Christmas Eve Fling

This post is sponsored by Trust Massage Oil.


What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Philadelphia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
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)? 20
How many hookup stories have you here posted before? 1

Christmas Eve Fling

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? Denise had joined the multimedia team that I was on at church. She was recently divorced and had joined to help her make new friends. I helped train her on the computer system and found out we had several of the same hobbies. One of them was photography. She was about 5’7″, slender, big smile and red hair. I have always been attracted to red heads, so i was definitely attracted to her. We kept it friendly between us. I didn’t sense any flirting between us and thought it would just stay that way.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Flash forward to Christmas time. It was my turn on the work rotation to work Christmas day and the few days after at my job. Since my father in law was in bad health, my wife decided to fly her and the kids down to see her parents over the Christmas holiday and leave me home to work. I volunteered to work the some of the Christmas Eve services at our church. Denise had signed up for the same services. When Denise walked in the building, my eyes instantly went to her. She was wearing a tight red top, black skirt, black pantyhose and black knee high boots. She was never that dressed up before. I asked about why she was so dressed up and she said she had to go to her brothers house afterwards. Her sister in law always threw a big Christmas Eve party and everyone was expected to dressed up.

I had trouble not staring at her during the services. She looked amazing, During out breaks we talked about being alone for Christmas and she invited me to come with her to her brothers house. I was hesitant, but was easily convinced to join her. After the services, we drove to her house, dropped my car off and then went to her brother’s place. It was a huge gathering. There was at least 50 people there. I spend most of the time hanging with Denise and there was definitely some flirting starting between us. At one time we were sitting on the couch and she place her hand on my leg and began to rub in up and down. I was so turned on by it, but it also seemed so innocent. I drove her home, since she had a few drinks. During the ride she put her hand again on my leg and told me that I needed to come in her house to see the photo we were talking about earlier.

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 went inside her house and she lead me upstairs where the photo was hanging. Our bodies leaned together looking at the photo. I told her her it was beautiful. She then asked what I thought about her. I said she looked amazingly sexy. She smiled and I leaned in to kiss her. We stood in her hallway making out, our hands exploring each others bodies. She then lead me my hand to her bedroom. We continued making out as we stripped each other. First it was our shirts, then her skirt and then my pants dropping to the floor. She then pushed me to sit on the edge of the bed and began sucking my cock. It was amazing watching her head bob up and down on my cock. Her green eyes looking up at me with that smile. I ran my hands thru her long red hair as I was loving every second of it. Then I decided it was her turn for some oral pleasure. I laid her down on the bed and had the pleasure of kissing her legs as I removed her boots and pantyhose. Then moving to her wetness. She moaned and told me how much she was enjoying the attention she was getting. She then told me she needed my cock in her to get off. We went thru several positions, including missionary, doggie, cowgirl and reverse cowgirl. Eventually we were back to doggie and finished inside of her. We both collapse on the bed. We talked about how pleasurable the sex was for both of us. She fell asleep in my arms and I was tired also and decided to sleep there. I was awakened to my cock getting stroked. When she saw I was awake, Denise climbed on top of me for some 69 fun. We teased each other orally until I saw the time and knew I had to get going to get ready for work. She told me I could fuck her quick to dump my load. We got in missionary and I began fucking her. She was very vocal and kept telling me to do it hard and quicker. I released my load in her again. As I got up to clean up and get dressed, she laid on the bed and played with her vibrator till she came again.

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? Its sad to say I dont feel guilty about cheating on my wife. I have done it too often. I was nervous that she might have called me at home, but she didn’t. I was on cloud 9 the rest of the day. Denise texted me a few times during the day telling how much she loved her present. When I got home from work, we talked on the phone and she told me she felt wrong for fucking a married man. I told her it was not her fault. Denise did start avoiding me for awhile. Then in late May, we had to do a project for the church together. We quickly got over the awkwardness and finished the project. As we were getting ready to leave, we hugged and eventually had sex on the desk in the multimedia office in the church, Soon after that Denise has left the church and stopped responding to my texts. I feel guilty for forcing her away from the church. She was a very good sexual partner

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), I was feeling lonely

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

How intoxicated was your partner? A little tipsy/high

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? I have a friend that I share cheating stories with and he was excited for me

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? A little bit

Why do you regret this hookup? I did enjoy working with her at the church and now she is gone

What was the BEST thing about this hookup? How sexually gratifying it was

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

All things considered, how NEGATIVE was this experience? A little 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 really enjoy casual sex. It can be more freeing that hooking up with the same person constantly

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