moment ago. The look on your face gave you away."

Stepping back I took the bar of soap from the tray, unwrapped it and while using it to soap his chest went on saying "all evening, ever since you sat across from me at the airport I've been going back and forth in my mind on whether you were male or female, I just couldn't decide."

Dale took the soap from me and began to wash me and said "your friend thought I was a woman."

"I know, so did the waiter at the restaurant, but I was never sure. And let me tell you it's quite an accomplishment to fool George, and wouldn't he flip knowing how wrong he was."

"And it doesn't upset you that I'm not a woman?" he asked.

I soaped my hands up while looking into his eyes and after placing the soap back in the soap dish I looked down and took his soft cock in my hands and while cleaning it said "no, I found your androgyny somewhat intriguing. And now the issue is settled I still want to be with you very much." Looking back up and deeply into his eyes repeated softly "very much."

After that we finished washing each other quickly and stepped out of the shower, dried and fell onto the bed kissing. Dale lay on top of me grinding his cock into mine as my hands moved up and down his back and over his smooth ass.

We made out for several minutes before he began to slide downward stopping to lick at my nipples, his hand cupping my balls working his fingers to massage them, rolling them.

After licking each nipple Dale moved down to my cock and held it in one hand as he licked up the shaft from the base. He took the head of my cock between his lips and ran his tongue over and around the head before swallowing me. Holding the base of my cock Dale's mouth began to move up and down on me as he held my balls in the palm of his other hand.

He wrapped his thumb and forefinger around my scrotum squeezing my balls into a smaller sack, much like if I were wearing a strap. As he continued to bob his head on my member he began to gently tug downward on my sack and I was experiencing these wonderful feelings as he pulled and released my constricted balls.

Dale's puffy lips felt amazing as they moved up and down my cock and at the end of each upstroke my cock head would pass through those lips and they'd pause just a second against it, pursed as if in a kiss before they parted, sliding downward over my cock again.

I was only able to take about five minutes of this fantastic head from Dale before I had to ask him to stop. Dale moved back up my body and again lay atop me as we kissed for another minute or so, his knees on either side of me as I cupped his ass.

Rolling Dale off me onto his side we kissed for a bit more then pressing against his shoulder I urged him onto his back.

I slid down and took his almost female-like right nipple between my lips and flicked it with my tongue and heard a moan of satisfaction from him. As I licked and sucked this nipple I played with the other as Dale's hand caressed the back of my head and neck, his fingers moving through my hair. After a couple of minutes of making oral love to his nipples I moved down his body and lay beside him looking at his cock.

He was soft but wet with his precum from having been erect earlier. He leaked precum but not nearly as much as I do when excited. He was cut, about two inches and it stood upright but leaning slightly to one side.

I ran my finger through the precum that was pooled in a little crease at the base of his shaft and with that lubed finger I lightly ran the fingertip over his cock and teased the head as it slowly began to lengthen and harden.

When fully erect it was a nice six inches with a flared head and I spied another dollop of precum as it dribbled out of the pee hole and with the tip of my tongue I licked it up and savored the taste.

Wanting more I took his cock into my mouth and began to go down on him, his shaft sliding between my lips. On the upstroke I held the head between my lips and swirled my tongue over it before swallowing him again. I bobbed my head and played with his balls for about five minutes when Dale stopped me because he wasn't ready to cum yet either.

Dale spun around and we lay head to head, our feet in opposite directions and kissed for a bit before moving into a 69. I didn't suck Dale at first wanting to give him a moment to calm down but he sucked me back into his mouth as I held his cock and played with his balls.

After a minute or two I rolled onto my back pulling Dale over me as I did and took his cock back into my mouth.

Dale fucked my mouth as he went down on me his hips moving up and down as his cock slipped back and forth between my lips, my hands on his cheeks.

Looking up I see for the first time Dale's asshole and mentally shake my head. His asshole was a puffy edged, slightly red long slit and almost had the appearance of being a pussy, bringing the androgyny of Dale full circle.

I rubbed a finger gently over the edge of Dale's rear hole and it contracts and relaxes to my touch. Dale's rhythmic fucking of my mouth changed to a slower pace as I stimulated his asshole.

A minute later he rolled off me and the bed then leaned down and kissed me and said "I'll be right back."

He was gone less then ten seconds when he handed me the little bottle of complementary hand lotion from the vanity then got back as he had been.

Our cocks back in each others mouth I opened the bottle and shook some out onto his ass. Using my fingertip I used the lotion to lube Dale's hole, pushing my finger in to the second knuckle. As I push more lube into him I add another finger and Dale responds by uttering short, sharp, moaning grunts onto my cock and rolling his hips as I finger fuck his hole.

After several minutes of this play Dale rolled off me and sat with his legs curled under him. He reached for the bottle of lotion and poured some onto his hands and worked them together spreading it. He straightened his legs out towards me and rolled onto his left side as he brought his left knee up towards his hip keeping it flat on the bed.

With his lubricated hand he began to play with his asshole pushing three fingers into himself right off. After a minute he added the fourth finger and his thumb then pushed them all into his asshole to the third knuckle. He pulled his hand out until just the tips of his fingers were left in his hole, his hand and fingers looking like a wedge, then pushed them all back in.

After another minute's play he took his hand out and wiped it on the towel we'd dropped by the bed, tore open a condom package, scooted over and unrolled it over my cock.

Next he knelt over me holding my cock aimed at his asshole and then sat on it. I slid in easily, Dale taking me to my balls all at once. Sitting flat on my hips with my cock buried in his ass he moved his ass in a tight little circle while holding himself up with his hands on my chest.

He began to rise and fall on my cock as I played with his extended nipples. Using his legs and arms he lifted his ass until my cock was barely in him then slammed back down onto it again.

We fucked like this for maybe four or five minutes when I said "let's change positions."

He slid his ass off my cock and lay on his back across and on the edge of the bed with his knees pulled to his chest.

I walked around from the opposite side of the bed and stood in front of him at the edge and entered him again.

I held his legs with my hands on the back of his thighs as he played with his nipples. I watched as his semi-hard cock swayed back and forth, precum bubbling out of the head as I fucked into him.

After six or seven minutes I was getting close to cumming when he said "how about another change of position?"

I nodded and backed off, my cock slipping from his asshole and hanging down still hard. As Dale got off the bed I squeezed hard against the base of my cock, a method that for me always helped in delaying my cumming.

After getting off the bed he leaned over the desk in front of the window after moving the chair aside. His feet were spread wide and he looked back at me and said "fuck me."

Moving behind him I rubbed the condom covered head of my cock up and down over his anal opening before pushing back in. Holding onto his hips I fuck my cock in and out of him as he laid flat across the table.

As I pushed into him he said through ragged breaths "harder and faster" and I began to slam my hips against his ass and increased the pace of my thrusting.

It took only about three more minutes before I was on the verge of cumming and Dale must have sensed this as he suddenly stood pulling his ass off my cock again. He turned, squatted and ripped the condom from my cock and held the head pointed at his mouth just as I began to shoot. His aim was true as most of what I spurted went into his mouth.

My cock done spurting, there was a thick inch and a half long drip of cum hanging from my piss hole. Dale lifted my cock higher and with his head leaning way back, waited until it dropped into his wide open mouth then passed his tongue along the bottom of my shrinking shaft until he took the head between his lips. He held it in his mouth for only a few seconds before releasing it.

Dale swallowed everything he had caught in his mouth then stood, put his arms around my neck and we kissed my arms around his waist.

As we kissed I lifted him up and sat him on the desktop then pulled the chair back over and sat on it between his wide spread legs.

He leaned back on the palms of his hands, his feet on top of my legs as I went down on him again. As I sucked he moaned and made little sounds of contentment, sounding not unlike a woman would.

I'd sucked him for three or four minutes when he began to hump his hips, saying, almost whining "oh Bill that feels so good, don't stop, suck me, suck my cock" as he neared his nut.

I moved my mouth up and down his length and when his body language told me he was going to cum I held his cock in my mouth swirling my tongue around its head as he shot his load, swallowing what he gave me. After his cock finished pulsing I looked up at him and smiled then kissed his softening cock head.

Standing I stood between his spread legs and took him into my arms again as we passionately kissed for a minute or so before picking him up from the desktop, turning and lying him on the bed. I crawled in next to him and we cuddled, spooning, falling asleep together.

We slept until about five-thirty in the morning when we got up and showered together then dressed.

In spite of knowing the truth I couldn't help but notice that even in the rumpled clothes from last night Dale again looked more feminine then masculine.

As we stood together kissing I asked "care to have breakfast with me?"

Dale thought a moment and said "very much. But I'd like to go to my room and change first."

Kissing him again I said "don't be long."

Dale asked "fifteen minutes?"

I nodded and said "we'll meet in the lobby."

Dale picked up his jacket and threw it over his arm, walked to the door and with his hand on the knob stopped and hesitated before pushing the lever down to open the door. He stood with his back to me for two or three seconds before turning halfway around and looking back at me said "I'll understand when we get downstairs when you refer to me as a girl. In fact I prefer it that way. I know how I look and like that people think of me that way."

Nodding in reply was the only way I could think to respond and then Dale left.

We met in the lobby fifteen minutes later as we'd arranged and walked into the hotel restaurant and had breakfast.

George and another colleague joined us shortly after we'd sat and we all enjoyed our breakfast and conversation, laughing to one after another of George's stories.

When we'd finished our breakfast I walked Dale back to the elevators and as we hugged Dale whispered into my ear "thank you. You've been the best time I've had in quite a while."

I responded "I appreciate that but believe me, the pleasure was all mine" and we kissed one last time.

The elevator announced its arrival and I watched as he stepped into the car and then door closed and Dale was gone.

George walked over and put his hand on my shoulder and asked "so, how was she?"

Staring at the closed door I thought a moment, gave a short one syllable ironic laugh and replied "Dale was more then you'd think, a little different but a lot of fun and very good company."

George slapped me on the back and said happily "well partner, isn't that the way it's supposed to be."

I was in New York about eight months ago and went to the restaurant where Dale worked but he wasn't in that night. I asked the manager if I could leave a message for him and wrote out "sorry I missed you tonight, understand you're in Toronto. Please give me a call when you get back" and wrote down my number.

I've yet to hear from Dale. The manager struck me as someone who'd keep their word so my guess is its Dale's choice not to call and I can accept that.

Perhaps when I get back to New York again Dale will be in should I call at the restaurant. Perhaps this time I won't ask for him and see how it works out.

But regardless I'll always remember Dale if for nothing else, for the uniqueness of being an individual.

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8 Comments
AnonymousAnonymousover 3 years ago
Just okay!

I expected a little more detail on the fucking and seduction of this transvestite. Some parts were fine but this story drug on too long. Hopefully you'll meet Dale someday and give the slut the fucking he deserves. You should let your wife in on your secret. Who knows, it just might turn her own. Then the possibilities are endless.

TheSecretPervertTheSecretPervertover 12 years ago

That was very interesting. I had fun reading it.

AnonymousAnonymousabout 13 years ago
So HOT

Loved the whole story. Not Pushey, Just Hot NIPPLE and Hot Cock Sex. Thanks from a Nipple and Sweater Lover.

Greyfox69Greyfox69about 13 years ago
Great story

Definitely a great story. Keep on writing!

AnonymousAnonymousabout 17 years ago
I liked the story

I liked the story. The sex was totally hot!! I`d love to meet Dale myself, it seemed that he was a fantastic fuck!! The size and shape of his asshole intreged me also. I`d like to give it alittle tongue action before sticking my cock into it!! And I`d like to have Dale fuck me too!! Nice!

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