First Time With A Submissive Woman



What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? North Carolina
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Nonreligious
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? over 10
How many hookup stories have you here posted before? I believe this is my third

First Time With A Submissive Woman

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She and I had messaged each other on OkCupid for a few days and decided to meet up. We had sexted a few times and she had told me she enjoyed being told what to do. She also said she can deep throat, and I confessed that no girl had ever been able to do that to me, although several had tried. “I can,” she replied confidently. The first chance we were able to line up a night without our kids, I invited her over to my house. We met at a parking lot and she followed me out to my house, which is way out of town.

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 she got out of her car she remarked on how far out we were and said: “I’m not going to end up in your crawl space, am I?”
We laughed about it and I led her inside. It didn’t take long for us to get to it, we both knew why she came over. We went to my room and kissed and undressed each other. As soon as we were naked she dropped to her knees and took me in her mouth. Her oral skills were off the charts; probably the best blowjobs I’ve ever had, even to this day, have been from her. She was able to take about half my length in her mouth with no teeth, which many girls can’t do (or don’t bother to try) because I’m kind of thick. “Take it all,” I suggested, and she immediately tried. But only about half my length would fit in before I hit her throat.
“Uh,” she grunted and tried again.
“I thought you could do this,” I smirked.
She looked up at me. “Don’t worry. I can.” But hard as she tried, she could not get me into my throat. “Goddammit,” she sighed. “You’re bigger than I thought.”
“Hahaha. Overconfidence strikes again.”
“I’m sorry. I thought I could.”
“Get up.” I pulled her to her feet and told her to lay down. I kissed her in several places before directing my attention to her clitoris. “wow, you’re already wet.”
“Giving head turns me on.”
I love going down, and licked her inside and out, slipping a finger in and pulling back to find her g spot as I licked her clitoris. She was enjoying it but stopped me after a couple of minutes. “Too much,” she gasped.
“You don’t like that?” I asked.
“Right on my clit…it’s just too much stimulation. I’d rather you just fuck me.”
“Ask me nicely,” I ordered.
She looked at me with her big blue doe eyes. “Please fuck me.”
I laughed. “You’re learning.” She was the first of many submissive women I’ve been with, and I learned quickly how much I like being in control. I slid up her body and into her easily. She gasped.
“Look at me,” I commanded and she opened her eyes and looked at me. Our faces were almost touching, she’s tall for a girl. We stared into each other’s eyes as I plunged into her over and over. Every time she closed her eyes I would grab her arms tighter, ram my entire length into her violently, and order “Look at me!” She immediately would snap her eyes open obediently. I would go easy for a few strokes, then slam my entire length into her, hard, causing her to close her eyes again. It was a vicious circle.
“Does that hurt?” I asked.
“A little,” she answered timidly.
“Want me to stop?”
“No,” she answered again.
“Get on your all fours,” I directed. Immediately she complied. I got behind her again and slid in slowly. She moaned as I grabbed her butt with my hands and fucked her from behind. I love doing that. I started slamming into her harder and harder, my penis hitting her cervix every time.
“Oh God,” she moaned, “you fill me up just right.”
“You like that?” I asked.
“I love it,” she cried enthusiastically. We stayed in that position for a while until I got tired when I said: “Get on top of me.”
“Okay,” she complied. I rolled over and she straddled me. I guided my penis into her and she rode me, deeply, my cock head hitting her cervix again, over and over. “Jesus Christ,” she muttered at one point. “Good thing I like pain.”
She rode me for a while until I could tell she was getting tired. We had been doing it for at least a half hour by then. “Hey,” I said. “Why don’t you suck my dick some more.”
“Okay.” She got off me and knelt between my legs on the bed and started going down on me, looking into my eyes the whole time.
“You know I haven’t been able to come from a blowjob since my vasectomy.”
She took my cock out of her mouth and looked at me curiously. “I wonder why that is?”
I sighed. “I don’t know. I wish I could though, I love blowjobs. You think you can make me come?”
“I can try.”
“Well, you better.”
She took my dick out again, said “Yes, sir,” and immediately got back to work
I laughed. “’Sir,’ I like that.”
She giggled a little and kept going. She was really good. I hadn’t had my dick sucked like that in years. She wrapped both her hands around my shaft and sucked the head like a pro, stroking me up and down at the same time. “I’m just going to come in your mouth.”
She shrugged. “That’s fine.” It still probably took another five minutes of her expertly servicing me to make me come, but when I did I raised my back up off the bed and shoved deep into her mouth, shaking from my orgasm. She kept sucking, staring into my eyes the whole time, until the sensation got to be too much and I had to pull it out of her mouth.
I lay there panting. “Goddamn.”
She swallowed, then laughed. “Wow! That was a lot!”
“You like that?”
She nodded, then held her hands up. “Look, I didn’t even get any on my hands.” She laughed again.
“You are definitely an expert. Goddamn. That had to be one of the best blowjobs I’ve ever had.”
“Good. I’m glad you liked it.” She lay down beside me. Soon we fell asleep.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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? The next morning after breakfast we were sitting on the couch. She was already dressed and packed up. “Well, I guess I better go, I got to get my kids. You want another blowjob before I leave?”
“Sure, if you think you can make me come again.”
She laughed. “I did once, I probably can again.” She pushed my boxer shorts to the side and pulled my dick out. “Wow,” she remarked, “already hard!” She curled up between my legs and went to work again.
It didn’t take nearly as long this time. Maybe because I get off easier in the mornings, who knows. Anyway, a couple of minutes later I came in her mouth again. She looked up at me and smiled. “Two for two! Not bad, huh?”
I patted her cheek. “Not bad at all.”
She got up. “Okay, I gotta go! I had a really good time.”
“Me too. Let’s definitely do this again sometime.”

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? So many good things. The first orgasm from a blowjob in almost 3 years, she and I had a great sexual relationship that’s lasted off and on until today (we’re currently off because she’s seeing someone, last summer we were off because I was in a relationship), but we always hook up again. Also, she’s submissive and likes pain so I can fuck her as hard as I want.

What was the WORST thing about this hookup? I didn’t use condoms in those days very often, and a few months later she called me and said she was diagnosed with chlamydia. I’m not sure if she gave it to me, or if I got it from a partner in between, but I tested positive too. Took the antibiotic and learned a valuable lesson about condom use. Today I use them with everyone, and I get tested every few months.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I tend to take a more dominant role, which works well for me.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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? I think sex is a basic part of human biology, and people should be a lot more open about it with no hangups. Whatever two consenting adults want to do with their bodies is between them.

What do you think about the Casual Sex Project? I like it a lot

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