by Mike

Gender: Male
Age: early 40s
Race/ethnicity: Mixed
Location: Denver, Colorado
Highest education received: College degree (eg., BA, BS)
Occupation: Law Enforcement
Relationship status: Divorced
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? One

My Public Assistant

How long ago did this hookup happen? Eighteen Months

How would you best classify this hookup? Fuck Buddies/Couple/I am Not sure

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? Chelsea is a public assistant or PA at the station where I work. She’s in her late twenties, tall for a woman, five nine or ten with legs that don’t quit. She is also skinny but has a big chest and she is almost thirteen years my junior. She is also quite intelligent, I have found I need a bit of an intellectual attraction to women as well. I had shown her around when she had first started working here, and Chelsea has since admitted to having had a big crush on me then and really liking me, but back then I was still married but she knew I would never cheat on my wife. I liked her and was always friendly with her before we started going out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Without repeating many of the same details of my last post (See My Ex-Wife) following the loss of my partner and my drinking too much and her affair, my wife and I split up about four years ago, the divorce was finalized a year later. I spent over two years moping around and mostly working. I dated a few women casually, one of which I think was looking for me to fuck her one night at her place but was just not ready. You don’t just get over fifteen years with someone. Other than my ex-wife there was only one other woman I had ever been with, a fellow soldier I saw for a few months early in my Army days. My number is far lower than many men my age.

Back to Chelsea now, she had stayed away from cops and not dated any even though she got hit on a lot. Cops are hound dogs, having worked around them for close to 19 years I know these things. Chelsea said she gave me a lot of time after my divorce but she began to wear shorter and shorter skirts to work and lower cut tops to catch my attention, to the point the Captain told her to change how she dressed. She came to my desk a lot and bent over so I could look down her shirt and I had noticed how toned her legs were.
Finally Chelsea worked up the nerve and actually asked me out. I agreed, and we went to the gun range for our first date. Despite more than five years around cops, Chelsea had barley fired a gun. Second date was dinner, so was the third. We had kissed on our second date, and the third we had been flirting a lot and we made out a bit and ended up back at my apartment. I found myself very attracted to her.  
We were making out on my couch and Chelsea went to use the bathroom. She came out minus her skirt and several buttons down on her blouse to where she was showing a lot of cleavage and  a little bit of bra.

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? Chelsea asked me to sit there and undid my belt and before I could ask what she was doing she had her mouth on my cock. She licked and sucked it, and even deep-throated it a bit. It had been a long time since someone other than me and it felt amazing. I came in her mouth and we moved to the bedroom and Chelsea went to the bathroom to rinse her mouth out.
I am not as young as I used to be, it takes me a while to be able to go again. We decided to go with some foreplay and made out some more and felt each other. We took our clothes off, and Chelsea had on a black lace bra and panties set that was fun to remove. She had a lot of tattoos, both hips, on her right breast, both shoulders, on her back and even a tramp stamp which she said was a mistake in college.  She also had one on her thigh which I really like. I like my women inked up, my ex-wife has a number of them too. Chelsea is also quite toned, even a little muscular from working out and she also has a pierced navel. Overall she is smoking and really something to see nude.

I took her bra and panties off and saw her boobs for the first time. I am a leg man, but I like boobs too.  They were quite large and fake (34DDs I learned when I bought her some lingerie later) and felt a little weird, a little hard, since I had never had my hands on fake boobs before. I licked and sucked them, Chelsea really liked that. We decided to have sex, and Chelsea wanted me to take her in doggie. I did, put my hands on her hips and it was a lot of fun. She was quite loud and screamed a lot, and also orgasmed after just a few minutes. Took me a while to again but I did as well. We were both quite tired after this and fell asleep.
Next morning she was still over and we had sex again, this time with her on top in what I think is called cowgirl. I kept grabbing her boobs which she liked and she would lean down to kiss me repeatedly. We both orgasmed close together.
We took a shower together, a lot of kissing but no intercourse and Chelsea left and went home shortly after.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Other than my ex-wife there hadn’t been anyone in close to eighteen years and Chelsea had recently tested clean and she was on he pill. We talked about it but did go bareback.

What were your REASONS for having this hookup? A very long time without sex and I am very attracted to Chelsea.

Were alcohol or drugs involved? If so, how much? I had a beer at dinner, Chelsea is from a family of alcoholics and won’t touch booze 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? Chelsea and I have kind of been on again, off again for the last year and a half. In the bedroom she is a lot of fun, I have gotten her to where she likes missionary and we also like reverse cowgirl her favorite position. Outside we go to movies, have dinner, go shooting, normal couple stuff. We have also had some off periods were we are broken up.
I could easily see a future with Chelsea, I have strong feelings towards her now. However there are two issues, first the last serious boyfriend Chelsea had was abusive and this has left her a little damaged emotionally and somewhat hesitant to truly connect with me. She once thought I was going to hit her during an argument which actually hurt me a little. As far as I know all couples fight. The other issue is the age difference, not huge but I know Chelsea wants to have children. I have two teenagers from my marriage and I am not sure I want more kids.
As for how I feel about her now, currently we are in an on phase again. I would really like to pursue a serious relationship with Chelsea and I am trying to figure out how to approach her about it.

To whom did you talk about the hookup? How did they react? A few colleagues who were impressed, as I said cops are hounds. My ex-wife is still quite jealous which I have to admit I am ok with. My kids are not sure what to make of Dad’s much younger girlfriend although I wouldn’t necessarily use that term to describe Chelsea.

Was this a consensual and/or wanted experience for you? For your partner? For me yes and since Chelsea initiated most things I am assuming for her as well.

Do you regret this hookup? If so, why? Not at all

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? Great sex with someone I really like and am very attracted to. Worst part has been dealing with both mine and Chelsea’s emotional baggage. I did learn women can initiate and really enjoy sex. I feel a lot better about myself since I started sleeping with Chelsea.

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

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

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