Jackson, 46, on Childhood and Older Women

This is Real Sex
Jul 11, 2018 · 19 min read
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Photo by Priscilla Du Preez on Unsplash

Start at the beginning with your first memory of yourself as a sexual being.

I remember exactly when it was. I was maybe 11, 12. In bed I was rubbing myself and that felt good. That was definitely the first erection that I recall. I’m sure that there were other times, but I just didn’t pay attention to it.

Why do you think you paid attention to it in that moment? What was different?

It just felt different, a little euphoric and different. It was a little scary and a little like, ‘What’s going on?’ I definitely grew up in a house where that wasn’t really discussed, so it was discovery by trial and error.

Why was it scary?

I had no idea what was going on with my body. I just had no clue about that, or the birds and the bees. I was never read a book. There was no guide.

Did you know there was such a thing as masturbation?

Not at that point. I soon found out that was what that was all about.

Clearly no concept of orgasm at that point?

Clearly no concept of orgasm, and shortly thereafter, the next night I couldn’t wait to get back in my room. I went to school that day, I remember, and I got home from school, and I was like, ‘Oh, I’m tired.’ I closed the door, went back in my room, and did it more. Nothing happened. I don’t think I orgasmed for a couple weeks. Then it was just like, ‘Wow, what was that?’ I grew up with an older brother. I actually asked him, ‘Dude, here’s what happened. Have you ever done that?’ He’s like, ‘Well, yeah.’ It felt more like I wasn’t a freak.

When you first started those first couple of days, you didn’t orgasm, but it felt really good?


Was there a particular feeling that it gave you that you wanted other than the euphoria?

Curiosity. I was very curious about that. Why was that happening to me, and just why? I had a lot of curiosity around it.

Did you know that it was considered a sexual act?


Was there any fantasy for you around it?

No, not at that point. I had no idea. I wasn’t into girls. There was no visual anything about it other than the act itself and it feeling good.

Do you remember the first time you came?


What was that like?

Super scary. It was like, “What is that, and why did that just happen?” The feeling was — over those first few weeks, I could feel something building up in a way, like, “Wow.” I don’t know.

When I look back, and obviously now I know, the emotions I was going through at that point were, ‘Is that it? That feels really good. Let’s try it again. Let’s do it again. Do it again.’ Then all of a sudden, ‘Whoa! That happened!’ It was a game changer for sure.

When you first came, what were you afraid had happened or would happen? Do you remember your fears?

Yeah, I didn’t know what semen was. I didn’t know. ‘What’s this? Did I just piss myself? What is this substance that just came out of my body?’ That was a little scary. Then I asked my brother, and then it was like, ‘Yeah, you’re not a freak.’

Was it hard to ask your brother?


Do you remember how that conversation went?

Yeah, I remember where we were. I remember I was in his room, and I just asked him. I said basically, ‘Dude, here’s what I did, and here’s what happened,’ and he looked at me like I was a retard. He was three years older than me. ‘Yeah, dipshit. There’s nothing wrong with that.’ We didn’t talk about it. I grew up in a very — you don’t talk about shit. We just didn’t talk about it.

. . .

Before you started masturbating at 11 or 12, do you remember having any sexual feeling, attraction, to — sounds like you are heterosexual?

Yeah, I am.

Any attraction to girls before then?

In first or second grade I think a girl kissed me in a tunnel at school. I was like, ‘Who are you, and why are you doing that to me? You’re not supposed to do that.’ It was not in my radar.

Why did you think she wasn’t supposed to do that?

Probably because of my mother’s notion of nobody’s supposed to kiss you other than your family– that was definitely taught to us about strangers not kissing you, that whole thing.

What messages did you get from your mother and father in childhood about sex and girls?

I remember those conversations about strangers, “Stranger danger,” and all that kind of shit.

As part of the stranger danger talk, there was talk about physical contact?


Tell me what they said.

They didn’t say much about it, just that strangers aren’t supposed to touch you. It’s ironic that they said that. My brother was heavily abused by a neighbor kid. It came out later. We’ve all learned.

As you got older what are the messages you heard from your parents about sex, spoken or unspoken?

It was more about pregnancy. It was more about, “Don’t get a girl pregnant.” There wasn’t a lot about it. In high school there was sex ed. Obviously I learned more about sex through experiences than through sex ed. I learned about the reproductive system for sure through sex ed, but I was sexually active very young.

Growing up, what did you think your parents wanted you to do around sex?

I don’t know. I think they knew it was going to happen, but the less said about it and ‘just figure it out on your own.’

Did you ever feel like you weren’t supposed to have sex according to them?

No. I mean my mom tried to preach that, but I just never listened. There wasn’t a lot of respect there about her religious beliefs, so that just wasn’t in the cards for me.

What were her religious beliefs?

Very Christian.

Why didn’t you respect that opinion of hers?

I just thought it to be very hypocritical.

How so?

My uncle, her brother, is a preacher and maybe the most crooked human being I’ve ever met in my life. He stole all the family’s money when I was very young. It was just a dialogue about him constantly. Things that just shouldn’t happen if you’re a good Christian. From that point, I was just like, ‘This guy’s telling people how to live?’ It just doesn’t make sense.

Did you get any messages from your father about sex?

Don’t get a girl pregnant. I learned a lot from my dad about how to be a gentleman, and how to treat women, and how to protect women. I give him a lot of credit in that area for sure, but the discussion of what sex, and that just — it makes sense, knowing how he grew up. He did better than his parents for sure. I don’t have any resentment for him not doing that.

. . .

Tell me when your first sexual experience with a girl is?

Okay, I was 14. It was the first kiss. It was the first everything. I was 14, and ironically, it was my cousin. She was 22. We went to visit them in San Diego. Everybody would go to bed, and we would get together and have fun.

Tell me, if you can in detail, how it starts the first time? What you do? How it feels?

The first time I heard her. She was out with her friends, and she came into the house. It’s probably 11 o’clock at night. I was sleeping downstairs, and I heard her come in. I was waiting for her to come home.


Because I was totally attracted to her, and over that summer I grew like eight inches and was 6’1”, not fat. I had become a different person. I was confident. Everything changed for me at that point. I waited for her to come home and laid there for awhile. I’m like ‘Oh my God, am I actually going to like’ — running through me head the nerves I was having about wanting to go up and go in her room. Then I just mustered up the strength. I just went up there and opened the door and slid into her bed. She asked ‘What are you doing.’ I said ‘I want to spend the night in here with you.’ She said okay and instantly started making out. I was just like ‘Wow.’ That was better than I thought it was going to go. Yeah, nothing sexual happened that first night other than heavy petting.

How was it to kiss and touch a girl for the first time?

Ooh, man, unbelievable. It was unbelievable. I thought I was going to have an orgasm actually. I was laying there, kissing her, and feeling her breasts, and I had never done that. It was, yep, amazing.

Then what happens with her?

The next day, heavy flirting throughout the whole day, and then that next night, the same thing. Everybody went to sleep, and I snuck up there again; more kissing, and kissing her breasts, and then I got my first blow job. That was like, forget it. I don’t even know what to say about that. I was like, are you kidding? The next day, same thing; the next night –

Let me ask you about the blow job. Did you by this time know that blow jobs happened?

Yeah. I had heard from friends at school that had either talked about or seen porno magazines. Friends’ dads had Playboy around. Magazines, and just the dialogue of friends changed.

What was the talk among the boys about sex?

I hung out with a lot older guys. I raced professional motocross. I was at the track 5, 6 days a week. All my friends at that time were 17, 18, 19. I overheard. They come to pick me up to ride every day. Then my brother, I’d hear stories from my brother and all his friends. It was just an ongoing dialogue from guys in my life.

What were the stories like?

Looking back, crude, really crude, not very respectful of women in their lives.

How did those stories feel to you at the time?

Probably okay because that’s all I knew. I didn’t know that wasn’t — I didn’t know any different.

Do you think that being the way you got information about sex affected how you approached women and sex?

Before I had sex, yes.

Why did it change once you had sex?

Because that week of being with my cousin, which sounds really fucked up — really fucked up — but hey I’m here to be honest, right?


It was just more than just an orgasm.


Because I really liked her, and I really liked hanging out with her. She was a nice — she’s an extremely nice woman. She gave me a gift. She was the first one to give me a gift. I guess not gift, but it felt like it was a gift. It felt very gracious and loving and teaching. That experience set the tone for my life sexually for sure.

Going back to that week, the second night you get a blow job.

We had sex. She was on top, and she was basically telling me exactly what to do.

How did you feel about her telling you what to do?

I loved it, loved it. It wasn’t dominating, but it was definitely teaching and taking her time. I mean it felt like forever, but I’m sure it was three minutes. I orgasmed and then that night was over.

Do you remember what she told you to do specifically to her, for her?

Yeah, we were making out. I was sucking on her breasts. She was on top of me, and I was underneath her sucking on her breasts. Then she said ‘Kiss me,’ and we kissed. Then she sat up like she was going to get up. I was like ‘What’s going on?’ Then she told me to grab my cock, and I grabbed my cock. Then she got up on her hands and knees and just slowly slithered down my cock, and then just kind of ground herself into it, then came back down. She said don’t move for a second. Then she told me things like ‘Let me do this for a second.’

I just laid there, and I was just thinking to myself, ‘Holy shit. I’m having sex for the first time. I’m inside her right now.’ Then she sat up, and she wanted me to suck on her tits again. Then she started faster wiggling her hips. She said ‘Don’t move, don’t move.’ She just kept telling me ‘Don’t move.’ Then she came back down and was on all fours. Then she said ‘Okay. Now slowly start fucking me’ is what she said. It was like two strokes and I was done. Yeah, woo, that was fun.

How did you feel after that?

Oh, man. I was consciously thinking ‘I just fucked my cousin.’ Then my ego was taking over saying ‘You just fucked a 22 year old. You just had sex with a 22 year old girl,’ which this was no nerves around it and no — yeah, it was just — I felt like it was just awesome.

Why were there no nerves around it do you think?

No nerves from her. I had heard stories about other girls losing their virginity to a guy their same age or whatever, how nervous it was and how it just wasn’t fun.

For the guy?

Or the girl.

Okay, guys were telling you that they were having sex with girls who were virgins, and the boys were feeling like she wasn’t having a good time?

Yeah, yep.

When you heard those stories from other boys, what was the attitudes of the boys telling it?

They were bugged. They were trying to — there was obviously ego trying to show off. They popped a chip on a girl, and she was just a fucking dog or whatever the dialogue really was. How shitty it was and how it wasn’t fun. It’s pretty much just ego-driven dialogue.

If we put it in adult terms, her lack of pleasure reflected poorly on how he felt about his own experience?

Yeah, yeah.

After you have sex for the first time with your cousin, what happens next?

We ended up having sex until I went home; every night, different positions, and ‘Here’s how you do this, and here’s how you do that,’ a lot of dialogue of teaching how to have sex.

How do you think this experience with her impacted your future sex life?

I love older women, always have. Yep, love older women.


All the sex I had with younger girls, they weren’t ready. They might have thought they were ready, but they’re not. What I’ve learned now about older women, they’re into pleasing themselves as well. That is definitely something that young girls don’t do. They might do it on the side, but they’re not having sex with you to pleasure themselves. They’re having sex with you to please you. That’s very obvious.

When I was 15, I was having sex with one of my friend’s mothers. That was unbelievable, same situation. She was in it to win it for herself too. I don’t know. I feel really bad for young women. I’m happy you’re doing this. I have two daughters. We talk to them in ways that I was never talked to for sure. I hope they realize that you don’t have to do that for them.

What would you tell your daughters about sex and pleasure?

That you need to be selfish as a woman. Women aren’t selfish enough in that area at a younger age. Older women are much more selfish, which to me, turns me on that much more.

Why does it turn you on?

Because they’re comfortable, and they want to do things that are pleasures to them. The dialogue, they can talk about it too. There’s no ‘Here’s what I like. Can you do it this way? Can you do it that?’ Of course I can. It’s very one-sided at a young age.

When it’s one-sided, how does that affect your sexual experience?

Not good.


Because it’s just not a whole. It doesn’t feel like a whole as in a circle whole, as in two bodies coming together. Because I had the experience of that so young. When I had sex later that year, I was a girl’s first. It was just a completely different thing.

I wasn’t in the position to teach her how to do it. She really wanted to have sex for her first time with me, but it was not a good experience.

For you or her?


How do you think she experienced it?

Pain, guilt. I definitely didn’t handle it very well either.

How did you handle it?

Probably with too much disrespect post sex. I definitely told my best friend, and she didn’t want anybody to know for some reason. I wasn’t great in that way, and it ruined our relationship.

Did she find out that you had told people?


Why did you tell your best friend?

Ego, definitely ego and wanting to brag and wanting to be stupid.

How did you feel exactly about that experience right afterwards? What did you feel about yourself after that?

I definitely felt guilty. I definitely had guilt because it was so unpleasurable for her, and I liked her. She was my girlfriend. She was important to me. I’d been dating her for a month and a lot of kissing and a lot of heavy petting. I probably talked her into doing it. I can’t remember what the dialogue was. Then she did not like it and was in a lot of pain. Looking back, I probably should have just held her and said it’s okay, but that wasn’t where I was at, wasn’t mature enough to go there with her.

What happened after you had sex?

We just put our shit on and just walked out. She said ‘I got to go home,’ and she just left.

After that, did you continue having sex?

With her?



Why not?

We broke up shortly thereafter. She felt disrespected due to me telling my best friend. I probably didn’t treat her that well post-sex. She felt like I was just in it for the sex.

How did you actually feel about it?

I actually liked her. I really liked her. I still like her today. No, I thought I was in love. I didn’t know how to deal with the uncomfortableness that she was having. I almost want to go up to all the dads that’s with the boys and go ‘Hey here’s what I did. Let’s talk to your dudes that are 14 about this shit.’

If you had a son, what would you tell him?

I would tell him all this. I would be blatantly honest with him and tell him exactly everything that I did wrong. Hey, I’m still learning. I feel like if I don’t learn something new every day, I’m going backwards. I would definitely tell my sons everything. I don’t know, make them sit down and go ‘You’re not leaving. You just got to listen. Here’s where I fucked up.’

. . .

What happens after your first girlfriend?

Nothing for awhile and then my third experience was my friend’s mother.

Tell me how that comes to be.

He was a fellow racer. He was a few years younger than me. Single mom — I used to spend the night at their house all the time. He’d spend the night at my house all the time and go ride the next day. It was pretty much the same scenario as the cousin. My buddy went to sleep. She was still awake, and I just went out there and made the move. It paid off. That went on for months.

How old was she at the time?

She was 30, maybe.

You were?

I was 15.

Do you remember the first time you had sex with her?

Yes. It was that night. I remember what she was wearing. She’d walk around the house in underwear and white tank top. You know, just constantly flirting and saying how cute I was; maybe inappropriate, obviously inappropriate, now that I look back. Yeah, she was hot. I just went in there and grabbed her and started kissing her. I didn’t say anything. I just walked in there and laid one on her. Then it was just on. We just went into her bedroom. Yep, it was a similar situation where she was telling me what to do.

Did she teach you anything new sexually that your cousin hadn’t?

Yes, oral sex.

How did she teach you oral sex?

After four or five times of standard sex, then she was more comfortable asking me questions. ‘Have you ever done this?’ ‘No.’ ‘Have you ever done that?’ I really didn’t like it, but I realized that she did. I was just honest. I was very honest with her and said ‘No. I’ve never done that.’ She goes ‘Are you willing?’ I said ‘Sure.’ I gave it a try. She gave me direction, definitely, about what to do. Do you want detail on that?

Yeah, detail’s good.

She wanted me to spread her lips, and lick all the way up one side, and then all the way up the other side, make circles with my tongue around the clit. She just said ‘Okay. Now just do that more.’ Then she would say ‘Okay. Now just lick my clit.’ She taught me about the pussy, the parts of the pussy. I didn’t really like it, but I saw the outcome of what it did.

What was the outcome?

Her orgasming.

How was that for you?

Crazy, crazy, crazy because she was very loud and very free. She was very talkative.

How did that feel for you?

It felt unbelievably good.


Because I did that. That seemed like a full blown accomplishment to me. I’d never seen a girl orgasm before. Looking back, my cousin definitely didn’t. She probably wasn’t comfortable enough with herself to. That was the first time I’d seen a woman orgasm. It was crazy, crazy, crazy.

Why didn’t you like going down on her?

I don’t know. I just didn’t. The idea of it just seemed completely wrong to me.

Wrong in what sense?

The taste, and I’m not supposed to be down here with this part of my body. Probably because none of my friends — none of my older 17, 18, 19-year-old friends had ever talked about that.

The more I reflect on that, they didn’t give a shit about them. They, unfortunately, at that age still hadn’t probably experienced a girl orgasming because they weren’t willing to go there. It was all about them. I feel really fortunate that I had that experience because from that point on it changed my entire outlook. Now in my life, I would much rather make people come than orgasm myself. It’s a huge pleasure to me, for me, and has been since that day. That boosts my ego more than anything.

Did you know that women could orgasm before that moment?

Yeah. I had no idea how they did it because I didn’t have sex-ed until I was 16 in high school. She taught me that about the clitoris. ‘This is the part that makes me do that kind of stuff.’ Once again, it was a fucked up relationship. She should have never done — you’re 30. You shouldn’t be fucking a 15 year old, but it taught me a lot.

What were your feelings around the pussy as a teenage boy?

It was a mystery. It was a real mystery. There’s a lot of parts. That relationship taught me a lot about all the parts. Before it was like ‘Okay, that’s where my little sister came from. I don’t even want to see that. Get that away. You can’t be naked.’ Because it was my mom, ‘Go away with that thing.’

How does that relationship progress, the one with the mom?

The son would go spend half the time with the dad. I would lie to my parents about. I’d call over there and know he was gone. It was like three miles away. I’d ride my bicycle to his house; spend the night with the mom. My parents thinking that I was spending the night with him.

You spent a lot of time together.

A lot of time, a lot of time; yep, one or two days a week during summer. That went on for six, seven months.

That’s a lot of sex.

Lot of sex.

How does the sexual relationship progress? What does she teach you? What are the emotional components? What happens in that relationship?

There wasn’t a lot of emotional components to it. It was all just physical sex. It was a completely different feeling emotionally than it was with my cousin or with my girlfriend. I had feelings for those people. This woman, it was strictly physical sex and wanting to learn more.

How do you spend that much time with someone without developing feelings?

The thing I realize about that relationship there was never really any kissing. We never embraced in that way or held each other in that way. It was all probably semi-dominant, maybe, on her behalf. Used me and go away.

That’s how it felt to you?

Yeah, but I didn’t mind at all. I was having sex and learning about sex and fucking in all different kinds of ways. I was becoming a sexual being.

For you it felt like a useful learning experience as well as pleasurable?

Using me maybe, I was using her. I don’t even remember giving her a hug goodbye and just saying I’ll see you later. I don’t remember any love.

Do you remember wanting anything more from her than you were getting?


You didn’t get the sense that she wanted more either?

No because it was super sneaky, and I was lying to my parents constantly about it. I didn’t feel great about it because I’m fucking my good buddy’s mom, but I did feel great about it. I wasn’t willing to quit for that.

It felt like a betrayal of your friend?

It felt a little shitty.

How did you feel about the dishonesty with your parents?

I didn’t care about that at all because it was all about me, me and my ego.

What else did she teach you sexually?

It was more about slowing down.

Tell me more about that.

I still have a problem with that. It was all about her. The second I was selfish she was like ‘No. That’s not happening.’

Tell me. Give me an example of that.

I mean, that was my first doggy style experience, and I wanted to fuck her. Go for it and fuck her. She didn’t want that, and she let me know immediately. ‘You will stop doing that right now.’ Yeah.

How did you feel about that in the moment?

I felt, ‘Okay, I’ll be a dog.’ I didn’t want to fuck it up because I’m getting laid, and this is better than anything I’ve got going anywhere else.

She was very intent on her pleasure and making sure that you were focused on her pleasure?


How did that impact your future sexual self, or did it?

I really enjoyed being told what to do. I’ve been telling the ones I love that. They just can’t fucking do it. I mean, that is definitely what I fantasize about. Not that I want to be dominated. I’m a very dominant person, so to have somebody else tell you what to do in that way is very sexually intimate.

From the beginning, it sounds like maybe you knew it had to end. Every time you did it you were like, ‘Uh-oh, is this the last time?’

When I got there, it didn’t feel that way. She would say ‘Okay. Yeah, come by.’ I’d be like, ‘Oh, great.’ Then I’d get there, and it’d all be good. Then we had sex, and then when I would go to leave, I always rode my bicycle home in a weird fucked up mood. It was never like, ‘Wow, that was great!’ I always left a little empty just because I never felt any love from her. It was an empty relationship other than getting each other off.

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