Alternate Sexual Realities

[SmokingFap]

One of my favorite ways to fantasize is to remember a situation I've been in and how I wish it WOULD have gone sexually. Sometimes the situation wasn't even sexual at the time, sometimes it was, but could have been even better. Describe a "crossroads" moment you've had, what actually happened, and how you wish it would have gone as an alternate reality. I have several examples to share. Hope everyone will do the same!

 

[mrdiscreetshh]

mine would involve contractors that we dealt with handling my wife while I watch and instruct! so many scenarios!

 

[SmokingFap]

I'll share one of mine. Been a long time since I shared it.

Okay. So. One night, my sister was visiting my mother and I from out of town. I lived with my disabled mother and cared for her. Not as much as I would have liked to, but that’s another story. So my sister and I went out and got drunk, catching up on everything and having a pretty good time. We ended up going back to Mom’s, who was in bed by then, and drinking some more. E, we’ll call her, was about 40 at the time, three years younger than me. She was cute, if not quite pretty, at least in my eyes.

Anyway, as we got drunker, I worked up the nerve to bring up the times when we’d been younger and we had played around together (her jerking me off). But I told her that I’d always felt terrible about taking advantage of her. She laughed it off and said it had never bothered her, and even back then, she'd thought it was fun. She even told me that she had masturbated to the memory several times over the years...

Having made my peace on that subject, I was lamenting about not having a sexual partner at the time. Now, my sister and I hadn't been close since we were kids. She was actually pretty much a brat, and I never had any sexual attraction to her growing up, although she was pretty cute.

But that night, I said the thing I missed most about having a girlfriend or wife was just... boobs. I missed seeing boobs in person! E took a big gulp of her cocktail, then lit a cigarette, laughed and said, "Well, here ya go, then." She raised her t-shirt, braless, and showed me her cute little B-cups. Little bee-sting nipples, pink, nickel-sized areola. Nothing special about them, but it had been so damn long...

I said, "You've actually got cute boobs." (She really did!) She smiled in appreciation and let me look at them for a little bit more as she smoked her cigarette, getting a kick out of my attention. After a minute or so, she moved closer to me on my mother's sofa. She leaned up towards my face and just started kissing me. Again, I had never had a sexual thought about her since we’d been kids. But I was drunk and horny, so I started kissing her back. We made out for a good ten minutes, although (unfortunately) we did keep our hands off each other, except around our necks.

We finally pulled away from each other, panting. “You’re a really good kisser,” she said, smiling drunkenly.

“You, too,” I panted.

We couldn’t help but start making out again. Eventually, we stopped. I think we both wanted to take the next step. But we both chickened out. After all, she was my sister, and she was married to boot. We ended up going to bed (separately) and didn’t talk about it again. The next day, hanging out with our mother, we acted like nothing had ever happened.

Now, I really wish I would have pressed the issue. I wish I had stripped her down and fucked the living daylights out of her. We both might have regretted it forever, but goddamn, it might have been worth it.

 

[Bbl87]

I kinda wish I would have lost my virginity to my ex that broke up with me because I wouldn't have sex. Well, I did eventually, haha, but would have done it about 3 years earlier had I done it then.

I think it (along with finding out I'm on the more endowed side) would have given me more confidence sexually and I would have had alot more varied experiences that I'll probably miss out on in my current situation.

 

[mrdiscreetshh]

I loved reading every word! So hot and sensual!
All I could think of was a quick 69 having visual of her sweet ass and pussy while your cock is planted deep in her throat... oh man !!!

 

[haventdonethat]

Years ago wife and I were very close with another couple. We did everything together.
Eventually, they started the long slide towards a divorce but not before he started fucking my wife with me.
One day I brought the other woman for a really good motorcycle ride,; lots of curved roads, shifting in the high revs for a vibrating seat, wind in our faces.
At a rest stop were smoking and having a drink we started talking about sex. She stated she fantasized about a threesome with me and wife. I was flabbergasted, didn’t know what to say, and just questioned what this would look like. She paused and said “I’ve always been fascinated by her breasts”..
Alas, it never happened.

In my alternate universe, we go on to have that threesome, then more combinations of all four of us.

As a bit of an aside, she contacted me through social media a while ago but nothing sexual was discussed. Yet.

 

[mrdiscreetshh]

Years ago wife and I were very close with another couple. We did everything together.
Eventually, they started the long slide towards a divorce but not before he started fucking my wife with me.
One day I brought the other woman for a really good motorcycle ride,; lots of curved roads, shifting in the high revs for a vibrating seat, wind in our faces.
At a rest stop were smoking and having a drink we started talking about sex. She stated she fantasized about a threesome with me and wife. I was flabbergasted, didn’t know what to say, and just questioned what this would look like. She paused and said “I’ve always been fascinated by her breasts”..
Alas, it never happened.

In my alternate universe, we go on to have that threesome, then more combinations of all four of us.

As a bit of an aside, she contacted me through social media a while ago but nothing sexual was discussed. Yet.

GO for it!!!!!! omg! eat her pussy so good

 

[SmokingFap]

Years ago wife and I were very close with another couple. We did everything together.
Eventually, they started the long slide towards a divorce but not before he started fucking my wife with me.
One day I brought the other woman for a really good motorcycle ride,; lots of curved roads, shifting in the high revs for a vibrating seat, wind in our faces.
At a rest stop were smoking and having a drink we started talking about sex. She stated she fantasized about a threesome with me and wife. I was flabbergasted, didn’t know what to say, and just questioned what this would look like. She paused and said “I’ve always been fascinated by her breasts”..
Alas, it never happened.

In my alternate universe, we go on to have that threesome, then more combinations of all four of us.

As a bit of an aside, she contacted me through social media a while ago but nothing sexual was discussed. Yet.

"So you're telling me there's a chance..." Lloyd Christmas, Dumb and Dumber

 

[sister jenny]

We were going to a party.
I had just dated my husband for a few months and he was visiting me in Sweden.
A friend of my sister was driving us there. We were all drunk and stoned.
My sister was up front and me and my future husband in the back. My sister starts stroking the driver, pulls out his cock and start giving him head.
My and future hubby just sit in the back and watch. She finishes and swallows his cum, and then act like nothing happened.

I really, really, really wish I would have been brave enough to start giving future hubby head at the same time. To share that moment with my sister and maybe it would have led to more stuff.
Maybe a foursome.
Maybe she would have sucked his cock too.

Afterwards no one said anything.
Sis has never brought it up.
Neither has hubby.
Or me.

 

[SmokingFap]

We were going to a party.
I had just dated my husband for a few months and he was visiting me in Sweden.
A friend of my sister was driving us there. We were all drunk and stoned.
My sister was up front and me and my future husband in the back. My sister starts stroking the driver, pulls out his cock and start giving him head.
My and future hubby just sit in the back and watch. She finishes and swallows his cum, and then act like nothing happened.

I really, really, really wish I would have been brave enough to start giving future hubby head at the same time. To share that moment with my sister and maybe it would have led to more stuff.
Maybe a foursome.
Maybe she would have sucked his cock too.

Afterwards no one said anything.
Sis has never brought it up.
Neither has hubby.
Or me.

Great story!

 

[sister jenny]

Great story!

Thank you!!

 

[SmokingFap]

Thank you!!

No, thank YOU! You made my cock ooze. In my jeans. In the library.

 

[SmokingFap]

so nice!!!!!!!

Do you have any examples you'd like to share?

 

[nightowl75]

I met my first lover when we worked at a restaurant when were in our early twenties. She was married to a guy who was about 48 and worked there. They lived near me, and I’d visit. She came onto me once when I was there and he was supposedly gone. I was shocked and naive. He set her up. I refused at first, but eventually started messing around with her. Months later, she came to my apartment and we had sex.

She insisted on it being natural, no condom, as she was on the pill. I was hesitant but thought I’d pull out at the last moment. Nope. It was so wonderful, so natural. We did it again, but after that I would (somehow) stop before the point of no return, just out of fear of pregnancy. In an alternate universe, I don’t hold back. Maybe she gets pregnant, and maybe not. The risk was well worth it.

Fast forward to several years later, and she ended up having a baby with his son who was visiting at the time. She’s never admitted it, but I believe it’s true. Not judging her, as she was told to do these things. It was complicated. The old man died a couple years later.

 

[SmokingFap]

I met my first lover when we worked at a restaurant when were in our early twenties. She was married to a guy who was about 48 and worked there. They lived near me, and I’d visit. She came onto me once when I was there and he was supposedly gone. I was shocked and naive. He set her up. I refused at first, but eventually started messing around with her. Months later, she came to my apartment and we had sex.

She insisted on it being natural, no condom, as she was on the pill. I was hesitant but thought I’d pull out at the last moment. Nope. It was so wonderful, so natural. We did it again, but after that I would (somehow) stop before the point of no return, just out of fear of pregnancy. In an alternate universe, I don’t hold back. Maybe she gets pregnant, and maybe not. The risk was well worth it.

Fast forward to several years later, and she ended up having a baby with his son who was visiting at the time. She’s never admitted it, but I believe it’s true. Not judging her, as she was told to do these things. It was complicated. The old man died a couple years later.

Holy shit! I'm suddenly having trouble breathing!

 

[cdstefi]

That time I probably should have lost my virginity.

I was at university, hanging out chilling with a friend who was a girl (not my girlfriend, my roommate's girlfriend) and we were listening to music (a Chic compilation FWIW) and sharing a joint and were very laid back. I did something daft like sticking a needle in my finger (don't recall how this happened) and Fay starts fussing over the blood, and she honest to God starts sucking my finger.

Now I was super uptight and while I liked her a hell of a lot, she was possessed of a really natural sexiness, it didn't even occur to me to take this as a sign or act on it. So there you go, just stayed friends with a woman who'd have taken my cherry and probably changed the course of my life.

 

[nightowl75]

It was all so much then. I was a shy, awkward virgin who had only kissed two girls before that, only because a classmate of mine felt for me and set up a double date situation and “truth-or-dare” game. I was afraid of getting the husband mad. He was a paranoid guy with many guns and yelled at people. And they lived on the third floor of the building.

He wrote a note to send with her saying I needed to have sex with her. NEVER was anything spoken about between the husband and me. It was like a game. He would leave the room and she would initiate sex if I was at their place. To be clear, as much as I could, I would make sure she was okay with it.

 

[Buttersctch]

There was one guy when I was in college that we should have just fucked and got it over with but we never did.

The first experience was a group of us was hanging out. I was dating at the time and he was not. A girl was there that was his ex, they had ended things mutually and were still friends. She was telling us about how he was quite gifted when it came to sexual talent and size. Of course we all started joking around about who could handle what size especially when it came to oral.

In an effort to have some fun and tease a bit we had a bag of those balloon they make animals out of and we started blowing them up and seeing who could fit how much into their mouth. Of course this got the guys attention and got them worked up. My boyfriend at the time came over and told me how we could practice the real thing later on. About five minutes after that this guy who we will call L came over and said if I ever wanted to see if I could handle him all I had to do was ask.

Now in an attempt to be a good girlfriend I went home with my boyfriend. In an alternate reality I would have went with L.

The second experience was a flip of the tables. L this time was dating and I was the single one. Our group of friends had gone to the mountains to spend the night, party, etc. During the day we had gone on a hike and found this great area of the creek that was deep and had a small spot to jump into. None of us had brought suits so skinny dipping it was.

I went up to the spot where people jumped from and prepared to jump. Several of the guys put their hands out to catch us and they were with all the women. I jumped in the direction of L and he sort of caught me. The way I landed with everything our bodies came together and he went inside of me and it felt amazing. We both kind of froze not knowing really what to do. In the end we broke apart as his girlfriend was there with us.

In an alternate reality we would have just started fucking or tucked away somewhere quick.

 

[soflabbwlvr]

During my undergraduate years I worked at a research facility on campus. My supervisor was a young female research professor who was attractive enough, but her supervisor was a smoking hot woman in her early 30s. She had black hair, a superb figure, was super intelligent, friendly, professional, and definitely the sexiest woman I had ever met up to that point of my life. I'll call her T. I worked there for four years, and during the entire period nothing sexual happened (except in my fantasies).

After graduation I had to move on, and the staff took me out to lunch for a small going away party on my last day. I returned to work after lunch, and found Ms. T sitting in my office, in my chair, with her shoes off and her feet on my desk. She told me to have a seat. My office mate's empty chair was the only other seat in our small office, so I sat down a feet from T. With her feet propped on my desk, her skirt slid halfway down her thighs, revealing several inches of nylon encased, very shapely legs above her knees. I couldn't stop staring. She always dressed stylishly professional -- never inappropriate, but not stiff or prudish, either --so I seldom glimpsed her legs above the knee. I was in heaven.

She talked to me about my time there, what I had learned, and how I would apply it to my future. We talked for about 30 minutes, during which she crossed and re-crossed her legs several times. I might not have been drooling, but I'm sure I had a stupid look on my face. Anyway, after about a half hour she stood up, congratulated me, gave me a hug and a quick kiss on the cheek, and then said her good bye to me.

In my alternate reality we did not spend 30 minutes talking. Instead, she locked the office door, opened her legs, and pushed my face into what I am sure was a very thick, dark bush. After I licked her to her satisfaction, she turned around, shook her ass at me, and told me to fuck her from behind. I can't even guess how many times I masturbated to this scenario over the ensuing years.

 

[HumpDayHoratio]

My best friend growing up had this girlfriend he worked with at a grocery store. She was cute as a button, curves in all the right places, small of stature and just ticked all the right things for him…and me.

We spent the whole summer together going to the beach, parities, riding together on the big bench seat of my ‘65 Galaxy 500, her nestled in between both of us, and just hanging out. We spent so much time together she sort of developed feelings for both of us I guess. Little looks, sitting a little to close to me, resting her heavy chest on my arm when riding in that car! All the little ”tells”….the problem? My friend was head over heels in love with her. It would have killed him, had I taken advantage.

At the end of that summer I went off to college and didn’t see them for a few months. I came home around Thanksgiving, and her parents had gone out of town, leaving her and her brother behind at the beach house. I got in town early before my friend got off work but went to the beach and she and I start drinking. She was giving me the puppy dog eyes, touching, and sitting close. I fell on my sword and honored my friend. Didn’t touch her. After a weekend of partying and fun I went back to school, they broke up shortly after as her parents moved back to another part of the state, and I never saw her again.

In my alternate reality, I take her on the kitchen table we were sitting at ravish her nubile body! My friend comes in and catches us and joins right in, a threesome of lovers who actually had feeling for each other...as we all three most certainly did.

The coda to this is the girl my friend did eventually marry, he tried to get a three way going once when they came up to see me a few years later at my apartment a couple hours away! I‘ve often thought…wrong girl, wrong time!

 

[AchtungNight]

I frequently imagine scenarios such as what you describe when creating my stories on Lit. I haven’t gotten nearly as much sex from real life as I’ve wanted and I never will, and I have a vivid imagination so… I’m also familiar with parallel universes in fiction so I’m creating one in my ficverse. My character Doug Ramsay is me in that universe. You are welcome to read my stories if you wish to explore their fantasy world.

To answer the post on topic, here’s one conversation in my life I wish had been more sexual-

[celebrity Alicia Witt smiles at me as I approach her VIP table after she gifted me a free VIP ticket to her concert in 2019. No other fans are in the way, unlike in the actual circumstances.]

Alicia- Hi. Did you enjoy the concert?

Me- Yes. Thx for the free ticket. I was not expecting it. I bought a ticket to a larger concert you were planning and got a refund when it was cancelled. I was surprised when you invited me to this free event by email form letter. Was that something you did for everyone who attended?

Alicia- Yes, but I only invited those who I believe are my most dedicated fans. I’m aware you are such, sir. You are the man who writes the Doug Ramsay stories, yes?

Me- [recovering quickly] Yes. You’ve read them? And seen the character based on you?

Alicia- Yes. You’ve had them online over a decade and they’re very good, please don’t be surprised. You are talking to the former star of Cecil B Demented. I admire your stories and wish to make a small change in our relationship. I think you need to better know me- to improve my character in your work if nothing else. Would you like to discuss the matter further in my suite upstairs, privately between us?

You can imagine how things might go from there, I hope. IRL, I know such a conversation will never happen, but I can dream.

 

[StrongMaster7]

Most of my alternate reality stories are just me not having the nerve to ask a woman for sex.

One of my best friends in high school told me his gf was really good in bed. They broke up and he moved away. I saw her at a party and she was friendly to me. I only wish I could have whispered to her how sexy she was and asked her to fuck.

In college I was a long time between girlfriends. One Sunday morning I was alone downstairs in the dorm lobby. The hottest girl in the dorm came downstairs in tiny white shorts and a tight white t-shirt and did some stretching right next to me as we made small talk. This girl was a dream with big tits, tight body, long blonde hair, and she fucked. I feel like if I had asked she would have given me at least a 'mercy fuck'. Of course, she would have also given me herpes and God-knows-what-other STDs. Might have been worth it.

 

[screwher]

In my alternate sexual reality, I handle the first time my wife cheated differently. I was furious and we were an eyelash from splitting. Shortly after though my wife’s tryst started to arouse me. But she went many years without so much as speaking to another man, outside family and work. But that night I would confess my desires about her having sex with our men and start our lifestyle that night. As opposed to many years later. Years we could have spent with her screwing numerous men!

 

[SmokingFap]

In my alternate sexual reality, I handle the first time my wife cheated differently. I was furious and we were an eyelash from splitting. Shortly after though my wife’s tryst started to arouse me. But she went many years without so much as speaking to another man, outside family and work. But that night I would confess my desires about her having sex with our men and start our lifestyle that night. As opposed to many years later. Years we could have spent with her screwing numerous men!

Better late than never, though, right? Eventually you lucked into a lifestyle that many men on here would envy.

 

[HumpDayHoratio]

Most of my alternate reality stories are just me not having the nerve to ask a woman for sex.

One of my best friends in high school told me his gf was really good in bed. They broke up and he moved away. I saw her at a party and she was friendly to me. I only wish I could have whispered to her how sexy she was and asked her to fuck.

In college I was a long time between girlfriends. One Sunday morning I was alone downstairs in the dorm lobby. The hottest girl in the dorm came downstairs in tiny white shorts and a tight white t-shirt and did some stretching right next to me as we made small talk. This girl was a dream with big tits, tight body, long blonde hair, and she fucked. I feel like if I had asked she would have given me at least a 'mercy fuck'. Of course, she would have also given me herpes and God-knows-what-other STDs. Might have been worth it.

I get it StrongMaster7! Sometimes though…

A colleague would always tell me when parting, “Drive Fast, Take chances!”, or as the old Smith’s song goes…”go out and catch something I’d be ashamed of!”

They got shots for them Crotch Critters nowadays anyway!