Role-Playing With A Friend

by Katie

What’s your gender? Woman
How old are you? 20
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Miami
Highest education received: Some college (currently in college)
What’s your occupation? student
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? free spirit
How many sexual partners have you had in your life (including oral sex)? >30

Role-Playing With A Friend

How long ago did this hookup happen? a week 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? He’s a former neighbor that I crossed paths with this past Easter Sunday, and I already posted our first hook-up. He’s in his mid-50s, has sexy blue eyes, an arrogant attitude, and is married but cheats often. His cock is above average, very thick AND well groomed ‘down there’, which is a PLUS! His wife stays pissed at him, and they rarely have sex, which is good for me. They fight often so he has an apartment that she’s unaware of. Since we started having sex, I’ve met him there a few times. Recently, he gave me a key, so I can crash to smoke pot. While I’m there, I tidy up the place. BTW: I’m a compulsive neat freak.

I hope this is not too lengthy and boring but I was hoping by adding more detail it would encourage other’s to try ‘role-playing’. I had fun, and everyone should try at least once!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day, we’d finished having sex and he told me his wife would never ‘role play’. I thought it was odd because I’ve dressed up for my ex-bf before, and it was fun. He asked if I’d like to. I’m always up for anything new, so I agreed. He wanted a ‘role-playing’ experience in which both partners assumed the role of a character and use improv acting throughout. He explained in detail, I got turned on, and we had sex again.

We discussed boundaries. I don’t like anything over the top and NO anal. Sorry, draw the line there. This was going to be his fantasy and his rules. I’d find out my character with a brief scenario minutes before and No Talking! At this point, the suspense was driving me crazy HOT.

He asked for my sizes to order an outfit, even heels. I offered to bring my own heels because I’m super picky AND I have a closet full. He insisted I’d like his taste. When everything was ready, we decided on a date and time.

I made plans to meet him after I dropped my dad off at work because my hair & make-up would be professionally done. Mom started ‘beauty day’ with me when I was around 8 years old so we’d look our best when dad leaves for work. I know it’s a silly tradition but I’ve continued by scheduling a hair styling, facial, manicure, and pedicure at the salon. Then, things get busy. On my way home, I’ll pick up dad’s suits, make his lunch, pack his bags, change into a super cute dress, drive him to the airport, walk with him to the terminal for my final hug and wait till his plane leaves. I normally don’t make plans on ‘drop off day’ because I’m on an emotional roller coaster and don’t want to be anyone’s ‘drama queen’ for the day. I was hoping the spontaneous acting would help clear my mind. Sorry to ramble.

I left the airport, picked up hot wings (for him) and fresh fruit (for me). Once inside the apartment, I noticed a brown shipping box and a dozen red roses in a vase on the counter. The roses had a card with the scenario. It’s my first day on the job, and this is the first time we meet. I’m an innocent French Maid that speaks no English. He’s a married, successful, and rich homeowner that seduces me. I was then instructed to send him a text when I was ready. My mind was going a thousand directions. It’d been years since I took French, so I found an app to quickly refresh while I dressed. I know the rule was no talking, but I thought he’d like to hear a few French words during sex. I was excited to get started but also a little nervous because I didn’t want to disappoint.

Inside the box was an XS maid costume with accessories and a pair of classic black & red bottom LV heels. I put on the stockings & garter. I’m short but this costume was VERY short, it barely covered my ass. I knew he’d love it. The panties were thin white lace thongs, poorly made, rough material & not comfortable! I tossed them in the trash cause’ they’d be the first thing off anyways. My hair was styled so I was careful with the head piece. The arm sleeves were rough and scratched. They got tossed with the panties. I put on the heels & looked in the mirror for final adjustments. I work hard to stay lean and firm and I’m not the type to brag but WOW! This looked HOT. It fit a little loose in the bust but there’s nothing I could do about that. LMAO. I remember thinking Beck would look sexier in this costume. We’re the same size and her tits would be busting out over the top. She doesn’t like hearing it but I think between the both of us, she’s the hottie.

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? I sent him a red lips & female devil emoji. He replied with a thumbs up emoji. I took the feather duster (with 3 white feathers lol) that came with the costume and acted like I was dusting something high. I heard the door open then shut. I felt chills down my spine as he approached me. His hand ran up the back of my leg and squeezed my ass. I turned around, acted surprised, and we kissed. Then, he sat me on the table, gently opened my legs and went down on me. I was already wet but his tongue motions made me cum more. He spent a long time eating me out; I had my first orgasm, and he licked up everything.
He unzipped his pants & pulled his cock through the zipper opening. I gave him a sloppy blowjob, then he sat me on the edge of the table again. He removed my shoes (I was still wearing the stockings), he placed my feet on his cock and I began giving him a foot job. He moaned with pleasure. He popped the garter clips with ease and began kissing my inner thigh while slowly removing the stockings. Glad I had fresh pedi. He started sucking my toes! OMG HOT! I felt chills & goose bumps while he sucked each toe and used his tongue to swirl between each one! WOW! I got caught in the moment and rubbed his face with my other foot. I was so wet it felt like I was sitting in a puddle of water. I thought he was ready to fuck but he pulled a bottle of warming pleasure oil from his pocket and placed my feet back on his cock. He poured oil on his cock and my feet so I gave him another foot job. My feet and toes are tiny and I tried my best to grip & stroke his slick cock. I could tell by his reaction this was a key part of his fantasy so I began using my toes and toe nails to gently rub against his hard cock. I felt him swelling & I thought he was going to cum.
I thought ‘maybe this is a foot fetish & no sex’.

FINALLY! He forcefully opened my legs! (I tried a little bad acting. Lol). I gave him puppy dog eyes that makes my dad cave into anything I want. I knew he was planning on ramming his dripping wet, slick cock inside me, BUT I was supposed to be “innocent.” So, I pretended to be a virgin. LOL I held his super slick cock at my wet entrance and rubbed the thick head up and down. I put one hand on his stomach to hold him back while holding his cock in the other. My body was craving rough/hard sex but I wanted to maintain my ‘innocent’ character. I kept saying, “Aie! Aie!” as the head entered. Then, I allowed him to enter SLOW & EASY. As he was going deeper, I winced like it slightly hurt and squirmed like I was in slight discomfort. When he was half-way, I made him pause then said, “Oui!” I kicked my legs as he slid easily all the way in then I gave a sigh of relief. I looked in his eyes as he began fucking me slowly. I had a surprise orgasm! (I went a little over board with the acting) LOL). Within seconds, he pulled out, stepped back and put my feet together and began cumming on them. I rubbed my feet together as he came. When he finished, my feet were dripping with sticky cum, and I rubbed his cock with my feet. He shoved his cock back in his pants, zipped up and walked out the door. I walked on my heels to the bathroom (obvious reasons) then checked my phone. I had a text from dad. He’d arrived with no problems. WHEW! Now I could relax.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? He came back and I was in the middle of wet swiffering to remove the cum off the floor, the ‘roll-play’ was over. I grabbed him a beer from the fridge and made myself a smoothie. He mentioned I could change clothes, but I told him I planned to take it off when we had sex again in a few minutes. He gave me an arrogant grin. I tossed his pants in the washing machine because they had lube all over them. He complimented my acting skills and said it went better than expected. He said he wasn’t expected the ‘virgin’ part. LMAO, I blushed when he said, “I’m glad we did this together. I know my wife would have NEVER performed as well as YOU!” I thanked him for the opportunity to help live out HIS fantasy.

We hung out for a few then went to his bedroom and had sex. He was able to last longer this time, and we both had orgasms.

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), Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more confident, To cheer myself up, I was feeling lonely, Didn’t want to disappoint my partner

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? My BFF Beck.
She thought it was hot and admitted it turned her on. She agreed lots of detail makes the story. She confessed her ‘roll play’ fantasy. WOW!

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? My first ‘roll-play’.
Getting my toes sucked.
Giving my first ‘foot job’.
Getting a dozen roses! Only a few guys have ever gotten me roses.
The Louis Vs! They’re the perfect accessory for any LBD.
The MANY orgasms! OMG!

What was the WORST thing about this hookup? I don’t want to call this “Worst” because I had so much fun!
Awkward moment: Running to the bathroom with cum on my feet. Standing in the bathtub removing the sticky cum and oil between my toes. LOL

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I enjoyed my first ‘roll playing’ experience. Everyone should have the opportunity to experience their sexual fantasy. If your partner/spouse is not willing, find someone you’re comfortable with. It should be done with an open mind and with a partner that wants YOU to enjoy YOUR fantasy.

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? I can’t believe his wife refused to ‘roll play’ with her HUSBAND! I was flattered & honored he asked ME.

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 type of ‘roll-playing’ should be done with an open mind and with a partner that want’s YOU to enjoy YOUR fantasy.

What do you think about the Casual Sex Project? I love this anonymous forum and enjoy reading other people’s experiences.

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