Sex with Someone I Used to Know

I didn't entertain many women when I was a sex worker. I wasn't anti-women, but it was a different time. Women didn't approach me often and I certainly didn't approach them.

Pretty much the only women interested were the kind that took the least attractive aspects of men and built them into a female's body. Butch and boisterous bitches that were a lot more trouble than they were worth, they could be rough and took forever to get off, and then acted like they cared that I orgasm too. (Like that was going to happen.)

They were also just about always lousy tippers even when I treated them to an Oscar worthy performance and acted disappointed that they hadn't turned me off men forever or something. All in all, not a fulfilling experience in terms of financial reward or job satisfaction.

I entertained a few couples over the years, but it was rare. After I was ripped off by a husband wife team, I got incredibly cautious. On the rare occasions when I said yes, it was because they offered a lot more for my time and usually recognized them from the local scene.

Even then, I was just about always sorry after I took the date. Maybe it was because we were in a very conservative place (Iowa), but it seemed like the trick was always about him and she was there because he wanted it. There was just never a spark or any enthusiasm on their part for me. No lust. It's not fun and even kind of depressing to have sex with a person who seemed like they didn't want to be there.

(To be clear, I never actually experienced anyone actually being forced to do anything, but a few of them looked like they would rather be anywhere else and were definitely not responsive or adventurous. It might have been worse than I imagine. I don't really like to think about it.)

Anyway, I knew there were a lot of lesbians out there and at least some of them were remotely feminine looking and sex positive. I'd met a few in my travels and had a little sister who was currently playing with boobs and boners, but I guess they could fill their dance cards without having to pay to play. It was just the way it was and I didn't overthink it. That was just how it worked.

The only real exception I ever met to the rule was a woman I went to high school with. Her name was Stacy and I guess she'd heard the rumors about what I was doing in my old hometown.

When she arrived at the hotel bar I was working in in a town about 100 miles south of the one we had both grown up in, I wasn't completely surprised. It wasn't uncommon for people from our little town to move to the slightly bigger small town that we referred to as "the big city." Also, the town was far enough the way that people coming here for a visit would stay in a hotel overnight rather than driving home. I'd seen people I had gone to high school with before.

When Stacy saw me, she looked like recognized me immediately and bee-lined over to me like we were old friends.

We weren't really. Old friends I mean. We had been in a few classes together over the years and been to a few of the same parties. I remembered her as one of "the straights" in school -- member of the student council, belonged, to clubs, stopped the boys at second base, etc.

She had been much less of a cunt to me than most girls who hung the student body crowd, so there was that. I guess I hadn't fucked her boyfriend or brother or whatever -- and she had even loaned me her homework once or twice so that I could copy it and maybe avoid an F in Algebra, and I had appreciated it at the time.

(I later got F'd by the algebra teacher anyway, when he too stumbled into a bar I was working. A story for another time.)

Anyway, I recognized Stacy the moment I saw her. Like all of us, she had changed a bit over the years. She hadn't changed her hair -- which was still butter blonde, long, straight and parted in the middle -- but she'd filled out a little bit in all the right places. (She had been a bit on the skinny side in high school.)

Stacy was well dressed in an evening dress that probably cost more than I did on an average evening, and she carried herself with a bit more confidence, but that ditzy smile was still there and that had been her trademark.

I don't remember how the conversation started. Your basic "look at you" and "imagine running into you after all these days" I'm sure, but soon enough it was time for me to ask what she was doing in town.

She went into the part where she told me she was a bank officer now and she was in town for a conference. I was impressed. We hadn't been out of high school that long. When I started to tell the standard lie about what I did (clerical work was my go-to, as no one cares to dig into the matter) she stopped me with a smile and a wink.

"Oh, I know what you do."

I looked her in the eyes just to make sure I knew what she had said. The look on her face convinced me she knew all right and I guess I wasn't surprised. Given my high school reputation, I'm not sure she'd think I'd changed that much anyway. But then she made it more intriguing.

She looked into my eyes. That "no bullshit, okay" look that you know you can't lie in the face of.

So I just nodded my head and said "A girl has got to eat."

She smiled back at me with that big silly smile but also a kind of twinkle in her eye.

"Yeah, that's why I was looking for you."

She smiled again at me and looked like we had somehow reached an understanding.

"Can we get out of here?"

She tossed down a $20 which was more than enough to cover the tab, and we were on our way before I even formed an opinion on what might happen next. I didn't see her as threatening and couldn't imagine a scenario where she was a cop or anything, so we took the short walk to my place which was above a laundromat a short way away.

We didn't talk as we walked. I didn't know where to start and wasn't sure I'd want to say it on the street anyway, and she wasn't volunteering. Soon enough we'd climbed the stairs and I had the door unlocked.

It was late fall and though no serious snow had fallen yet, it was already very cold outside. I kept my place pretty warm as I did a lot of my work in cars and trucks parked in dark parking lots. By the end of the evening, I frequently needed to defrost. Also, when a frequent john came by the warmth would encourage him to get out of his clothes and down to business.

We both started removing our jackets as soon as we had the doors closed. I hung mine on the hook next to the door and took hers for similar storage, but when I turned back from the task I realized that she had her back to me.

"Would you get that dear? I have so much trouble unzipping this thing." She was clearly asking me to help her unzip the back of her dress.

I won't say that it surprised me, as after a while you grow a thick skin, but I was still thinking there might be an alternative explanation. I pulled the zipper down, but added that the bathroom was down the hall, testing the assumption that perhaps her tight dress was one that needed to be pulled down rather than up so that she could pee.

I know she understood the test and in answer she dropped the dress top down where it caught on her hips but did not hit the floor. I remember thinking that her bra was very ornate. We didn't' have Victoria's Secrets yet back then, so something like this would have cost some cash.

She smiled at me then, as if she knew I was finally understanding, and slid the dress down to her ankles, where she stepped out of it.

"Your turn" she whispered. She gave me a look that gave me a bit of a chill down my back, which was something I never experienced with men at the time.

I guess, I must have looked just a bit reluctant though I was actually a bit confused.

Stacy picked up her purse and pulled out a wallet as if she understood.

"How much for an hour?" She smiled again. "Old friends rate of course."

I could tell she was looking for some reaction from me, and half expected she was mocking me, but I still didn't expect that if I took money there would be a vice squad knocking down my door. I named a price that was twice my standard hour and somehow wasn't surprised when she whipped out two large bills to pay the freight.

"Where's the bedroom?" she asked as she reached out and put her hand in my blouse. "I can't wait to get naked with you."

Well, this is happening was really my only thought on that.

Stacey followed my pointing finger and I followed her to the bedroom, still not yet quite sure what I'd signed up for. I noticed as she walked that her ass had gotten a little bigger though it was still in good form. Her shoulders were wide and well structured -- I remembered she'd played some basketball -- and in general the looked nothing like the type of woman who usually sought my services. Attractive really.

I won't say I was excited by it all, but I was curious to see how all of this was going to play out.

As soon as she entered the bedroom, she turned about that pulled me to her. Her hands were instantly on my ass and her tongue was just as suddenly in my mouth.

If she had been a man, I'm sure I'd have been doing everything possible to wiggle out of the situation -- I'd suck a dick but I wasn't much on tongues usually -- but for her it worked.

She stepped back eventually and kicked of her heels and dropped her underwear. She'd gotten her bra off without my even noticing, which was a good trick. Since I know people want to know these things -- she was about 5'7" and still around 130lbs or so. Still thin with little B cups and yellow blonde pussy hair to match her hair up top. (It was parted in the middle too, now that I think about it -- just from the bottom instead of the top.)

She motioned for me to lose my blouse -- I still had all my clothing on but now it was time to dress for work. When the bra came off she gasped a little bit as my boobs really were my best feature. As I stripped off the rest, she looked on, giggling a little bit at the various laundry dropped.

When I was done, she gave me a good look, her eyes as full of hunger as any man I had ever been with.

She motioned for me to turn around and put the rest on display, which I felt like she'd paid for.

"Fuck, you still have that tight little runners' ass. How did you keep that? I'd have thought all the boys would have torn that to pieces by now."

I didn't know what to do next, so I just stood there. She moved herself up and completely onto the bed, spreading her legs and giving herself a few quick little fondles to let me know she was excited. Then she motioned for me to draw near.

I thought she wanted me to crawl on top of her and give her a kiss, but when I moved between her legs she grabbed my shoulders and pushed me face down between her legs.

There was no doubt what she wanted -- though I was surprised at the duration. I figured a few licks to get things started, but her hands stayed on the back of my head and stayed there.

I knew my job and she was a paying customer. After a while I realized that she was probably getting off on being the dominant in the situation and did my best to show her I was there to please. I spread her legs wide and went in deep, and explored her as I really wasn't that familiar with the terrain. I explored a lot and reflected that if she was a man I'd be gargling by now.

When I felt like she was good and ready I slid down and invaded her tiny hole with my tongue just to see if I could get a rise out of her. She liked that and her grasp of my hair tightened, with some subtle moves of her wrist to let me know she expected me to do a good job.

Finally I think she came -- it was hard to tell other than a bit steadier trickle of moisture that ran down the canyon between the caves -- but she loosened the grasp on my head to the point I could move my eyes up to look at her. From her perspective I must have looked like I had a goatee.

She looked down at my and laughed. "Twyla you have no idea how many times I've dreamed about this view. Do you know how much I wanted you?"

I hadn't, and even with the secret out, I have to admit that I didn't have that ah-ha moment where I realized I should have seen the signs. It must have shown on my face.

"No of course you didn't." She sighed.

I sensed something hard in that statement, but also that I still had work to do. She had paid for an hour and I still had a half to deliver. Not sensing she was ready for anything else, I went back to work and the taste test confirmed that she had indeed came during my ass worship.

(That was not a service that I offered many men back in those days BTW. Only a few very high rollers who liked it enough to pay a premium and only if they were well showered and respectful.)

I had a good sense of time and didn't need to watch the clock, so I knew when another 10 minutes had passed and had felt and smelt that she'd enjoyed herself twice more. Post deluge #3, she stopped pulling my hair and stared petting it as if it were an extension of her body and I was part of her masturbation.

Soon she came to her senses, collected herself while I regained my breath, and quietly asked about taking a shower before the hour was done.

I frequently asked a man to use my shower before we started festivities, and some men asked for services that were best done in the shower for reasons of clean-up. Few asked for a shower post pleasure, which always surprised me as I knew women could probably smell me on their men when they arrived home without a chunk of their paycheck.

With Stacy for some reason I not only said of course, but asked if she would like company.

She laughed and declined, then seemed to rethink the idea and said maybe for a few minutes.

My shower was very good. (Again, I lived above a laundromat. It was superior hot water availability.) I led her into the spray, and she took the opportunity to allow herself to lick my body in ways that I quickly became convinced were new to her. She was unsure of herself and tentative, and ultimately, I believe maybe even just a bit grossed out.

She could not resist good oral sex -- and I prided myself on giving superior head -- but the reality of returning the favor ultimately didn't match the reality, I guess. She got on her knees briefly and then flew out of the shower soon after. (Maybe she realized just how well traveled that tunnel was.)

She pulled a towel from the rack and was dried and partially dressed by the time I finished washing (Something I did thoroughly as I had plans to go back to work).

Stacy finished dressing and watched me as I put on fresh lingerie and clothing for the evening. She said little and I wasn't sure of her thoughts.

I examined my own thoughts and realized I had little to reaction to it all. She was a Jane not a John and so maybe it should have felt different, but ultimately I was just hoping for a tip and eager for her to get the fuck out of there.

I sensed she felt my impatience and her pace quickened as she gathered her purse and slipped on her coat. (Her dress was still undone at the back. She had not asked me to help.)

She opened her purse at the door and pulled out a bill that was half again what she'd paid me. She tossed it with a bit of disgust on the entry hall table.

Looking up she caught my eye.

She hissed "you know, I married Johnny Munson. If you ever got back home, you stay the fuck away from him and you stay the fuck away from me too, got it?" There was an anger there that was real and deep and I responded.

She watched my face and when I had registered the expected amount of shock and dismay, she pulled open the door and exited triumphantly, her heels clicking on the hallway floor and stairway as she made her descent into the frozen streets.

I sat for a long time trying to figure it out before finally returning to the bar, resolving to no longer service women no matter what the payday.

At the time, I felt like she had attempted to insult me. Even though she'd paid me much more than my standard rate, it felt like there was an attempt to do harm.

Now through the fullness of time, I understand that she was just confused and had unresolved feeling for me and perhaps some sort of jealousy about a relationship I had with Johnny Munson.

But I still don't get it completely, because after years of thinking about it, I still don't remember who Johnny Munson even is.

If she hadn't dropped that last big tip, I would have assuredly told her so.