My Son’s Mom

by Nick

Gender: Male

Age: 35 Now, 25 Then
Race/ethnicity: White
Location: Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Criminal Psychologyst
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? One

My Son’s Mom

How long ago did this hookup happen? Eleven Years Ago

How would you best classify this hookup? Sex with an Ex

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? I’ll use this section to share about my history with Lindsay, the mother of my son. In High School, I was two years younger than the other students and in college I was focused mostly on my studies and not much on girls. That is not to say I didn’t have sex. There were a few coeds and I did have an affair with one of my professors, adding that story to the list of hookups I will share, but no one truly special.

The town where I went to college consisted mostly of two groups, college students from the University, and Army personnel from the base North of town. There was a coffee bar popular with both, I was only 20 then and too young to drink, and I went there for a break from a long study session needing to go over some research towards my Masters.

That was when Lindsay walked in, a pretty brunette in fatigues. Women in uniform get me off, always have, but she was the first. She had long legs and I could only check her ass out a bit in fatigues but my guess was she had a pretty good body under that uniform. I decided to give up my studies for a short time and go talk to her. I introduced myself and sat down and we started talking. We actually had a lot in common, we were both from small towns and Catholic however her upbringing was a lot stricter than mine. Lindsay had a weekend pass off base and was spending a little time in town. We talked about my research which she found interesting, and we flirted a bit. Lindsay was 19, a year younger than me and had only finished her basic training a few months prior.

I won’t deny I went there looking to get laid that night, the place had a reputation for that with the students. With Lindsay’s upbringing had she known that, she would never have gone in there. However I quickly figured out that there was no way Lindsay would sleep with me that night but there was such a connection that we talked until closing anyway. She did kiss me and give me her number. I decided I wanted to pursue and date her but I was also determined to bed her. I have always enjoyed a challenge.
I did bed he a month later, Lindsay was a virgin and has been the only woman I ever deflowered. Not sharing that story, it’s just too private. Lindsay and I were a couple for a little over three years ultimately, and we had a lot of sex. Once opened up, she was very sexual. I won’t deny I fell in love with Lindsay.

Lindsay and I were together a little over two years when she got orders to a base in Germany. 9/11 was still about seven or eight months out when we heard and Lindsay was looking to go to Officer’s school and needed some overseas duty to round out her resume. We weren’t married so I couldn’t take time off and go with her, and I was working towards my first PHD at the time and Lindsay did not want me to screw that up.

The next few months were brutal, the distance hard. Back then there was no Skype, phone calls overseas were very expensive, but we were able to email several times a day. I was able to visit for a week, one of my professors took me along to a conference because he was tired of me being all depressed and pathetic. Won’t complain too much, he is a really good guy and we are still in touch. Anyway Lindsay and I did make love a few times and we had missed each other.

Lindsay came home about two months later, her tour up. Her last few emails said we needed to talk and when we met she confessed she was ten weeks pregnant. Lindsay had been forced to briefly go off the pill because of possible interactions of another medications he had to go on. The timing was certainly right from when I visited her in Germany. She was very nervous about telling me but I was thrilled at the prospect of becoming a father.

With our upbringing abortion was never an option and I made the decision to do the right thing. I was already planning on asking Lindsay to marry me once she settled back in but this just made me decide to do so sooner than I had planned. I started ring shopping.

However things imploded quickly after that. A few days later Lindsay confessed to an affair with another soldier on base while in Germany and she was not sure the baby was mine. I lost it and we had a huge fight, for the record still the worst I have ever had with a significant other. I swore at her called her a whore and a lot worse, finally I stormed out of our place a little worried what I might do. We decided to break up a few days later and Lindsay moved out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I decided I wanted to be there for the baby, and Lindsay had our son about seven months later. He had a paternity test shortly after he was born, Lindsay wanted to make sure if he was not mine she could go after the right guy. He was mine though.

I was around a lot, the pregnancy had been pretty brutal on Lindsay and she needed help and I didn’t blame my son for what had happened between me and his mom. I was single a long time, never having more than a few one night stands, but I did eventually start seeing a tattoo artist.

The artist and I just split up, and I was a little upset about that. I had stopped by to spend some time with my son and Lindsay was there. It had taken over a year but we had worked back to the point we were friends.

I put our son down for a nap, and Lindsay was in her bedroom. I had gone to talk to her, opened up a bit about my recent breakup and she was single. I could always talk to her. While I was no longer in love with Lindsay, I still had strong feelings toward her. She is my son’s mother. Lindsay started massaging my back and then kissing it. Eventually I brought it around and sat her on my lap and we started kissing and making out.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Lindsay told me to take my shirt off and she went into the bathroom. She came out in nothing but her uniform blouse and skirt, with the buttons open well past her breasts and I could see she had taken her bra off. Two things got me really going, women in uniform and breasts and Lindsay knew this very well. The plus side of sex with an ex is we both knew each other’s likes and dislikes in the bedroom very well.
She pushed me down on the bed and began to kiss me and then down my neck and chest. She licked and sucked my nipples for a few minutes before sitting up and I removed her blouse and she was now topless. I pulled her skirt own and she was now standing there nude.

Lindsay was a little rounder than I remembered, still having a bit of baby weight despite how much she had been working out. I actually liked the change, she had been very fit when we had been dating but she had hips and a booty now. Her breasts were also a significantly bigger and I was hardly going to complain about that. However she did have some stretch marks on her stomach and breasts.

I laid her down on the bed and kissed her, then worked my way down. There was a spot on her neck Lindsay had always liked me to kiss. I spent some time on her now magnificent breasts, licking them and sucking them like I always had. Her nipples were a little tender and I got a little breast milk in my mouth which today I still feel weird about.

I decided it was time and put my cock in her, she had delivered via C-section as evidence by the scar on her midsection, so she was intact down there. My cock was always a good fit for her and I started riding her I actually came what was quickly for me back then, just about ten minutes. I was a bit embarrassed and Lindsay was very disappointed, she had wanted to be rode for a long time.
Lindsay had always required a lot of foreplay to orgasm, so after I relaxed a few minutes I reached over and fingered her until she began to moan loudly and came.
We both laid there a few minutes in post sex bliss. Finally Lindsay climbed out of bed, went into the bathroom and came out in sweats. She said I needed to leave and kicked me out.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Considering Lindsay’s sexual history was me and one other guy and she was back on the Pill, we had discussed it about a month before, this was a rare occasion I was comfortable having unprotected sex with someone.

What were your REASONS for having this hookup? I was feeling lonely and Lindsay was someone I once had strong feelings for.

Were alcohol or drugs involved? If so, how much? Not at all

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? The hookup brought up a lot of feelings for both me and Lindsay and we discussed getting back together – something we had done before and would many more times over the years. People used to ask me why we are not still together but I could never get over the betrayal of her cheating and completely trust her and we agreed this meant we could not be a couple again.

Next seven years or so Lindsay and I had a pattern of hooking up four or five times a year if we were both single. It was mostly just sex though. Lindsay was single for many years though, few men want to date a single Mom. However Lindsay did eventually get involved with someone else, actually a really good decent guy but I can never admit that, and got married last year.

We talk all the time because we have a son together however it is not as easy as it once was. Shortly after she married Lindsay was promoted to Major and the only openings were overseas so she was forced to relocate with her husband and our son. I also heard she is pregnant again. I am actually quite happy for her and there is always a place in my heart for her. Lindsay will always be the mother of my son and the first woman I ever loved.

To whom did you talk about the hookup? How did they react? My roommate who thought it was a bit of a mistake considering our history.

Was this a consensual and/or wanted experience for you? For your partner? We both wanted this very much. I was lonely as I said and Lindsay confessed after to being very horny.

Do you regret this hookup? If so, why? A little, this brought up some confusing feelings for both me and Lindsay.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Sex with an ex like Lindsay is usually great, as this is someone who knows you well and is familiar with what you like in the bedroom. The worst were the buried feelings it brought up. I learned casual sex was a good thing and had thought it near impossible before this. I always felt good about myself after Lindsay and I would hook up.
I did notice reading this post over that I used terms such as bedding and made love when it came to Lindsay instead of screwed and fucked. I think that showed things will always be different between me and Lindsay.

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

Anything else you want to add about this hookup or anything else? Have a few stories I can contribute to this, see The Cop, that I will be adding as I have time.

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