My name is Larry and I am a middle aged manager at a Fortune 100 corporation. I make good money but I am also a lifelong bachelor. The reasons for being a bachelor include autism, tragedy in my love life and a military career that only worsened the afore mentioned situation.
The first time I saw Jill, it was from a distance of about fifty feet. It was evening, I had just started with the company and I was busy being trained by one of the security supervisors (I manage safety, security, and maintenance divisions in a high rise complex). The supervisor noticed me noticing Jill.
"She works in the building" he said before continuing on with a number of things he needed to tell me that evening.
Over the next six months I was only able to talk to Jill a couple of minutes at a time as I made rounds with supervisors. Jill worked security, but even in uniform (which kills sex appeal for a lot of women) she stood out. Bright white skin, flowing red hair, a doll like face and a figure I estimated at 36-22-36. She smiled easily and was charming every time I approached her desk. The supervisors told me that she was a college student.
I came in on a Saturday morning to play "Manager on duty" and this is the first time I got a chance to talk to Jill for more than a few minutes. I learned she was a communications major in college and had just changed shifts so that she could spend more time in "lab" (working in a mock TV studio) on the weekdays. She was originally from Los Angeles and had moved to the south with her family when her mother's company transferred her. After a couple of hours she loosened up around me (I had spent serious time on the west coast while I was in the military and we talked about the west coast) and she asked me to keep a secret. She had worked as a stripper for a couple of years before coming to work for the company. The two reasons she quit was she had a (now gone) boyfriend and wanted to "be right" but also because she had cousins that came into the club a couple of times and had seen her naked.
I didn't disclose to her then that I frequented the clubs myself, but I later did. I also had brief affairs with strippers who would meet me at hotels for sex. Jill told me she had done that also, but only with two clients. One was a rapper who dropped a lot of money on her, but only had two dates with her. The other was a guy who became her boyfriend for about six months (he was the boyfriend when she came to work for the company).
Jill became a confidant and I ended up giving her my cell number (a violation of company rules). Once a month, when she got off duty we would meet for dinner. During these dinners Jill would be friendly, but also I noticed she kept a professional distance. We discussed the clubs, her family, my family, work and the west coast. Once, we got into a discussion about the clubs that bordered on the sensual. She talked about how she gave lap dances and how managers would check her out. I asked if any of the managers asked for "private performances" or anything like that.
"Oh, hell no", she answered, "or I would end up owning the club outright."
That killed the idea of me asking her for a lap dance.
Finally, it was time for Jill to graduate from college and she put in a vacation request for two weeks. I immediately signed it, which earned me a smouldering hug and a kiss on the lips (she had never done that before).
It was a month before I saw her again. I came in on Saturday morning to be manager on duty. She called me on my cell to ask if I would be by her building that morning. I told her I would be busy until about ten, but we could talk then.
At ten I came in her building and she greeted me with a hug. I was glad it was the weekend and that no one saw that (or the prior kiss) or I could be in BIG trouble. We did catch up for half an hour and she talked about graduating, seeing her extended family for the first time in years and truly enjoying the celebration-which seemed to last a couple of weeks. But she also told me that she had seen friends from the strip club and they got her back into the club for one night. They got her up on stage, made it rain and gave her lots of booze. After telling me that she reached in her purse and pulled out a paper and handed it to me-it was her two week notice.
"I miss the club, I'm going back, " she told me.
I was bummed about losing a friend, but at the same time I now had the opportunity to see her naked-and maybe more.
About a week after she left I went to the club she said she worked at. I didn't see her there and I spent about four hours there. On the way home I tried her cell number-voicemail. I tried again a couple of times over the next two weeks, but no success. On her cell it got to the point where her voicemail was full and then the number was disconnected. I tried other clubs somewhat near her club, but to no avail. After six months, I gave up.
Three years later I walked into a very fancy club on the north side of town. I usually avoid it because there are a couple of other clubs where it is easy to get laid with decent looking chicks, but these clubs were suddenly a lot stricter. The upscale place has extremely beautiful strippers but it is hard to get anything other but a low contact lap dance. I did get laid a couple of times there a bunch of years before but they had seriously tightened up since then. So, as I walked onto the main floor the last person I expected to see was Jill (she had told me she was strictly a "west side girl") but there she was.
Jill was at the base of the staircase talking to another stripper. She was as striking as she had been before. I discretely and quietly walked up to them. She did a double take, then seeing me she smiled broadly, threw herself into my arms and laid a very friendly kiss on my lips. "Come on" she said, taking me by the hand and leading me to a table in the quietest corner of the club.
We spent half an hour catching up. She explained the snafu on her phone as saying the phone was stolen and she changed out phone numbers by going to a different company. She had also been quite a vagabond as she had worked at a number of clubs, which explained why I couldn't find her. After half an hour I asked the question that floored her:
"Jill, can we go in the back?"
She was visibly stunned and I actually saw her "GULP". I guess she figured I would always be "friend zoned" and not the guy who would see her naked, but there it was-I had asked.
"Okay" she said in a resigned manner and we found a room I liked under the stairs. It was more quiet than the table we sat at and I had once laid a Katie Holmes lookalike in the room. She came in in the room, seated me, placed her clutch on the table, took off her top and stripper platforms (her feet hurt) and she started a very sensual lap dance.
First, she rubbed her front against mine, slowly sliding to her knees onto the floor, taking time to caress my now stiff member. She stood, turned and eased into my lap. Leaning back, She placed my hands on her C cup tits. Using her fingers, she manipulated my fingers so that her nipples were massaged. She leaned her head onto my shoulder and gently hissed. After a moment, she stood, turned towards me, staddled my lap, then placed her breasts in my my face. First one, then the other, she placed a nipple on my lips. She ground her pubic area into mine, taking time to lean forward and would softly moan in my ear while her fingers gently caressed the base of my skull.
So, that was her lapdance, only there were slight variations, such as breathing her hot breath onto the crown of my dick through my pants. On the third song, while her back was on my chest I moved a hand from one of her tits to slip inside her G string. She immediately pulled it out.
And so the lapdance went on. Finally, during the fifth song I made a different move. She was standing in front of me. I had one of her nipples in my mouth. I placed a few fingers on her clit, but massaged it through the fabric of her G string. She stood stock still while I continued to do that. After a couple of minutes she let out a loud moan. She placed a hand on top of my head and locked my head in place as I continued to work her nipple with my tongue. Her breathing deepened and sped up. She let out another loud moan. She was beginning to tremble. She let out a shriek, pulled away from me and ran to the doorway, gripping it hard as her body shook. I ran up and from behind pushed my groin into her behind, reached around and played with her clit some more. Her body convulsed some more. She quickly spun and violently pushed me into the chair, straddled my lap and placed her crotch in my face. She pulled the fabric of her G string aside and pushed her clit into my mouth. I licked and sucked at her clit. For her part she ground her pussy into my mouth while she noisily panted and slapped her open palms against the corner of the room. Then, quite suddenly, she jumped down, extended an arm and kept me at arm's length for several minutes as the body quakes and rapid breathing subsided. About the time she recovered a stripper and customer appeared in the doorway.
"You two alright?" she asked. "We heard the banging and we were worried."
"Everything's fine" Jill told them.
We returned to our chairs.
As Jill dressed she looked at me suspiciously.
"You, okay-really?" I asked.
"I'm fine."
She stood and extended a hand, palm up as in "pay me."
I counted out fifteen twenties. Fully dressed, her clutch in one hand, money in the other, she spun and quickly left the room.
I returned to the club three nights later. At first I had difficulty finding her, but then I happened to see her exit the VIP room with an extra large rapper (he was 450 pounds if he was an ounce). She quickly headed into the dressing room and I had to wait a while for her to come out. When she finally exited, I lingered nearby. I caught her attention and she immediately knew what I wanted.
When we went to the back room, she did her usual lap dance (in slow motion), but she also watched the door and asked to let her know if I saw a manager before her. I kind of thought what she had in mind and when a manager did walk by and poke his head in the room, Jill discretely knew what to do. She sauntered up to the doorway, watched a minute, then climbed up to straddle my lap while she pushed her pussy into my mouth.
"You know what to do, " she said with a smile.
For the next fifteen minutes I ate her out as she built up to orgasm. When I felt her legs tremble I knew she was in final sequence before blast off. I knew she had two orgasms, then she climbed down and started her slow motion lap dance again.
"Watch the door, " she said again.
When a manager walked by again, she let me eat her out again, only this time when she climbed down she called it a night.
"I have to go home, " she said as she dressed. She collected her money without another word and left.
Four days later, I returned to the club. It was easier finding Jill this time but it was hard finding a room because it was Saturday night and the club was packed. She was also being a lot more cautious this time and kept me away from between her legs. She was doing her lap dance, being sensual and kind of was in her own zone. I was actually getting bored and she was very startled when I asked: "Jill, when are we going to make love?"
She froze. "What?" she asked, clearly blindsided.
"You've been to a hotel before with customers and we've known each other for five years. What do you say?"
She pondered the question for a few seconds, "okay" she agreed "but it has to be at least four hundred, and I do like to be tipped, " she concluded with a smile.
We swapped phone numbers, then she asked how much time did I want to spend with her in the hotel.
"I prefer an all nighter. Anything under two hours is just a quicky for me."
"I can't do all night", she said, but with a smile she added "I'll give you enough time to do your thing. By the way, where did you learn to do that thing you did to me? I mean, you just made my head explode."
"In the Philippines, from a mama san" I told her, then imitating an Asian accent I added "I teach you to please me, not you to please other girls-understand?"
"I have to take three days off from the club after spending time with you. For real. You ruin me for other men. I need money right now, so I'll call you and let you know when. Don't come back to the club until I call you."
I obeyed her request but four days later, at work, I was stunned with a revelation.
There are a cadre of off duty police officers that work in the high rise complex. Technically I am their boss as I overlook the budget from which they are paid-but one of the cops is the one that makes schedules and assignments.
I had not seen Charlie in several years. The PD had him working another assignment and he came back after Ron (the head cop) ran off one of the cops for sleeping on duty. Charlie and I started catching up, enjoying each other's company. About twenty minutes into the conversation I asked if he remembered Jill.
"You mean stripper Jill?" he asked.
"Everybody knew?" I asked, caught a little off guard.
"Only a few of the cops", he answered, "my partner's godfather works vice and tried to proposition her one night. She was too smart, wouldn't take the bait. He ran her background and he found out she used to work here. Did you know about the trouble she got into earlier this year?"
"No, " I answered.
"Her and her boyfriend got about eight gallons of prescription strength cough syrup from an accomplice in a warehouse. They didn't know the warehouse was being watched. They got popped about a mile away."
"Why take that stuff?" I asked.
"They mix it with strawberry soda. It's a party drink."
"Holy crap" was all I could say. Even though I liked Charlie I wasn't about to spill the beans about my upcoming date with her.
Saturday afternoon Jill called me. She must have been in the dressing room of the club, I could hear the bass in the background. She told me about a hotel that charged by the hour that wasn't anywhere near the club (she didn't want to be seen at the hotel a half block from the club). She told me she would see me about nine and for me to text her the room number.
About nine thirty she knocked on the hotel room door (she had texted me she would be late). She was wearing flip flops and sweats. She was also carrying her stripper bag-which was quite large. I let her in and we quickly kissed before she set down her bag. I then showed her the surprises I had for her.
I didn't want to be just a "John" so I got her flowers in a vase. I also had a stuffed doll and her favorite drink (a wine cooler) cooling in an ice bucket. She thanked me for the gifts, then downed one of the wine coolers in a matter of seconds. She smiled and started to unzip her sweat top.
"I've been working at the club all day. My motor is running. Let's get this party started" she said with a smile.
She was naked in a matter of seconds, then helped me undress. We fell onto the bed, passionately kissing. Jill only allowed about thirty seconds of that before she directed my head to her chest. As I had done at the club I started working a nipple with my tongue while a hand went between her legs and started playing with her clit. I looked up and her eyes were closed as she was entering bliss. By the time I finally went down on her she was very primed. In mere minutes she had her first orgasm, during which she grabbed me on top of her head and whispered "Wait" while she went through the throes of orgasm. Whem her body quakes subsided, she allowed me to proceed.
I ate her out some more, then positioned myself over her. After I entered her and began to work my hips we were face to face and she had the biggest smile on her face. I moved in and we began kissing. My motions into her were sometimes slow and sometimes fast. Her face took on a look of concentration and she continually slid her hands up and down my arms, sometimes pausing on my shoulders. I was in a fast motion when she suddenly begged: "Don't stop, please don't stop."
I continued to work my hips. Suddenly, her orgasm hit. She locked my face to hers and locked her legs around my body. I felt her spasm under me. It took several minutes for her her spasms to subside and she eventually unlocked her ankles behind my back. I resumed fucking her. Several minutes later I was on build up to detonation. My orgasm came and I had three major spurts and three minors. Spent, I collapsed next to her. She curled up next to me, placing her head on my shoulder while draping a leg over. I started to say something, but she placed her hand on my mouth and said: "Shhhh..."
We laid like that, in silence, for half an hour while she employed her hand to play with my chest hair. Then she got up and headed for the bathroom.
"What are you going to do with the rest of your night?" she asked as she stepped into the tub and used the shower wand to rinse off.
"I don't often stay in hotels. Maybe I'll just stay the night and watch TV. What about you? Why don't you stay the night?"
"I can't. I have an aunt who is opening a club. My cousins will be there."
"What kind of club?"
"It's an after hours club."
She caught me in mid thought.
"No", she told me. "You're not going. I'm not going to introduce you to my family."
*****************************************************************************
The following Friday night I sent her a text: "Booty Call?"
Her reply was: "Can't tonight. Will tomorrow. Wait for my text."
I didn't know it then but she was cooking up something for me.
At 11:30 the next night I got a text telling me to meet her at the Century club, which was not her club.
The Century club is a northside club not all that far from the upscale club where she works. As I pulled into the parking lot I noticed it was quite full. I had been to the club a couple of years before on it's opening night. From news reports that I had seen, the club vacillated back and forth from topless to nude because of an alcohol licensing issue. When I got to the front door there was a sign reading that the club was closed for a private party. Jill had sent me an invitation so I opened the door.
As I stepped into the lobby a man raced towards me. Jill, who had stood next to him stopped him with "I know him, let him in."
The man froze in his tracks, then stepped aside. Jill stepped up, smiling, taking me by the arm. I was about to ask her what that was about but we passed a satellite stage where a completely nude girl gyrated. Her chest was almost completely flat. She had her hair tied back in pigtails and she was shaved down below to make her look younger. Three men with bills in their hands drooled as they watched the girl.
The Century club has a unique design. There is a semi circular ring of booths against the walls. There is a main floor with tables and chairs. On the main floor there is a main stage but also a satellite stage. On the satellite stage a nude and seated stripper smiled as she was being fingered. Jill led us into a booth and pulled a curtain to close off the booth as we sat.
"What is going on tonight?" I asked completely astounded.
"The club is having a private party, " came her vague answer as she untied her string bikini top.
"Do you usually come to this club?" I asked, uncertain of what was going on. She knew I needed some clarification, but she was still kind of vague.
"My cousin has an i.d. issue, so, she can only work certain clubs, or when a club has a private party, like this", she replied as she straddled my lap.
"Was your cousin that girl we passed on the small stage?"
"She might have been" she answered just before she silenced me by popping a nipple into my mouth. We made love again with the unique feature that I ate her out as she lay on the table in the booth. We then fucked on the bench in the booth. After we did the afterglow thing we both needed to pee. As we drew back the curtain I saw some guy actually openly fucking a stripper at a table in the center of the main floor, his pants were down and she was bent over a table. There was some other fucking going on the floor with the guys fully dressed and the strippers at least trying to pretend to give lap dances. Jill's cousin was on the main stage. She was actually using a champagne bottle like a dildo.
At five minutes to two the club DJ warned that it was five minutes to closing and everyone needed to "finish up." As he said that I noticed some action going on in the DJ booth between him and Jill's cousin.
At two, the lights came on in the club. The club looked real different. A migration started towards the front door-customers and strippers. Some of the strippers were topless, a couple of them were fully nude. When the customers reached their cars the strippers affectionately said goodbye. Jill had only escorted me to the front door.
Jill stood me up the following Saturday. First, she told me she would meet me at the hotel, then told me she was unavailable. I was horny and needed relief. I don't know what came over me, but I went to the Century club. It had crossed my mind that I would find Jill's cousin and maybe fuck her-just for revenge, but she wasn't there. I did find a very attractive light skinned Mexican woman. When she came back to my booth she started giving me a lap dance. About thirty seconds in I asked if she fucked.
Sharply she said:"Two hundred, show me the money."
I opened my wallet and showed her my wad. She immediately went to the floor and pulled down my zipper. She went down on me for about thirty seconds, then mounted me. I didn't even have time to pull out a condom, let alone put one on. She fucked me for about ten minutes, then quit.
"You no cum?" she asked.
"No" I answered.
"I finish, pay me."
She held out her hand and I paid her. She immediately got up and left. I got up, zipped up and took a look around the club. I didn't see any other strippers that interested me so I left. I then drove over to a club that I know to be a skeevy place.
This club is fully nude and actually kind of small. I've only ever seen about five strippers working the place at any one time. I sat down and looked around. After about ten minutes I only saw about three strippers. One stripper was talking to a man and the other two were talking to each other. They saw me and chose to ignore me. I would have walked out just then but I paid a twenty dollar cover to come in. Finally, I did see another stripper come out of the dressing room.
She was thin and wore a tight cocktail dress. She had long hair and she wobbled a bit, I wondered if that was from booze or something else. She scanned the floor as she wobbled. She saw me and wandered on over. She smiled lazily, said "Hi" and extended a hand. I shook her hand and she sat down.
She was cute and tried to make small talk. From the slurring of her words she was definitely drunk or on something. I cut to the chase and asked if she wanted to go to the back. She smiled and said yes. She stood up and took me by the hand.
We entered a room with cheap plywood walls. The furniture was the cheapest. I've seen furniture like that in cheap places-like in an American Legion hall. She pushed me into a seat pushed up against a wall. She plunked her clutch down on a tiny table then wiggled out of her dress, which she also threw on the table.
She had small breasts with small, strange, droopy nipples. Between her legs she had at least three days growth, if not more. She immediately straddled my lap, grinding both her hips and chest against mine. I decided to cut to the chase: "Do you fuck?"
Her face lit up. "Yeah, you got a condom?"
I fished a condom out of a pocket while she unzipped me and fished out my dick. Then, for a moment I waited while she actually played with my dick. She noticed me noticing. "Oh sorry", she said with a smile, "I really like dicks like yours." I handed her the condom, which she slid on then she mounted me. She hooked a hand around my neck and went to work with her hips. The only problem with this is that our rhythms weren't matching. About the time she'd get me built up, she would change up. I decided to change things up by grabbing her ass, lifting her and switching it so that she was now in the seat.
I then began pounding her. From the look of bliss on her face she was enjoying this. I felt the build up to detonation and then I shot off into the condom. She must have felt it because she gasped. We both froze in the afterglow. After a minute she got kind of a goofy look on her face. "I guess we should have talked money" she said.
"Is a hundred fine?"
"I'll take it" she said.
She reached down after I pulled out.
"Did you nut in me?" she asked. "Did the rubber break?"
I slid it off and showed it to her. "Nope."
She got a goofy grin. "I guess I enjoyed myself. Do you want to do it again? We have a VIP room. We can have more fun."
I had already rolled the dice by having unprotected sex once tonight and even though I did use a condom it was even money that she probably had at least one STD, so I declined her offer. She then counter offered.
"My brother will be here at ten to pick me up. We're having a party. I'm pulling a train. Do you want to come?"
She finished the question with a giggle. HOLY CRAP!! She was going to get gangbanged and her brother might be one of the group? Or at least watch her get banged? Red flags went off in my head. I politely declined.
The following Thursday my phone rang, it was Jill.
"What are you doing?" she asked.
"Thinking about you", it was the truth, "I was wondering if you were free Saturday?"
"How about tonight?" she quickly countered.
"Tonight?" I was startled.
"Yeah, I already have a hotel room."
"Why do you have a hotel room?"
"I like to get away from my mom sometimes. She's on a holy roller kick. When can you be here?"
"Where are you?"
"Where do you think? Room two oh three. You know what I like to drink. Pick some up on the way. I'll put some ice in the bucket."
I looked at my watch and did some calculations in my head.
"I'll be there in an hour."
"Okay, see you then." She hung up.
I jumped in the shower for a quicky shower and deciding to not take chances threw together an overnight bag and clothes for the next day. I rushed out the door. As I neared a gas station near the hotel she texted me.
"I only paid the hotel manager for two hours. Pay the rest if you want an all nighter. He's expecting you."
What kind of game was she playing? She gets a hotel room to get away from her mom but only pays for two hours? Did she already have a customer tonight? I wasn't being jealous but I do draw the line at sloppy seconds. I decided not to worry about it, but still-I was a little wary.
When I arrived at the room she was dressed casually and seemed to be in rush to start anything, but after an hour we did start making love. I gave her several orgasms and I stopped at one. She took a shower and then we watched a movie together before falling asleep. Before I headed out in the morning she told me to call her when I got off of work to check her availability.
When I called her that afternoon she was out shopping with a friend. She did instruct me to get a hotel room again. I did just that, but when she arrived she hit me with something startling-she could only stay two hours because she was going to pull an all night shift at a black strip club. I felt cheated because I don't like to be rushed. As she showered she explained that she was doing the all nighter because her best friend was overweight and it was the only place she could dance-and she wanted to hang out with her friend.
The black club became a pattern for her as she was there every night that week. On Saturday she called me to ask if I would forward her 400 bucks as she had bills due and she was only taking home 35 bucks a night at the black club. We argued as it made no sense in that she was taking home 300 plus a shift at the club where I met her but she would decide to make much less for longer hours (the black clubs make the girls work 11 shifts instead of 8). We finally resolved she would earn the 400 meeting me Sunday afternoon at the hotel.
When we got done at the hotel on Sunday, as I paid her she said: "I don't see why you're being such an asshole about this. You could have just forwarded me the money."
I reminded her that I worked hard for the money and things grew heated. In the heat of the moment I let slip that I knew about the syrup thing. She accused me of spying on her. I tried assuring her that I found out by accident but she wouldn't accept that. A few minutes later we decided to mutually delete our numbers from our phones and that was it. It was over.
A friend at a strip club website advised me that I should have ended things after two dates, that familiarity breeds contempt. Perhaps he's right.