Author: o_l_d_t_i_m_e_r_

[M] 50’s and stripper sidepiece [F] 30’s

I had an 8 yr affair with a stripper, Rainy. Both of us married. She danced in a local nude club. Rainy was a petite, blonde, former gymnast, beautiful blue eyes, a Midwestern twang, with 2 kids. She was a former gymnast and cheerleader, still very flexible.
Her hubby (who she met at the club) made decent money, but Rainy liked her extra cash….and the attention. She had a daddy fetish. Her hubby was older than me. [She told me that her own dad abused her. She craves attention from older men. Strippers always have some baggage. Other than this, Rainy was as normal as a stripper could be]

I am a self employed professional, married, a bunch of grown kids, and a flexible schedule. About 6′ 2″, 200.
We fooled around mostly during the day when our spouses were at work. Sometimes my house, sometimes hers, sometimes in a motel.

This particular day we arranged for me to come to her house after her kids went off to school. I pulled inyo her driveway, and she shyly opened the front door. I was wearing a business suit, my normal attire. She only had a skimpy silky robe on, naked underneath, freshly shaved pussy, , as I instructed. Read more »

[M]y mil[F] stripper sidepiece acts the little slut that she is at a country club kids bday party

This happened 10 years ago. My stripper sidepiece was a married, blonde, petite blonde in her 30s with kids. Lets call her Rainy, not her stripper name but close. I was in my 50s, married, grown kids, a professional. We hit it off in the local nude club where she was the queen of the club. We both lived local, and took it outside the club for a wild 8 yr affair.

I texted her on a lazy spring Saturday afternoon, just to chat. She tells me she has her two kids at a bday party at a local semi-private country club. She didn’t fit in too well with the other moms there. She figured (prob correctly) that they had heard rumors that she was a dancer. The club was only 20 minutes from her house, so she had to get recognized at times. Anyway, she was bored watching the party and made her way to the bar.

Told her I’d be there in 15 at the bar. We could pretend we didn’t know each other, in case some of the other mommies (or her kids) saw us. Snuck a blazer into the car, made up an excuse, and sped off. Read more »

Threesome with stripper sidepiece and her stripper friend[MFF]

Threesome with stripper sidepiece and her stripper friend (MFF)

Me, 50’s married, grown kids, greying professional. Rainy, 30s, petite, blonde, blue eyes, married, kids, and a former cheerleader, now a longtime stripper. She danced at a local nude club. We hit it off and took it outside the club for an eight yr affair.

I’m at work one day and she texts to see if I can come over to her house during the day to fool around while hubby at work and kids at school. Oh, and one of her out-of-town stripper friends from the club is staying at her house. Rainy wanted a threesome. The out-of-towner wanted a “donation”.

Sure, why not. Never had a threesome before, now my dream comes true with 2 strippers. I was so excited I could hardly think. Mumbled something to my secy and bolted out of the office. Sped to the nearest ATM to get cash, figuring 3 bills to be about right. Quick stop at Walgreens for some condoms. I trust my sidepiece and she trusts me, and she’s on bc but for her friend, I’m gonna be careful. Read more »

[M]y freaky stripper g[f] and the gearshift

[M]y freaky stripper g[F] and the gearshift

I [50s married, professional] had a longtime affair with a married,MILf, 30s stripper. Call her Rainy. Blonde, petite, prettiest blue eyes. Hit it off during lapdances and took it further OTC. She had daddy issues, and got off being slitty with older guys.
One night I visited her in the club. She was normally very horny in the club, but this night she was wild. We danced in one of the booths. She told me she needed to get off. She slipped some lube out of her stripper purse, and put a few drops on my index finger. She sat sideways on the little bench, pulling my right hand under her ass, guiding my finger into her pussy. Rainy rocked back and forth on my finger. As she got more excited, she started sucking on her right tit. A former gymnast and still very flexible.
There were cameras in the club, but she got away with stuff because she would routinely give the manager a BJ. I think he got off in the back watching the cameras, seeing g her be so slutty.
She needed relief that night, and I focused on her needs, not mine, that night .
She threw her head back as I finger fucked her. The lapdance ended, but she wanted to come. She ignored the buzzer from the manager letting her know we had to get outta the booth, times up. Finally, her body tensed and her orgasm rippled through her. She gave me a small thank you kiss.
I told her she owed me one. Read more »

[M]y stripper g[F] willingly locked herself in my basement

Her, 30s, blonde, MILF, married stripper with kids
Me, 50s, married, grown kids, professional.

Met in a local stripclub and took it further, both bored, both wanted to take some risks. First in hotels, then our houses during the day, over an 8 yr affair. This particular day, she texted early in the morning, saying she was horny. I could not play in the morning, so I told her that I had to go to the office but text me when she was at my house.

I quickly came up with a scene I knew she would like since she is so submissive. I set up a scene for my basement, leaving sticky posts in my house to tell what to do, and went to the office.

A few hours later she texted that she was on my driveway. I had a house at the end of a cul de sac, so fairly private. Told her to go in the back door, it’s open, I’ll be there in 15, just follow my instructions on the post its. Read more »

[M]y stripper g[f] and the cucumber 🥒

A few years ago, I had an 8 yr affair with a married stripper. Call her Rainy. She danced at a local nude club, no alcohol. Rainy was mid 30’s, had 2 kids, and was still dancing cause, one, she liked the easy money, and two, she got off on it.
Me, in my 50s, married grown kids, doing ok in my own professional business.

In the club, the most we could do was FIV and an HJ. We hit it off, so we took it otc. We got really comfortable together, probably taking a few too many risks. We started in motels, but soon started using our houses while spouses were at work.

She came over one morning, scurrying inside. We didn’t have much time since I had an important business meeing at 11. She was dressed like the MILF she was. Jeans, sneakers, nothing sexy. After all, she was fitting our fun time into her suburban day while kids were at school. I had showered and dressed in my business suit. She had a daddy complex and enjoyed the power a dark suit gave me over her. Read more »

[M]y stripper side piece [F] for 8 years

Background…. fond memories of 8 yrs fooling around with a married stripper . Ended years ago when she remarried.

Let’s call her Rainy, a play on her stipper name.. Me, married in my 50’s, grown kids. She was in her late 30’s, blonde, petite, married, kids, and both of us were bored.
The club was local. We met there, and after a few years of lapdances we decided to take it further. We fucked a couple times a month at her house, or mine, or at my office, on cars, hotels, parks, wherever we could.

She would do almost anything I asked. Former gymnast and cheerleader, still very flexible. Liked being submissive. It was so liberating, a huge boost to a graying boomer.

So many memories.

One of my faves…….. she texted me in my office one morning on a cold winter day, and said she would come over for lunch. Told her to text when she was in my parking lot. My phone dinged a little after 12. “Great. My cars open. Go wait there”. Then I told her to find my winter coat in the back . “OK, got it, but why?”. I told her to figure out a way to get naked, and get in my coat. The obedient shut that she was, of course she did. She had no idea what I had planned, but she obeyed. She texted that she did it. I demanded she open my coat and send a pic. Of course she did. Read more »

Sunny [F] slips off her pretty panties for [M]e

Background—- Sunny was in her 30’s. Blonde, blue eyes, petite, maybe 5’1″. C cups, implants. Dancing in a nude club. Married with kids. Me in my 50’s, grey hair,6’1″, decent shape, married, grown kids, a professional. We met in a strip club and had a 7 yr affair.

Sunny and I liked to text each other just to brighten the day. Since we were both married, it was difficult to find time to get together outside her dancing schedule at her club. Most of the time that we got together it was the result of an impromptu text., like the one I am about to describe.

I’m sitting in my office on a summer day. Sunny texts me that she is bringing her kids to a birthday party at a local country club at 3. She texts me a pic of her in a breezy, yellow sundress, almost see through. Little straps on her shoulders, and ending way above her knees. A little too provocative for a mom at a birthday party, but Sunny likes to show off. All in all, a nice afternoon treat. Read more »

Surprise visit from Sunny [F] 30’s to [M] 50’s office

Sunny—- a stripper in her 30’s, blond, blue eyes, whitest teeth, cheerleader type. Petite. 5’1″ Was flat chested before she got C implants for her career. Married with kids. Went to college, smart, funny, but just fell into stripping for the easy money. As normal as a stripper can be. Submissive.

Me— professional, in my 50’s, grey hair, 6 ft plus, pretty fit, married, grown kids.

Both– bored and looking for some excitement. Had a 7 yr affair that ended after she got divorced, and remarried.

So….. one day she texts me and says she is out shopping near my office. I quickly come up with a plan. I tell her “great, come over. Text when you’re here. ” She texts from the parking lot of the office complex where I work in about 15 minutes. I tell her “I’ve unlocked my car, park next to it, and get in my car.” She complies. I text, “See my long overcoat in the back seat? Get naked and put on my coat.” She is an obedient playmate and of course she does what I tell her to do. Looking outside the window, I see her in my front seat in my long black coat. I tell the office that I am running home for lunch. Read more »