The flight finally ended at the Midwestern city that was my destination after and interminable number of stops in every town in Pennsylvania, and Ohio. Guess the flight was cheaper that way, since my employer was notoriously cheap in that when it regards the comfort of its employees. At least my baggage arrived with me. Retrieving my luggage headed for the designated meeting area looking for my ride to the company meeting.
In the crowd I saw a familiar face, it was Lenny our rep in LA, with a girl. As I approached it turned out it was not a girl but a small guy. Lenny’s companion had longish blond hair, a slight build not over 5’6” and his whole person just screamed faggot. ‘Oh boy, have to be careful here, and stay away from him. Perhaps late at night after a lot of booze, would hit on him, but not here at the company meeting.’
Shaking hands with Lenny he introduced me to the newest member of the field force Sammie from LA. He was to be our new rep in the Iowa region. ‘Wait till the farmers get a load of him.’ I thought. His handshake was weak and feminine, and he smiled demurely at me.
Have to tell you we had to openly homosexuals on the staff, and there lives were made a living hell by the field force. Even a hint of such activities would open you to all sorts of problems. When our car arrived, I grabbed the front seat, claiming longest legs.
Well as meetings go there was nothing special about this one. You know how it is, the home office knows everything, and anything you do is wrong. As to Sammie, he must have been very lonely because he was shunned. The only thing exciting about the meeting was the VP avoiding answering the question on everyone’s lips: “Who hired that fag?”
It may have been part of a company policy to keep the troops guessing, but someone decided we weren’t working hard enough and the meeting should end a day early so we could get out there and produce. The girls in the back office scurried around making new reservations. My flight east was one of the first; so after a wild assed 70 mile ride arrived at the airport just in time for check in. The flight was canceled; have to wait until the morning. One of the rubber bands broke in the engine and they couldn’t find a replacement. After some hemming and hawing, they agreed to get me a room for the evening at an airport motel. I dragged my luggage out to the curb and headed for the motel. Now it is only five p.m., and am stuck for the evening with nothing to do, and there is always less than nothing to do at an airport motel.
After checking in and unpacking enough for the evening, put on a pair of jeans and a sport shirt and headed for the bar, intending to have a drink or two before dinner. Walking through the lobby to the bar, there is a disturbance going on at the desk, voices raised and all that. Looking over I see it is our new employee Sammie, he is crying and yelling at the desk clerk who is yelling back. So I have to do the right thing, going over to the desk in my best professional problem solver manner inquired: “Is there a problem here?”
Sammie turned to look at me: “Oh hi, they won’t let me have a room, and my flight home isn’t until tomorrow morning.”
“Is that right?” I said addressing the desk clerk.
“Yes, we are all booked up, and so is every other motel in the city, big race this weekend and lots of tourists.”
“Well let me ask you a question: If the President showed up tonight would you have a room for him?”
“Heard that one lots of times before.” Grinned the clerk, “The presidents in D.C. and we have no rooms, no hold backs, no cancellations, not even a broom closet, your friend is out of luck.”
Now then, what to do, what to do, a moral conundrum for me. Is this a test? “Sammie, I have a large room, you can have the other bed.” Turning back to the clerk: “Let me have the extra key to room such and such, and any extra charges give them to the airlines.”
So Sammie took his luggage up to my room and I headed for the bar, thinking a double would be good.
It was a good forty five minutes later and I was on my second gin and tonic, when someone touched me on the shoulder in a high pitched voice said: “Hi ya sailor you with anybody.” It was Sammie and everyone at the bar stared at us, or so it seemed.
Sammie hopped up into the bar stool next to me and ordered some brandy concoction. He had managed to rub against me, feel my thigh, and brushed his little ass against me in getting aboard the school.
Now if I had any convictions, I would have said to hell with what people thought and proceeded to welcome Sammie’s advances. I lacked those convictions.
There was some small talk about the meeting then he asked: “Just to thank you, let me buy you dinner.”
“I appreciate the offer Sammie, but the airlines is picking up the tab and I am just gonna have a hamburger and fries here at the bar.’ The lack of conviction wouldn’t allow me to go in the dining room with him, it would have looked too much as if we were a couple.
“Well that sounds good, you don’t mind if I just sit here and have a hamburger with you do you?” He asked.
“No, knock yourself out.” Luckily I thought, no one else from the company was here in the motel otherwise I would never live this down.
Sammie told me about his home in LA, where he had worked, and more information than I really wanted to know.
“Well what do you think of your new job?” I finally asked.
“Oh that, well I resigned today, it just isn’t for me.”
“You resigned, what happened?”
“This just isn’t for me, guess I am just a home body, the idea of being on the road two or three nights a week, didn’t really hit me until I got to this meeting. I miss my home, my friends. So I resigned.”
Well that cleared up one problem. Ordered another gin to wash down the burger and then the next time his hand brushed my thigh I put my hand on top of it. He looked at me and grinned.
A band started up about 9 PM and made conversation impossible, and I certainly wasn’t going to ask Sammie do dance. One of us not sure which, suggested taking a couple of drinks up to the room. The bartender did not give us a problem on fixing a couple doubles to go, you never know since liquor laws very so much from state to state.
When we got to the room, Sammie immediately went to the radio and tuned it to some local FM station that was playing soft music; you know the kind with a lot of strings, music to get it on by.
Setting the drinks down on the end table I sat down on the easy chair. This was going to be a bit awkward as to how to make the first move here. Most of my experience with men was furtive late night encounters, front seat blow-jobs, or being fucked in the back seat like a high school cheerleader. With these it was very easy to disassociate from the act itself. When you have your head buried in someone lap when you suck them off, you don’t really associate the dick you are sucking with the individual. If you are bent over in the back seat taking it up the ass, again it is easy to be cool and really just be some place else.
Tonight being cool was going to be difficult, not only was I in a room about to have sex with a man, but we would be sleeping in the same room afterwards. Hard to disassociate yourself from the act under these circumstances.
Sammie solved the first move problem by sitting down on my lap and kissing me. We sat like that for few minutes kissing and feeling each other up. He unbuttoned my shirt and sucked my nipples, then unbutton his shirt so I could do the same for him. He had small budding breasts. I was hoping his sex wasn’t going to be as small as he was.
I got his cock out after he unzipped his trousers, he didn’t wear shorts. Assumed he had done that when he dropped his luggage off. His sex was not stunted, his cock was about the same size as mine, and he hadn’t been circumcised. Leaning over I took him in my mouth and he let out a little groan as I rolled his foreskin down and sucked him.
This was a bit much considering there were two king sized beds in the room, so we moved to one of them disrobing as we did. We assumed a prone position we went back to kissing and playing with each other’s cocks. That didn’t last long; we changed positions again and began to suck one another.
Lying there with his cock in my mouth I decided for once to try and be in the moment. Enjoy his lips on my cock and enjoy eating him in return. Rolling the skin back and rimming him, he responded by sucking me harder and playing with my ass.
This continued for a few minutes, and as I concentrated on the moment I knew what I wanted. Letting go of Sammie’s cock I asked: “Sammie do you want to fuck me.”
“Sure honey, how to you want me to do you?”
Again we changed positions and kissed, I guided his hand to my opening. He inserted his social finger in me, I caressed his cock, wanting it to stay hard. He worked one finger deeply in massaging the opening, then two and spread me open. Responding to his fingers and pushing against them, as he finger fucked my opening. I was hard as a rock, his fingers explored me, my cock drww up tight against my body, scrotum tight as a drumhead.
Well if you are going to be in the moment and not disassociate, you can’t take it from behind. I rolled onto my back and spread my legs. Sammie moved around grabbed a pillow and shoved it under me. He had done this before. Then he kneeled between my legs and began to probe me with his cock. Relaxing as much as possible I reached down and guided his cock to the spot it wanted to be, then as he pushed in I pushed out, letting out a small moan as he slid into me. My cock shot a load of clear fluid as the cock hit the end of its length.
The sentiment of the population both hetro and homo is that when you have that desire to suck cocks and be fucked in the ass you also get the ability to be a great lover. Nothing could be further from the truth. Some people are good at sex and others are not, doesn’t matter who or what you are sucking or fucking. Sammie was good at it, he had no misgivings about what he was doing, he was an expert lover. His dick was the right size, not too big, not too small; it filled me nicely with out being painful.
You know the feeling when you have someone inside you, the pressure, combinations of other feelings. “Fuck me.” I whispered. Sammie leaned forward I embraced him and we went after one another. As he pushed in I pushed back. Guess that is the difference between taking it and fucking. Sammie was fucking me and I was fucking him right back.
I was in the moment and at the moment was the woman and little Sammie was the man. So for the first time in one of these encounter fully admitted what I wanted and submitted to my desires to be made love to and fucked as a woman.
We stayed at it for a good while; gin will do that for you. Then Sammie whispered in my ear that he was coming and doubled the stroke. Wrapping my legs around his ass I goaded him on with my heels to get in as far as possible. My ass seemed to take on a mind of its own, I squeezed his dick as hard as I could and he made little gasps as he shot his load into me. I swear I could feel his warm cum fill me. It was too much for me, balls emptied out and sort of glued us together. This had been my first orgasm as a woman.
He softened and finally with drew. It was late by this time and we were both tired from the meeting and travel. We left an early morning wake up call his flight was first. When the phone rang and he was dressing and leaving I pretended to be asleep. I was back to being cool and disassociating from the moment.
The next morning took my flight back east. Never saw Sammie again, and no one at the firm ever knew the little ‘fag’ fucked me that night.
The moral of the story is: ‘If you ain’t where you are at, you are nowhere.’
Just a reminder that this is fiction, however certain events did take place. This was well before the HIV/AIDS epidemic, such behavior these days without protection will probably kill you.