Sex With My Best Friend’s Sister – Part 3 [MF]

I’d been secretly hooking up with my best friend’s sister for a few weeks. Her name was Stephanie. It had started with a drunken kiss at a party, and three weeks later, we had a weekend-long bed session. She was wild and liked to try new things and liked how I took care of her and fulfilled her sexual fantasies.
A week after our weekend-long sex session, we had seen each other at a gallery opening, and she had given me a blowjob in the ally after the show. It was very open and public. Anyone could have caught us, and someone did.
But what surprised us was that the person who caught us was my best friend’s girlfriend, Victoria. What surprised us more is that she didn’t interrupt us and start shouting, make the situation awkward, embarrass me, or the girl who had my cock in her mouth. She didn’t move at all.
She had spotted us and had liked what she saw. As my best friend’s sister was sucking my dick, his girlfriend watched it and enjoyed it. I had noticed someone watching from the corner of my eye and slowly turned my head to see who it was. Our eyes locked, and I watched in delight as this gorgeous woman touched herself as she watched us.
She ran off as I finished, and Stephanie had seen her watching but didn’t have a problem with it. She rather enjoyed the experience.
I had seen Victoria later that night, and she had told me, “I won’t tell if you won’t.” as she looked at me seductively. This woman wanted Stephanie and me and didn’t seem to care she was in a relationship with my best friend.
It had been two weeks since that night, and I had been seeing Stephanie every few days, and we would hump like rabbits. Last week, she gave me a blowjob as I ate her out as we laid on the bed on our sides in a 69-type position.
Between sucks, she started asking me questions.
Her mouth made a pop sound as she pulled my dick out of her mouth and held it like a microphone.
“What’s the wildest sex thing you’ve ever done?”
I licked her clit for a few more seconds before I came up for air and answered. Keeping my fingers in her vagina.
“This is pretty wild,” I replied as I buried my face in her pussy. Her manicured pubic hair tickled my nose.
She giggled and let out a breath of delight as she started moving her hand up and down my shaft.
“I mean like really wild! Like porn-type stuff.” She said as she kissed the tip of my penis.
“Porn stuff could be anything,” I said as I moved my finger down past her vagina and started rubbing my finger around her asshole.
“Ohhh!” she exclaimed and went rigid for a second before she laughed and let herself relax.
She opened her legs wide to show me her cute little pink asshole. I continued to massage her clit as I slowly inserted my finger in her ass.
She took a sharp breath and exhaled slowly, and I felt her muscles relax, and my thumb slid deep in her vagina and my index finger deep in her asshole.
“Yes…” she whispered almost to herself. This wasn’t her first anal experience, but I think it was her most enjoyable so far.
She started moving her hips back and forth to control the depth my fingers went. She was in complete control of how fast and how deep, and she loved it.
She kept our conversation going as we continued to masturbate mutually.
“Blowing you in the ally was pretty wild!”
“Yeah, it was. I’ve never done anything in public like that before.”
“Me either.”
I paused, continuing to pleasure her as she pleasured me. Was now the time to bring up the fact that her brother’s girlfriend had caught us and she had enjoyed the show?
“I’ve never had more than one girl see my dick at the same time,” I said slowly. Looking to see how she would respond.
“I’ve never had someone watch me blow someone before.” She continued to jerk me off as she looked from my dick to lock eyes with me.
This girl had my dick in her hand. I had my thumb in her vagina and my finger in her asshole. We were past the point of being uncomfortable and judgementle. There wasn’t going to be much I could say that would cause a problem. And this girl was a freak and I wanted to see how freaky she could get.
“It was kinda hot,” I admitted as we kept eye contact.
She slowly smiled and looked away, with her cheeks going red as she thought of something.
She looked back at my penis as her hand continued to move up and down my shaft. She leaned over and began sucking again. Her head moved up and down, up and down, her eyes were closed tight. As if she was transported back to the moment in the ally way, imagining Victoria watching us.
Up and down, up and down. I was going to cum soon. Up and down, up and down, up and off as she paused her hand motion and looked back at me.
“It was really hot. I was really into it. And you were really into it. And she was really into it.” She said in rapid succession as an idea seemed to form in her head.
“Yeah, she was,” I added. Hoping this conversation was leading to what I hoped it would.
A beat. She was contemplating something.
“We should invite her over.” She said.
I pulled my fingers out of her.
“What? Now?” I asked.
“Yeah! Just see if she wants to come hang out. We can test the waters with her. See if she just likes watching…or if she would want to join.
“What about your brother?” I asked.
“Eww.” She replied.
“No, haha. I mean, it’s his girlfriend.”
“It’s her decision, and she seemed to have already made it when she decided to watch you cum on my face instead of walking away.”
“Yeah, but, I don’t know if I could do that to him, he’s my best friend.”
“Best friends aren’t meant to sleep with their best friend’s sisters either. Besides, she drunkenly told me a few months ago that they weren’t monogynous. So you’re in the clear.” She explained very convincingly.
“She told you that?” I asked, a little shocked at this news.
“Oh yeah, she told me right before she kissed me.” She said very nonchalantly.
“What?!” I snapped my head up to look at her. A big, confused look on my face.
“Haha, yeah. Like 30 minutes after we kissed.” She replied.
“She kissed you at the same party where we kissed the first time?” I asked.
“Yeah,” she responded casually. “She told me she had seen you and I kiss and wanted to try it out.”
“And you kissed her back?”
“I mean, it was like 2 seconds. People were still at the party. But after a drunken kiss and then watching us hook up while she touched herself. I’m pretty sure she’s down.” She replied.
This was blowing my mind. Could this be happening?
“Are you sure you wanna do this?” I asked genuinely.
“Do you want to?” she replied.
“I do,” I said
“Me too.” She said.
We smiled at each other. I stroked her vagina lips with my fingers. She was soaking wet. My dick was so hard and ready to have this girl—no more foreplay.
Our smiles turned to lust as we both leaned in and started making out. She pushed me down, so I was lying on my back. She sat up, flung her leg over my torso, and straddled me. She grabbed my dick with her left hand as she played with her clit with her right hand. She guided my penis up to her ass and lowered herself onto it. My dick slowly glided into her tight asshole as she let out a breath of pleasure.
“She could be even kinkier than me.” She said with a wink and a smile as she lifted herself on her knees and started moving up and down on my dick.
“I doubt that.“ I said with a smirk.
“We’ll see.” She replied with a wink.
She started grinding slowly but rapidly increased her pace as her asshole stretched out.
“Fuck!” We both screamed in unison. I had found her G spot in her ass and was hitting it hard. As she climaxed, I felt myself about to cum. I tapped the side of her leg twice to let her know I was close.
She hopped off and watched in enjoyment as I came all over my stomach. She leaned down and licked some off, and swallowed it with a smile.
She looked up and seductively.
“Okay,” I said between deep breaths. “Text her.”
Stephanie invited Victoria to come over to my house to hang on Friday as her boyfriend would be on a hunting trip.
Victoria agreed.
Friday night came. Stephanie and I had a lovely dinner and had just opened our second bottle of wine when we heard a knock at the front door.
We opened the door and came face to face with Victoria in a long peacoat.
I invited her inside and shut the door behind her.
PART FOUR IS COMING SOON.
This is part 3 of the series –
Read Part 1 Here –

[FM] Groped at a Party

I was at a party with friends from school. We had a small class and we still keep in touch every few months. A guy from my class was there and had been drinking before I could get there from work. As i sat on the couch with my drink, I messaged my boyfriend and let him know where I was.

I soon got a message from my the guy from my class who was sitting on the couch on the opposite side of the room from me. He started flirting with me and telling me he was imagining what my tits looked like. He was trying his hardest to get me to meet him in a room so he could touch them. I had been telling him no, but the attention had started to turn me on. I messaged my boyfriend and told him what was going in and to my surprise he said I should. He has always had a fantasy of showing off my tits to strangers and now there was an opportunity.

The best hate sex [FF]

Someone [requested](https://www.reddit.com/r/gonewildstories/comments/qmv3q1/request_anyone_had_a_real_hatefuck_experience_mf/) a hate sex story and I am more than happy to indulge. I still get fucking pissed when I think about this… and turned on. I’m pretty sure my keyboard is never going to recover because I just angry-typed this out.

I grew up in a very conservative place. When I was in college in 2010 most people in the area did not understand LGBTQ folks, so I kept my bisexuality pretty under wraps.

I was dating a girl who was very much out and hated that I stayed in the closet. She had a really accepting family and did not understand my hesitation. She thought it was like ripping a bandaid off and told me I was being dramatic.

I should probably also note she was really volatile and kind of a difficult person to date. We did not have the healthiest relationship, but god damn it was she was great in bed.

So I don’t want to get too much into the specifics on this, but basically this bitch outed me in a very public way. I still get made when I think about it.

[F] I used to be a simp girl for a very hot guy without realizing it ..

I’m not going into details … but I was still in freshman college .. and usually girls would get a lot of attention when it’s their first year in college ; but I didn’t because there was tons of better girls out there and I looked kinda manly … so I was a bit desperate for it, and I would try and chat with the guys online and get a connection because when I’m with them in real life there’s better girls around so online was just easier ..

I would usually just chat and so on , but like I would try to open up chats with even hot guys which I would usually get my requests ignored . Other than that 1 guy, he was a hottie . Very attractive, we spoke for a while but it turned very sexual quickly, I am usually very skeptical when it comes to online fun but he was very hot and I knew him so I was like okay.. but he wanted to chat with me on his onlyffans. Yes he had an account there and in order to talk there I had to make an account and subscribe to him. And I’m ashamed to admit it, but I did do it.. only because I didn’t wanna lose the only hot person who talked to me .. again I was desperate and dumb back then .

[MF] Foreplay With A Married Friend

I’m not the best at telling stories, but I’ll do my best. This is a true story and no real names will be given.

I’m a 43 male and my best friend is a married female and also 43. We went to high school together and have stayed in touch ever since. We always had an attraction toward each other, even after all these years. We have always wanted to fool around, but either I was taken or vise versa.

I have always wanted to finger her, eat her out, and play with her ass. I’ll admit I’m very much into assplay.

Since we’ve been friends for so many years we talk about everything. Well one day sex came up and she asked me what my fantasy was. I told her I’d love to meet her at a park, finger fuck her till she cums, eat her pussy till she cums on my face, and finger fuck her pussy and ass at the sametime till she screamed my name.

To my surprise, she said I’ve always wanted to suck your dick till you drop your load down my throat and swallow every drop.

She is being questioned by her sister [FF]

This is the continuation of the “She talked to her sister after I left” confession which I have posted earlier. After that incident things were normal and she wanted to see me desperately again over the dinner. So she talked to her sister that we are planning for dinner again and if it is fine with you after whatever happened. Her sister said it’s absolutely fine and also joked about, “I’m also fine with what you both are into….haha….and it’s ok if you don’t lock the door again”. Hearing such response, she felt offended but dirty at the same time. She said ok.

After sometime her sister said “I want to ask few things if you are good with that”. She said “Yes please”.

(Her) from how long you both are into this?

(She) why are you asking such questions?

(Her sister) Simply, I just want to know.

(She) from couple of months

(Her sister) Oh really! Looks like you love it and enjoy a lot. I heard and saw that day

(She) Hmmm (Offended)

(Her sister) how does it feel like being with a same gender?

I [M] Filmed an OF Scene with an escort [F] con’t

[First Part](https://www.reddit.com/r/gonewildstories/comments/qdh6v7/filming_of_content_with_an_escort_mf_part_1/)

When I saw that Aimee (not her real name) was traveling through DC again I reached out over email and we arranged the details of the date. I had a special request and Aimee loves a good role play, so she said she was game and would really get into it for me.

On the morning of our appointment I met Aimee at her suite. As usual she looked like a total knockout in a white blouse, tight pencil skirt, stockings and Louboutin heels. If you ignored her bedroom eyes, plump DSLs, and huge DDDs trying to burst out of her blouse she would look just like any other young hot business woman in DC. We spent some time catching up on the couch in the sitting room and reviewing the boundaries of the scene before I excused myself to grab a quick shower. I came out wrapped in a towel and Aimee handed me her phone and said, “Here you go Mr Photographer, tell me what you want me to do.”

Favorite Quickies Part 1 [MF]

I am sure for all of us we have certain memories that come to mind whenever a specific phrase, location, season or even an action presents itself. Certainly, in this world of COVID and the isolation that occurred for part of the year, it seemed that the quickie, especially car sex, seemed to move front and center in the dating/hooking up world. I have read/heard many a story about different adventures. In my own personal world, I have always had a special appreciation, borderline fascination, with quickies. Not so much the ones where my girlfriend/wife and I are exhausted, climbing into bed at night and the quickie is a good compromise for that current time and place. It’s really the moment where your passion, want and desire for someone becomes all-consuming and that feeling is reciprocated by the other person. When those moments occur in a setting in the public world, it almost always leads to a great memory that can stay with each of us for life.

at the movies [MF]

this week, I finally got to go out with a guy I’d been sexting for over a year… he is in an open relationship and our interest in eachother has always been mostly sexual, though he’s also a good guy. we’re both quite busy and have been trying to meet at eachother’s houses for a while now, but never managed for a number of reasons. I’d been to a movie with him, before the pandemic, and it made me really hot the way he played with my thighs during the film. yesterday, we did that again.

only this time, we were nearly alone at the movie theater: only two separate people were there as well, and sitting closer to the screen in a way they couldn’t see us. we both knew something would happen… I wore a skirt on purpose. but we couldn’t even kiss, as it was a policy at the movie theater to keep your masks on during the movie.

[35m] [43f] first time together [mf]

Something I hope happens soon

(35m (43f) I have been talking with this gorgeous woman for a few weeks and we are going to be getting together IRL.
I am allowed to do anything I want except cum on her face (I wouldn’t want to cum on her beautiful face anyways, ok maybe a little) this is my fantasy of what will happen!