The Barber Was a Lady



What’s your gender? Man
How old are you? 64
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland, Ohio
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? happily retired
What’s your current relationship status? I have a submissive who I allow to serve me four or so days a week and a married mistress who is in a sexless but otherwise loving marriage,
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I am a dominant with spanking, corset, and leather fetishes
How many sexual partners have you had in your life (including oral sex)? I would guess between 60 and 80, perhaps. Perhaps slightly more. Less than 100, surely. I don’t know for sure, I don’t “keep score”.
How many hookup stories have you here posted before? 5

The Barber Was A Lady

How long ago did this hookup happen? About a year and a half ago

What was your relationship status at the time? I had my friend with benefits in her sexless marriage and was otherwise dating around. Nothing serious or paerticularly satisfying.

How would you best classify this hookup? It was the beginning of a relationship that is still evolving. It was casual at the time but I think it is less so for her now. Me, I’m still ambivalent and still open to other relationships.

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was 5’8″, a nice figure, good tits and fine ass, pretty, 44. She had a faux hawk, with the longish top dyed platinum blonde and the very short cut sides her normal jet black hair. She had a pierced eyebrow and a lower lip piercing. Oh, and GREAT legs! Mmmm. She was a barber in one of those high end barber shops where all the women are hot and dress hot and wear high high heels and they fuss over the customers and pull in big tips for it all. She was by far the oldest of the barbers, the others all in their early to mid thirties and even a couple in their twenties. A younger friend of mine who frequented the shop told me she was a little old for his tastes but that he could see she was hot and thought she’d be right up my alley. I was curious so I made an appointment with her. When I saw her I recognized she was pretty but her look was too young and modern for my tastes, I was more into professional women, and I doubted anything would come of it beyond enjoying her attentions while she cut my hair.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, it was strange. I decided I wasn’t interested and was kind of non-committal as she tried to draw me out in conversation. I felt too old for the whole barbershop, not just her. It was an interesting experience, just not my cup of tea. To avoid having to give monosyllabic answers to her cajoling questions I began to pepper her with questions about how she got started in barbering and how she got a job at this particular shop. She had quite a story. She’d gotten pregnant in high school, dropped out, had three children in 4 and a half years and then her husband abandoned them. She had no skills or education and three very young children. So she ended up selling cigarettes and dancing in a “men’s club” because she was pretty and had the hot figure that some women get on a starvation diet. Her mother, an alcoholic, lived with them and watched her children at night. And so on. Over time she got her GED, worked in sales, and eventually went to barber college. I listened and was appropriate and nice and when it was over I gave her a $30 tip on a $25 haircut. She looked at the money and finally she gave me the $30 back, saying she didn’t want it. I was shocked. “No?” “No, I want you to take me to dinner. You’re the last customer of the day and I wanted to finish talking to you. It doesn’t have to be a fancy place. Spend the $30 on dinner.” I was totally stunned but it has long been my policy that if the rare woman found the courage to ask me out, I would reward that courage by saying yes. So I did. We went to dinner, I dropped a hundred dollars+ on dinner, she had a couple of double vodkas, in fact, three, I think, in the course of dinner and seemed perfectly fine, which meant either she was very good at hiding how drunk she was or she was an alcoholic. She said she never expected me to take her to such a nice place, that it wasn’t necessary. To be honest, we went to that restaurant, which I frequented, because I wanted people to see me in the company of such an attractive younger woman. I wanted to get something out of the night, right? Well, the night wore on and it was time to go and I asked her if she could drive, she said she could, she seemed fine, actually, when we walked to our cars. At her car she put her arms around me and told me I could kiss her and that I was very nice, a real gentleman, and she’d like to go out with me again. I told her I wanted her to come home with me that night. Totally spur of the moment, spontaneous, unplanned and unexpected–and I mean by ME. “Oh, my god, look at you!” she said. I just looked back at her. “Really?” she said. I still didn’t say anything, staring into her eyes with kind of a half smile. She looked at me for a long minute, up and down. “OK,” she finally said. She got in her car and followed me to my condo. .

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When we got back to my condo she looked around and said, “Jeez, this is really a nice place”, which it is and was. She went out on the balcony which looked out over downtown and the lake. “Wow,” she said. “I think I need another double vodka.” “No, no more alcohol.” She said she was a little afraid. I told her don’t be, she could leave any time she felt uncomfortable. She said, no, she was afraid of herself. Why? She said this was the kind of place, I was the kind of guy, she’d maybe do anything and that was a little scary for her. It was music to my ears and, speaking of music, I went back inside and put on some jazz, Dave Brubeck, I think. I sat on the couch. She eventually came back in off the balcony and sat a little away from me on the couch. “You can still go if you want to, if you’re now thinking differently,” I said. She looked at her hands for a moment, then at me, then back at her hands. “No, thanks, I think I want to stay.” I went to the bookshelf and pulled out a book and handed it to her. It was Diane Klosterman’s photo illustrated “Story of O”. “Look at this,” I said. She leafed through it slowly. She looked at the photos, some of which were harsh, then at me, then back at the book. She let the book slide off her lap onto the floor. “Are you going to hurt me?” “You can leave any time. You can leave now.” She looked around the apartment, again slowly, trying to take it all in. If she wasn’t sober before, she certainly was now. “Are you going to hurt me?” “Possibly. It partly depends on how well you obey.” “But you’d like me to disobey, wouldn’t you?” I didn’t say anything. I just looked over at her silently. “You can leave, I won’t stop you, but if you stay…” There was another long pause. She looked at the book, now on the floor and then around the apartment again. Then she looked at me for the longest time. Finally, “No, I think I want to stay. I think I want to see where this goes.” “Are you afraid?” “A little.” Another pause. “Take off all of your clothes,” I said. “Stack them neatly on the chair over there. Keep your heels on. Then stand in front of me with your feet together and your arms at your sides.” It took a moment but she looked down, got up and slowly started taking off her clothes. She glanced over at me, not into my eyes but just to see if I was watching, and of course I was. Soon enough she was standing in front of me totally nude save for her heels, which were tight together, as she’d been told. And she was…lovely. Except she had a little pooch stomach with her clothes off and an ugly caesarean scar, maybe 6 or 8 inches long. Pretty ghastly, actually. But lovely perfect breasts, a thick fleece of pubic hair, and those great legs of hers. Everything else about her was great. “Turn around,” I said. “Slowly.” She did what she was told. A little cellulite gooseflesh but otherwise, so perfect. Now it was my turn to say wow, to myself of course. It was unexpected that her body would be so nice. When she was facing me again I asked her if she’d whored herself out at the men’s club. Her eyes got a little glossy but she held herself proud and said, “a little”. She’d needed the money for her and her kids. I asked her about the caesarean scar and she flushed red. She said she’d never had the money to get it fixed. She apologized for it, looking down. I got up, took her hand, and led her to the bedroom. She sat on the bed while I stripped. I got onto the bed with her and held her. I kissed her. “Are you going to spank me or something?” I smiled. “Not this time,” I said. “Or perhaps in the morning. But not now. Now I’m going to show you what a good girl gets, because you’ve been a very good girl tonight.” I spent a long time kissing her, fondling her, holding her, telling her she was beautiful, stroking her, and then fucking her. More than an hour, I’m sure. She was jelly when I was done and soon fell asleep. I was pretty damned pleased myself.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We slept together that night and in the morning I did give her a thorough spanking before fucking her again. And then I sent her home to get ready for work. I told her she needed to call me when she took her lunch and she did. I told her to get her clothes together at home and then bring them that night so she could spend a few days with me, that I wanted to train her to please me. And she did. And I did. It was really rather amazing, how good she could be, how obedient, how loving. The pain, the punishment, was not an issue between us. I started her on corset training. Her waist was about 27″ then. It’s 23.5″ now. And the corset covers her caesarean scar as well, which she very much likes. Cheaper than plastic surgery, I told her. She’s taken to this lifestyle amazingly well. She was born to be a submissive. She just had to learn who she was. She is still with me four nights, sometimes five nights a week. She wants to simply move in with me permanently. I feel funny about it all. I mean, she’s the perfect sex object/partner, she works hard to be that. She never complains. She’s quite happy and she still cuts hair. It’s OK for now but I’m on the brink of becoming an old man. And then what? Plus, she’s not educated, she has very different interests (Honey BooBoo???), there are a lot of differences between us. She’s been with me over a year and a half now and I’m still waiting for the wheels to fall off. We’re too different. But my god, when it’s good, it is GOOD!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) I have a vasectomy.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Power / Dominance, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? She gave her clear but very apprehensive consent.

To whom did you talk about the hookup? How did they react? I’ve talked to a few people about her and she’s met some of my friends. Hell, she’s at my apartment most of the time she’s not working, unless of course we’re out together somewhere. Still, she hasn’t met either of my children yet and I feel funny about that, as does she. I haven’t shared with anyone the S&M undercurrent going on in our relationship.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Almost everything. I mean, she cooks and cleans for me now, she’s a dream submissive, she loves our sex life, she’s very happy and that makes me feel good. And she is so lovely. Sometimes I look at her and can’t believe how lucky I am. That’s what the best thing is, she almost always makes me feel good, and all that came as a result of this hook up.

What was the WORST thing about this hookup? I get a little frustrated by her ignorance and low brow tastes, though of course I understand it. I don’t much care for 2 of her 3 children, the way they treat their mother. They are just low class. She loves them, though, so what am I supposed to do? Still, I don’t see her kids much at all. Also, I’m 18+ years older than her, which is a little problematic now and will probably become more so in the future, given that I’m only getting older. But the actual hook up itself? There was nothing bad about it at all.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I’m old now and set in my ways.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It’s funny how something you think is going to be a one-off, if even that, somehow morphs into something much more. I never expected it to happen, I surprised myself first taking her to dinner, then asking her back to my place, I gave her every opportunity to say no and leave. She told me she couldn’t believe herself that she kept saying yes, that she actually stayed that first night even though she said she was very apprehensive, as you would expect. But she was more curious about it all than apprehensive and she said I kept seeming so nice even for being so threatening. Believe me, this isn’t how it all usually goes in this lifestyle. I think she suspected she was a submissive and was curious but had never acted upon it. Maybe it was just meant to happen. Anyway, that’s what she always says.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Casual sex has played a disproportionately large role in my sex and social lives. I never would have guessed this when I was an altar boy. I guess I’d like to see people more open to it and accepting. Even now it seems a little shameful and I don’t much talk about it. People don’t understand, they can’t relate.

What do you think about the Casual Sex Project? I think it’s a start. I hope it helps.

You have a hookup story to share? Submit it here!