A gay story: A Question of Sex About eighteen months ago I was at the airport on my way out of town on yet another business trip. Even though it was a little less then an hour prior to flight departure I was surprised at how few people were in the boarding area, especially since it was midweek and this was one of the last two flights to Houston for the day.
Taking a seat in one of the uncomfortable hard blue plastic chairs I took out my paper and began to catch up on the news. I’d been reading for about twenty minutes when someone took a seat across the aisle from me.
When this person sat the first thing I noticed was they were not unattractive, but there was something else about them too, but what?
Casting a glance their way every now and then, catching glimpses, I casually studied them but just couldn’t get a hold of it. Folding my paper to watch this person surreptitiously I realized after several minutes what I couldn’t quite put my finger on was that it was difficult to determine whether they were male or female.
The mannerisms with which they moved suggested female, but not definitively. This person was very slender, about thirty or thirty-one, not very tall, around 5’6″, had blond hair hanging to the jaw line on the sides and just touching the shoulder towards the rear, but not really cut in a fashion to denote sex. The clothing was nondescript, black pants and jacket and a white shirt. I looked at how the shirt was buttoned and saw it was left over right, a man’s shirt, but again this wasn’t definitive proof of sex. They wore no jewelry, no make-up, no nail polish and nothing could be decided on the shoes being worn because they were deck shoes.
This evaluation took all of three or four minutes and I could arrive at no determination from it. So I gave up trying to decide the issue and went back to reading my paper.
A minute or so later Blondie asked “excuse me, when do you think we’ll board?”
After looking at my watch I responded “it’d probably be another ten minutes or so.”
Blondie’s voice brought me back to the quandary, but hearing the voice didn’t help in determining sex either; it was smooth, soft but husky, like Lauren Bacall’s.
Looking at Blondie as we spoke; those eyes, the eyes were definitely feminine, and a deep green; Emerald green if I had to define them.
Blondie stood, stepped across the narrow aisle and took the seat next to mine then asked almost in a whisper “do you mind flying?”
“It doesn’t bother me, I fly a good bit” I said.
Blondie looked out the window to the plane sitting at the jetway and said “I’m not real comfortable with it, I don’t fly often and only when I have to.”
Seeing Blondie was frightened I suggested “then why don’t we talk about something else so we don’t dwell on the subject.”
Blondie smiled weakly and said “maybe that’ll help take my mind off it, thank you.”
Dropping the paper onto the seat on my other side I extended my hand and introduced myself and with a genuinely friendly smile Blondie took my hand and said “I’m so glad to meet you, my name’s Dale.”
We shook hands while in my mind I exasperatedly screamed “oh come on!! Dale!?!” A non-gender establishing name, the androgyny of this person was maddening.
But the hand I took was soft, smooth, gentle and had a firm grip; I’ve had a thousand similar handshakes from both men and women over the years. As we shook hands I added “a pleasure to meet you too” to our introduction.
Since I have to refer to Dale as something other then “this person” or just “Dale”, we’ll use the adjective “her” based solely on her mannerisms and my impressions so far. That being said I still wasn’t a hundred percent sure of Dale’s sex.
Dale asked “traveling on business?”
“Yes, on my way to Houston. And you?”
“Houston too, then on to Denver tomorrow.”
“Business as well?”
Dale nodded and said “yes. Well teaching actually. I’m an educator, a culinary educator.”
“And you were teaching here in town?”
Nodding again she said “hmm. I was teaching at the local affiliate of the culinary school I work for.”
“And now you’re leaving, going home?”
“No not yet. It’s on to Houston this afternoon and tomorrow I’ll meet up with two other teachers who are coming in on a mid morning flight from Santa Fe and then we’ll all catch a midday flight to Denver.”
We spoke about her work for the better part of the remaining time we had before boarding and apparently being a culinary educator was a big deal, being several big steps up the professional ladder in this field. To be a culinary educator she had to go though several stages of training and be able to demonstrate certain expertise in each stage to reach the level of being a certified chef, which she was and being able to teach the culinary arts. I was impressed.
Booming over the speakers in the mostly empty boarding area the gate agent announced they were ready for boarding and since there were only about thirty passengers for this flight everyone could board at this time.
Dale and I rose from our seats together and shook hands then I said “it’s been a real pleasure talking with you, albeit for far too short a time.”
Dale responded with a smile “well, I did stop thinking about the flight. Thank you so very much.”
We boarded and took our seats and once we’d taken off the flight attendant announced since we were so light the passengers could sit wherever they liked.
Once in the air I’d leaned my seat back, closed my eyes and was thinking through some items for the meeting the next day.
A few minutes later we hit a little turbulence and had a couple good bounces but then things settled down again. A minute or two later the captain came on the speaker and said we’d hit an unexpected pocket of turbulence but didn’t expect anything more as he’d been given permission to change altitudes.
A little after going through the rough weather I had the feeling someone was watching me so I cracked open one eye and saw Dale standing in the aisle with one elbow on the back of the seat in front of mine, fingers of her other hand pulling at her bottom lip, looking down at me.
“I’m sorry, did I wake you?” she asked her voice quavering.
Seeing her condition I pressed the button to raise the seat, smiled and said “no I was just thinking. Why don’t you sit down here next to me.”
Taking the inside seat she asked “I was wondering how you could sleep though something like that.”
Smiling I said “that wasn’t so bad. And besides what could I do about it, I’m just along for the ride.”
Dale looked at me as if doubting my sanity so I asked “so, you were telling me about your work and teaching.”
As she talked I studied Dale’s face looking for any clue that would give a hint to her true sex. Her face and eyes were truly feminine with high cheek bones and those amazing emerald green eyes I’d mentioned earlier. There was no hint of a shadow on her face, no suggestion there was any hair at all or that the face had ever been shaved. Her mouth was full, lush and sexy with slightly puffy lips. The neck was long with no hint of an Adam’s apple, but again that’s not proof of sex, I don’t exhibit one myself.
I looked at her hands. They were soft and smooth, long fingered, very feminine, but again nothing that would provide a categorical answer.
Downward glances revealed no hint of breasts but that could have been because she was small breasted and the way the shirt hung loosely on her. I knew no more now then I did before.
We talked about our work for the remainder of the flight and just before they announced our final approach to the Houston airport Dale asked “where are you staying?”
“The Airport Marriot.”
“Me too” she said.
I asked “well then would you like to get together for dinner after we check in?”
Dale smiled and said “I’d like that.”
“Good. I’ve only got my carry on with me, you have any baggage checked?”
“No, just have my carry-on.”
After parking at the terminal we deplaned and walked together through the terminal. Dale walked out in front of me once or twice and I noticed the way her hips swiveled as she strode, very nicely I must admit, but a very feminine stride.
Dale asked “where do we catch a cab?”
“Cab?” I echoed.
She questioned “how do we get to the hotel?”
“Well there’s a tram that runs from terminal to terminal and also stops at the hotel.”
“Really?” she asked then added “well that’s neat, isn’t it.”
We went downstairs to the tram station and took the three minute ride to the Marriot. Exiting the tram we rode the elevator up to the hotels lobby.
There was one person in front of us at check-in and only one clerk working so I thought I’d have an opportunity to hear how the clerk addressed Dale and get a clue or maybe even an answer to Dale’s sex.
As we waited for the clerk to call for her to check in I asked “it’s seven o’clock, how about we meet here in the lobby about seven forty-five and then leave for dinner?”
Nodding Dale agreed just as the clerk called “next.”
I motioned for Dale to go ahead and stood waiting next in line just behind her listening as the clerk asked “how can I help you?”
Dale had given her name and the clerk was typing in her computer when a second clerk further down the counter came out from an office and asked “may I help you down here sir?”
I moved to the second clerk’s station and began the check in process while trying to eavesdrop on Dale, but was out of earshot and could hear nothing.
As I’m a regular visitor check in went quickly for me but Dale was still working with the clerk.
I walked to the elevator bank and pressed the button then stepped back and looked over at Dale and could see she was having a very animated conversation with the clerk. Her posture, the way she moved her hands, the look on her face, the way her jaw was set I could see she must be having some difficulty, but it also occurred to me these motions bordered on being masculine. I was considering going over to help if I could when the clerk nodded and placed the registration form on the counter top for Dale’s signature.
The door opened just then and I stepped onto the elevator and as it rose to my floor and I walked to my room I thought about the asexual appearance and mannerisms of Dale.
As far as I was concerned Dale’s true sex was irrelevant since I’m bisexual, but not knowing positively was kind of fun, almost a game. And what’s more there was no reason to think anything we’d done so far or dinner tonight would lead to sex and realized I may never find out anyway.
Entering my room I undid the Velcro straps that held my small computer bag to the carry on and placed it on the desk. Then after pushing the tow handle back down I tossed the carry-on onto the luggage caddy and opened it, removing my toiletry kit, a fresh shirt and a sports coat.
I stripped off my shirt as I walked to the bathroom and took care of some business then went to the vanity and washed my hands and face. I brushed my teeth and applied some fresh deodorant and cologne before putting on the clean shirt. This had all taken about twenty minutes and still had about fifteen more before I had to meet Dale downstairs.
Sitting at the desk I took out my cell phone and called my wife to let her know I’d arrived safely and was getting ready to go out to dinner with a friend, only a half-lie.
I can admit and freely acknowledge my wife is much too good for me and I don’t deserve her in my life. With the exception of a few years when we were first married my failing has always been my fidelity, and although I know some would consider this a contradiction, I do love her deeply.
I don’t feel guilty about my playing around, not at all, but when, please note I didn’t say “if”, the day comes and she confronts me about it I’ll deserve whatever she says or decides to do about it.
She’s also unaware of my bisexuality, although she may have suspicions about that because our personal sex play includes her regularly using various toys to fuck me.
We chatted for several minutes then I told her I loved her and would call in the morning then ended the call. Grabbing my sports coat I left the room and headed back down to the lobby.
It was about seven forty-eight when Dale stepped off the same elevator I’d rode down which indicated she was staying in the tower too.
As we walked across the lobby towards the exit I asked “so, what are you in the mood for?”
Dale thought a second then replied “well we are in Texas, how about steak or bar-b-que?”
When the cab pulled up Dale slid in first and when I’d closed the door she moved back beside me. Telling the driver the name of the restaurant we settled back and talked quietly for the ten minute ride.
At the restaurant the hostess sat us immediately and as we looked over the menu the waiter asked “and what would you folks like to drink?”
Dale said “I’m not sure yet, give me a minute please.”
“I’ll have a single malt scotch.”
“Tobermory?” the waiter suggested.
“That’s fine.”
After writing down my order the waiter paused a few seconds before asking Dale “and have you decided miss, or would you like to wait until I come back to order?”
Dale though another moment then said “I’ll have a double bourbon neat.”
Quite a drink for a lady I thought, but also noted the waiter had thought Dale was female. And as we spent more time together I found myself leaning more towards Dale being female too.
As we ate we talked and Dale said “I’ll be glad to get home again, I’m so tired of being gone.”
“How long you’ve been gone?”
“Six weeks by the time I do get home.”
“Quite a while to be on the road.”
Nodding she said “yeah it is. I taught at the school in New Orleans for a month and I’ll be in Denver for two more weeks before heading home.”
“Where’s home and work?”
“I live in Danbury, Connecticut and commute to New York for work.”
“Quite a ride.”
“That it is, but its way too expensive to live in the city.”
We talked about where she lived and worked for several minutes then I said to her “you sure don’t sound like you’re from New York or Connecticut; you sound more like you’re from the Midwest I’d say.”
“I was born and raised in Detroit” she said as she sipped from her drink. Placing the glass down, she sat forward in her chair and perkily said “a little trivia.” Then more calmly “if you’re standing in Detroit and began walking south what’s the first foreign country you’d come to?”
I thought a moment then said “Canada.”
Sitting back now she said “wow, you know your geography. Not many people get that one. Most people usually say Mexico or Cuba.”
Smiling I jokingly replied “yeah and I read and write too” and she laughed in that husky voice of hers.
We finished our meal and asked the hostess to call us a cab while we waited in the bar. We had another round as we waited and once the cab arrived we went back to the hotel, Dale sitting right next to me again. Exiting the cab she insisted on paying the fare since I’d covered the first ride and dinner.
Turning back to me after paying the driver she slipped her arm through mine and looking up at me with those green eyes asked “would you like to come up for another drink?”
“Sounds good” I replied as we entered the lobby and walked towards the bank of elevators.
As we crossed the lobby I heard someone call out “hey, Bill!”
I turned and saw a friend of mine, George crossing towards us. Wearing his ever present wide grin George walked up saying “I’ve been looking for you all evening, thought I’d missed you.”
We shook hands and then introduced him to Dale.
“Nice to meet you little lady and if you don’t mind me saying it them some dangerous eyes you have there” and took her offered hand.
Dale giggled and said “oh, but you are the flirt aren’t you.”
Now even though George has lived in New Jersey for many years, he was born and raised in Texas and still dressed as if he lived here complete with cowboy boots, hat and the requisite 4×4 belt buckle and the way he said “little lady” to Dale is just the way he talks and flirting is second nature to him.
But notably George’s impression was Dale was a woman and this carried some weight with me as you see George is a bit of a world class pussy hound.
George and I have been friends for more then fifteen years and he honestly missed his calling not being a salesman. He is one of those individuals who was born with the gift of gab and can talk just about anyone into or out of anything. He can convince you to sell him something you really wouldn’t want to sell, then turn around and sell it back to you at a profit.
For example once we were in Chicago together and doing some club hopping. At the time I’d been carrying on a long term affair with a woman named Candy. She was President and General Manager of a company which was involved in the same business that I was in and as we attended many of the same industry meetings and seminars it afforded us many opportunities to get together out of town.
Anyway Candy, George and I were in a club and George picked up this brunette and she joined us as we bar hopped. In the third or fourth bar we’d been to George excused himself and went to the restroom. He returned about ten minutes later with another woman, a blonde, in tow and when they sat the brunette got pissed and stormed off.
George told the blonde “sit a minute honey and talk to my friends, I’ll be right back.”
Candy and I chatted with the blonde and amazingly George came back five minutes later with the brunette. We all sat and talked, George giving both of his girl’s equal time, smoothing things over and when we left the bar about ninety minutes later to head back to the hotel they both came with us. We spent another forty minutes or so at the hotel bar before Candy and I left them and headed to her room.
The next morning when I’d met George at one of the meetings I asked “so how’d it work out last night?”
George smiled and said “fantastic.” He added “we had a threesome and I talked them into fooling around together although they both said they’d never done anything with another woman before. They really got into each other and after awhile I just sat and watched. Let me tell you these girls were fucking hot. We had breakfast together this morning and then I put them each in a cab home.”
All I could do was smile and shake my head as he looked at me smiling also and ask all innocent-like “what?”
I didn’t doubt his story in the least because we’d shared other women or had been involved in foursomes together before. Unfortunately for me George is straight so nothing has ever happened between us other then a little cock to cock action once as we both fucked this one gal in her pussy at the same time.
Now back to this night in Houston. After he’d mentioned he’d been looking for me I asked George “did I forget, were we supposed to meet this evening?”
He said “no, but some of us are just heading out and wanted to see if you’d like to come along too, do some club hopping. And please bring your friend along too.”
Looking at Dale I could see in her eyes she didn’t want to go out again so I replied “no, I think I have some work to do here”, adding after a pause “for tomorrow’s meeting.”
George didn’t miss a beat, smiled knowingly and said “ok, I’ll see you tomorrow then.”
He shook Dale’s hand again saying “it was nice to meet you Dale” then shaking his head as he continued to hold her hand added “girl, them are some eyes” then he left us standing alone.
George and I have chased a lot of skirts together so he knew the score.
Waiting arm in arm for the elevator to arrive I looked at Dale who had been staring up at me so I leaned over and kissed her. I felt her tongue dart across my lips before we broke apart hearing the “ding” announcing the elevators arrival.
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.