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What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +50
How many hookup stories have you here posted before? 0

MILF Co-Worker

How long ago did this hookup happen? couple of weeks ago

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For 1 to 3 years

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? Brit has been my partner with a mobile medical company for over a year now. She’s an RN, mid 40s, natural blonde hair, hazel eyes, 5” 8’, maybe 120 lbs, size C or D fake breasts, and a southern smile that will make your heart melt. She’s from South Carolina originally but her husband’s job forced them to move to this area. She has two teenage boys, and for her age, she’s a stunning MILF!

In the past year, we’ve gotten to know each other well. I’ve shared stories about the women I hook-up over the weekend and occasional girlfriends. She’s shared stories about her husband’s busy job and the sports her sons play. I noticed early on that she doesn’t mind my flirting or eyes wandering. She caught me checking her ass out the first week we were together. She wears fitted scrubs, and I think she has a very nice firm and round ass. I was being obvious when she caught me and was expecting a tongue lashing or reported to HR, but she just smiled and went on. I started out complimenting her fit body and how she makes medical scrubs look sexy. She always smiles and say thanks. She soon began complimenting my muscular arms and chest. We never went overboard with the flirting, but I could tell she liked the attention.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Fourth of July was coming up and I asked what her plans were. She told me her husband was taking the boys backcountry camping and fishing. She was supposed to go shopping in Atlanta, but her friends canceled and she would be staying at home. She sounded bummed when she said, “Looks like I’ll be cleaning out the garage and attic.”

I invited her to my apartment complex for a cook-out at our community pool area and to watch fireworks from my balcony on the 3rd floor. She was hesitant at first, but I convinced her it was a family event and not a bunch of former frat boys partying. She asked, “Don’t you have a date lined up?” I quickly replied, “I’m asking a beautiful women right now to be my date.” She playfully pushed me and agreed to stop by, BUT only for a couple of hours.

She arrived wearing a knee length denim skirt, tight white tank top, and flip flops. She began talking to my neighbors and was having a great time. As it started getting dark, everyone began to clear out and I invited Brit to my apartment to watch the fireworks.

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? We stood on the balcony and I put my hand around her waist. She put her head on my shoulder. We both kissed as the fireworks began. Things were getting heated so we went inside to the bedroom. She pulled my shorts down and started sucking me. I pulled her shirt off then she slid out of her skirt and white cotton panties. She had a thin maintained bush. I offered a condom, but she declined. I laid on the bed and she got on top. She was already so wet and I went inside her easily. I squeezed her fake tits as she fucked me. It didn’t take her long to orgasm. We changed positions, me on top. She told me she had her tubes tied and gave me permission to cum inside. I started out fast and hard, but I was trying to make the moment last without getting off too soon. I couldn’t hold back and I began filling her full. She leaned up, pulled me down and started kissing me passionately with tongue as I was cumming inside her. She ran to the bathroom afterward to clean up, and I thought she was going home. Instead, she got back in the bed with me and we kissed and had sex again. She spent the night.

The next morning, I woke up and she was walking around wearing the white tank top and white cotton panties. She stayed for coffee. She could tell I loved looking at her body. She was about to leave, but she looked at my crotch and noticed I was hard. She took off her panties and pulled her skirt up and bent over the couch and said, “Be quick.” I grabbed her hips and fucked her until I came inside her again.

She went home to do some stuff around the house but agreed to come back that evening for dinner. I told her about a seafood restaurant that’s a couple of streets over that we could walk to. My intention was to have dinner, but I was also hoping we would have sex again. I didn’t know how she would react after she had time to go home and think about last night.

She arrived and she’d spent time with her hair and make-up. She was wearing a conservative knee length dress that zipped up the back. I made plenty of comments about how HOT she looked. I’ve made sexy comments to her before but this time she blushed. We walked to the restaurant & she reached out and held my hand. After dinner, we walked back to the apartment. Instead of stopping by her SUV and telling me ‘Bye’, she followed me back to my place. We got inside and began kissing. I unzipped her dress and it hit the floor. I stood back in amazement to admire her body wearing a matching black lace bra and thong panties. She smiled and said, “I wasn’t prepared yesterday and felt bad you had seen me wearing cotton ‘mom’ panties. (she turned around) I thought you might like this better.” She was horny last night so I thought I say something she would love to hear. I said, “I love it. BUT I really loved waking up and seeing you all natural, wearing cotton panties and a tank top. I wish I could see that every morning.” She blushed and gave me a kiss. This time I started by giving her oral. Today, she was smooth shaven and when I started, she wrapped her legs around my head and pressed my face against her as I worked my tongue. She made me stop me and begged me to fuck her NOW! We had sex a couple of times and I begged her to stay the night, but she couldn’t because she didn’t know what time her husband and boys would be coming home the next day. She left after we were both spent.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Things were normal on our first day back to work. For lunch, we got sandwiches and went to a park. She told me she has no regrets because her husband has not given her any attention in months. She added, “when I say ‘no attention’ I mean NO sex” she held my hand and thanked me for being a gentleman and respectful to her this past weekend and not treating her like a ‘notch on a bed post’. She doesn’t want a divorce but would like to continue what we have. Now I knew what she was craving, attention and sex. I knew this would get her back to my place again. I said, “You are a wonderful, beautiful person. The best part of the weekend was having dinner and waking up with you at my place. The sex was great and you have an amazing body, but I enjoy spending time with you too.” She blushed. I knew it would. She put her hand on my crotch and I was hard. She promised we’d hook-up again but it will take good scheduling.

We haven’t hooked-up yet, but she keeps giving me updates when her husband will be away soon and is trying to have the boys stay at friend’s house. I suggested we both take a vacation day, and she can act like she’s going to work. I’ll post an update if it become more than something regular.

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, Attraction to partner(s)

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

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

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A friend I golf with. I showed him a photo of her on my phone and he agreed that she’s a MILF.

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? Finally getting to have sex with Brit. We’ve flirted for so long and I’ve always wondered how she would be in bed. I’m impressed!

Seeing her wearing a white tank top and white cotton panties. The image stays with me.

What was the WORST thing about this hookup? We haven’t hooked-up again. I believe we will hook-up but not as often as I would like.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The way I think about casual sex has remained the same. I’ve never been in a long term and serious relationship. Most girls my age have drama and are looking for something short term. I’ve hooked-up with women 10 years older and my experience is they know what they want and are more aggressive in the bedroom.

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

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

Anything else you want to add about this hookup? Brit is the oldest woman I’ve had sex with and I rank her at the top of my BEST EVER list. Proof age doesn’t matter.

I told Brit I would never expect her to quit her marriage and I’m willing to be as discrete as possible if we continue hooking-up. All I want is for both of us to become close friends, have dinner dates on occasion and amazing sex afterward. She told me that’s all she wants.

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? This is a reason I have no intention of getting married. I’ve gotten to know Brit well over the past year. I think she’s a great mom, still attractive, a caring personality that everyone loves and she’s been loyal to her husband (until now LOL). Now, her marriage is stale. Her husband won’t give her attention and she’s made attempts. People in relationships get bored with each other and it should be acceptable to have casual sex. Brit is still interested in hooking-up with me again but is cautious her husband will find out. Society puts that thought in our minds when it shouldn’t be that way. If Brit is not getting the attention and sex at home, she should have the option to fulfill her needs without worry of getting caught or being forced into a divorce. People in committed relationships have sex all the time but must remain discrete because of society.

What do you think about the Casual Sex Project? Good place to add a life experience.

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