Unexpected sex

[soflabbwlvr]

Except for sex between married or committed couples, most sexual activities occur as a result of careful planning or intense effort. But what about those times when you just get lucky? Let's talk about those times when you weren't planning anything, when you were just minding your own business with no expectations whatsoever, and then WHAM! Seemingly out of nowhere, there it is.

I'll start.

Several years ago I was driving home from work when I got a little impatient with the parking lot otherwise known as I-95. I jumped off and took side streets, even though that sent me through some questionable neighborhoods. I was caught at a traffic light between a used car dealership and a seedy motel when a young black woman ran up to my car and started pounding on the passenger side window. I ignored her at first, but it was a rather long light and she wouldn't leave. I rolled down the window, and she frantically asked me for a ride. She was cute and looked harmless, so I told her to get in.

As we drove off she explained that she was with a trick at the motel when the guy just started going crazy. She was afraid for her life, so she took off running. I wasn't aware that was an area frequented by prostitutes, but she was wearing tiny shorts and a small tight shirt, so I guessed her story could have been true. I drove her about 20 blocks until I reached the point where I needed to turn and travel east. There was a McDonald's at that corner, so she asked me to buy her something to eat. I did, and then she asked me to pull into the alley behind the McDonald's. I thought she wanted to eat in the air conditioning, but she started taking off her shorts. She said she wanted to thank me, but didn't have any money since she took off before the guy could pay her. I told her I didn't have a condom, so she leaned over the console, opened my pants, and blew me. The girl was good. I usually require about 30 minutes to come from a blow job, but she did it in 10. When I was done, she jumped out of the car, took her bag and soda, and disappeared into the night. I got back on the expressway and drove home, one load lighter.

 

[StrongMaster7]

One of my male friends had a gf who went to the college I went to. He gave me the go-ahead to try to screw her. He had apparently talked me up to her as well.

One afternoon, I dropped by her dorm, a large all-girl high-rise. She was in a leotard doing ballet stretching exercises. Now this gal was tall, maybe 5' 9" and maybe 135 or better. She had a great shape with long legs, narrow waist and very big tits. She was obviously showing off her body to me as we chatted. She never stopped bending over and doing her stretching routine. Maybe I read it wrong, but her words didn't match the physical messages I was getting. I half-heartedly mentioned our dorm cocktail party later that evening and she said she was already going to a "wacky hat" party. End of story, I thought.

Later that night I was drinking heavily at our dorm cocktail party when she showed up in her wacky hat and leotard! I offered her a drink and she said yes. I asked if she wanted to get high and she said yes. I got the feeling that she was just going to keep saying yes.

Up in my dorm room, I worked my hands into that leotard and freed one of those big tits. She wriggled out of the tight-fitting garment and I was all over her. I'd like to say I gave her the best fuck of her life, but those tits were just too much for me and I didn't last long. I got her a few more times over the next few years.

It was such a surprise to see her show up at the party and even better that she was ready to play!

 

[ToysAreUs]

This brings back two great memories. I was at a Car Convention about 20 years ago and after a morning event I decided to take a soak in the Motel's hot tub before lunch. When I walked into the room there was a lady-acquaintance in the tub alone.

She was beautiful, about five years older than me (41 or 42) 5'8, 140 pounds and had a Louisiana accent that was as smooth as her skin. We soaked and talked for about 45 minutes and by that time we were both getting hungry so we went back to our seperate rooms to shower and dress before eating.

I walked to her room to collect her to go to lunch, but she had other plans. She opened the door in her bath towel and pulled my inside her room and dropped her towel on the floor. She had ordered four Bloody Mary's that were sitting on one of the night stands waiting for us. We undressed me (LOL) and we spent over an hour orally pleasing each other. She warned me that when she 'came' she might loose some control and holy orgasm, Batman ... she beat and slapped my back, squirmed and wrapped her legs around me so tightly I could hardly breathe. Bloody Mary time.

We spent the next hour making mad passionate love and in the middle of it, the Motel Staff (or fire department) decided to have a Fire Drill and the alarm horn was located right outside her room. Not wanting to be seen together by others attending the Convention we were in a bit of a fix, so we went back to screwing each others brains out. Eventually we were both exhausted so we drank our second Bloody Marys but by that time the ice had melted.

We took a shower together and I discovered her breasts were hard-wired to her clit, so I just had to make her cum one more time in the shower. The following morning we met to go to breakfast and I received one of the best blow jobs I have ever had. We dated off and on for about a year, but her teen son ran as much interference as possible which made everything awkward. Shame.

A second great memory happened next door to me. The couple that lived there took a European vacation for three weeks during the summer. Their sister-in-law came to town to house sit and feed their cats. We had known each other very casually over ten years. She was also a couple years older than I was, about 45, 5'4", 135 pounds and she had enormous breasts.

One evening there was a knock on my door and she asked me to change a light bulb for her. This made sense because the house was built in the late 1800s and has 9' tall ceilings. The burned out bulb was (you guessed) in the master bedroom. I was just able to reach the lamp while standing on the bed and after I changed it, she offered me a glass of wine.

We sat in the 'great room' and polished off the bottle and started a second one while sitting in the dark, watching the view. Out of blue, she grabbed me, kissed and started to fondle me. In a couple minutes we were back in the bedroom.

She was also a fantastic lover and rather open-minded. Her sister-in-law had left her dildo sitting like a trophy on top of the dresser (yes, I noticed it when I changed the bulb) and she said since they were sisters it must have been left there for her to use. So, we did. We stayed up until after 3 AM alternately making love and drinking wine.

My (same) neighbors vacation about every other year and my friend still comes to town to house sit, so she has been a long-term lover. I hope the neighbors go on vacation this summer.

 

[JamieGirl0519]

I love these stories!!

Heck, alot of the sex I have had has been "unexpected", not planned what so ever!!!!!

 

[opti1]

Surprised this thread hasn't had more traffic. I would imagine that the most 'surprising' sex is when the guy didn't think it would happen and was instead initiated by the woman.

In college there was a woman I went to HS with. Didn't know her well in HS, but a little. She went to the same college as I, but dated a friend of mine. She called one day, long after they had broken up, and asked if she could come by.

Awesome tour of the house, concluded with awesome tour of her body. She totally used me while in town (she had transferred by then) and I totally couldn't have cared less. What a great afternoon.

 

[whynotjustsayit]

Surprised this thread hasn't had more traffic. I would imagine that the most 'surprising' sex is when the guy didn't think it would happen and was instead initiated by the woman.

In college there was a woman I went to HS with. Didn't know her well in HS, but a little. She went to the same college as I, but dated a friend of mine. She called one day, long after they had broken up, and asked if she could come by.

Awesome tour of the house, concluded with awesome tour of her body. She totally used me while in town (she had transferred by then) and I totally couldn't have cared less. What a great afternoon.

Very cool story, opti1.

 

[englishgent73]

Surprised this thread hasn't had more traffic. I would imagine that the most 'surprising' sex is when the guy didn't think it would happen and was instead initiated by the woman.

In college there was a woman I went to HS with. Didn't know her well in HS, but a little. She went to the same college as I, but dated a friend of mine. She called one day, long after they had broken up, and asked if she could come by.

Awesome tour of the house, concluded with awesome tour of her body. She totally used me while in town (she had transferred by then) and I totally couldn't have cared less. What a great afternoon.

Great story! I love it when it's not me initiating anything, even better when it happens out of the blue.

 

[DarkPleasures]

Just last Tuesday I was on vacation with the family. I was outside when the construction worker from next door came out to smoke. We started talking and we just started kissing and we went in his room where his roommate was he started taking off my cloths and next thing I new i was sucking a cock and getting it from behind. They had some huge cocks. Only problem was they couldn't move with the same motion as my husband so they couldn't give me an orgasm..

You keep telling nearly the same story in different threads, but key details are messed up. (Like the construction man at YOUR house, not on vacation. Or different men you fucked "just recently on vacations", but it wasn't last Tuesday.

 

[john_johnson]

When I was younger my cousin and his girlfriend came to my house to go swimming. When we all got out of the pool my cousin asked his girlfriend to fuck the both of us. I was a little surprised but would have done it but she was too nervous, she didn’t want to disappoint him so she gave me a handjob while he ate her out. A real surprise to both of and a pretty fun time.

 

[simpletimes]

You keep telling nearly the same story in different threads, but key details are messed up. (Like the construction man at YOUR house, not on vacation. Or different men you fucked "just recently on vacations", but it wasn't last Tuesday.

Such is the problem when some dude tries to portray himself as a sexy lady, the boys do not have the proper words to describe how a woman really feels. Most times it is easy to spot the impostors or trolls.

 

[DarkPleasures]

Such is the problem when some dude tries to portray himself as a sexy lady, the boys do not have the proper words to describe how a woman really feels. Most times it is easy to spot the impostors or trolls.

Yeah, this one was obvious from its first post. (Now in How To, titled Cheating.)

 

[simpletimes]

Yeah, this one was obvious from its first post. (Now in How To, titled Cheating.)

Must be because it's summer time and all the boys are out of school and bored.
Then there are those who feel it necessary to make a couple accounts. Ah the joys of the internet and obscurity.
At least I don 't have to worry about getting the rancid PMs like you poor ladies.

 

[HornyVikingMN]

Outdoors, Public and Unexpected all at Once

I think I have posted this story somewhere else on Lit, but it fits here, too.

In college, my ex gf and I were at the same outdoor concert at another college. The breakup was fresh, and I was kind of being an ass about it. We were hanging out in the same large group that day and I'm sure all the beers I drank didn't help me be nicer to her.

Eventually, she had enough and came up and grabbed me by the arm and started walking me away from the crowd. She sat me down and we had a very good conversation and pretty much cleared the air between us. I apologized for being a jerk, and she told me that she was glad because she didn't want our relationship to end on such a bad note.

I thought we were done and going back to join the group. Instead, she jumped up, pushed me over and then turned and ran toward a woodsy area even further from the stage and the crowd. I may be an ass, but I'm no dummy, so I got up and chased her to the woods. After we passed a few other couples doing it in the tall grass she stopped, turned to face me and started to undo her pants. She dropped to the ground, pulled her pants down and motioned for me to join her.

With the music and noise of the crowd in the background, the sex was awesome and we both have a great memory that we still talk about whenever we see each other.

 

[saguarospines]

I'm also a little surprised this hasn't gotten many responses.

A couple of years ago I did some traveling by myself for the first time. I ended up going out to the desert and staying at a hostel in Arizona. While I was there I was pretty shy, but this man from Australia took interest in talking with me. He was probably in his late 20s - early 30s. Blond. Huge arms. I told him I was going out to the desert to walk around on some trails the next day, and since I had a car and he didn't, he sort of invited himself along. The next morning he showed up at the car as promised.

We did a lot of sight-seeing and touristy stuff. We got along fairly well. There were a couple of instances throughout the day where he would touch my waist or my hair or my arms and I would think "Huh. That was weird." There was definitely a weird energy that started building, but for the most part I just ignored it, thinking I was too young for him or not his type or something. Somehow in my head this was totally platonic, so I was absolutely blindsided when we walked back to the hostel after getting a few drinks that evening. We were sitting on the front porch of the hostel with everyone else. At one point everyone but us decided to turn in for the night and he immediately seized that moment to start kissing me. For whatever reason this totally caught me off guard but I enjoyed it... so when he asked me if I wanted to go somewhere more private, I said yes and led him to the back of the hostel. I spent a lot of time being pressed against that back wall and pleasuring and being pleasured. It was really hot and totally unexpected (at least for me).

 

[opti1]

I'm also a little surprised this hasn't gotten many responses.

A couple of years ago I did some traveling by myself for the first time. I ended up going out to the desert and staying at a hostel in Arizona. While I was there I was pretty shy, but this man from Australia took interest in talking with me. He was probably in his late 20s - early 30s. Blond. Huge arms. I told him I was going out to the desert to walk around on some trails the next day, and since I had a car and he didn't, he sort of invited himself along. The next morning he showed up at the car as promised.

We did a lot of sight-seeing and touristy stuff. We got along fairly well. There were a couple of instances throughout the day where he would touch my waist or my hair or my arms and I would think "Huh. That was weird." There was definitely a weird energy that started building, but for the most part I just ignored it, thinking I was too young for him or not his type or something. Somehow in my head this was totally platonic, so I was absolutely blindsided when we walked back to the hostel after getting a few drinks that evening. We were sitting on the front porch of the hostel with everyone else. At one point everyone but us decided to turn in for the night and he immediately seized that moment to start kissing me. For whatever reason this totally caught me off guard but I enjoyed it... so when he asked me if I wanted to go somewhere more private, I said yes and led him to the back of the hostel. I spent a lot of time being pressed against that back wall and pleasuring and being pleasured. It was really hot and totally unexpected (at least for me).

Nice. Thank you for sharing. You, too, Viking.

 

[DarkPleasures]

Must be because it's summer time and all the boys are out of school and bored.
Then there are those who feel it necessary to make a couple accounts. Ah the joys of the internet and obscurity.
At least I don 't have to worry about getting the rancid PMs like you poor ladies.

Quite true.

 

[DarkPleasures]

At any rate, I reread the cheating thread and see you did speak of construction workers while on vacation though the "yesterday" (as you wrote it) wouldn't have been a Tuesday. No worries though. I apologize for getting that detail wrong.

 

[tornandfrayed]

I'd like to offer a story here and I can assure you it is 100% true, aleit quite a while ago since it took place.

I was at a college in the North Of England and had enrolled on fine arts course, one of the tutors was a woman in her early 50's, she was very slim with long bron hair way down her back, from behind she easily passed for mid 30's and it was only the lines on her face which betrayed her true years. I was 19 at the time and like many young males at college enjoying the excitment of casual sexual encounters with girls of my own age range. I'll re-name the tutor, although by now she will have retired, but it seems unfair to use her real name, so I;ll go with Ms Parker.

For the first autumn term I had a class with her once a week on a thursday morning and I used to look forward to sitting watching her move around the room with her long hair swishing from side to side and her perfect little bum in the those tight leggings which she always seemed to favour over skirts or dresses. I was very attracted to her but as far as I was concerned she was out of bounds a) because she was a tutor and b) becuase of the age gap and c) beciase she showed no interest in any of the young males students.

I rarely spoke with her other than to clarify instructions on the work we were doing and in fact I was scared to death of speaking to her as she had such a posh accent. Perfect English, no regional slant - I guessed she had come through a very wealthy publc school and from a well to do family.

I fantasised about her reguarly and wondered what it would be like to fuck such a classy woman and these thoughts got me through some long nights and I admit thinking about her whilt fucking other girls.

It wasnt until the end of the year show and I was helping to put together an exhibition at the local arts centre with 4 other students when it happened. We finished quite late and she offered to drop us all off at home in her car. As we drove round the winding country lanes of West Yorkshire I was thinking about anything other than her...in a way I'd moved on with my fantasies and she was off the radar. Me and one other student were last to be dropped off and I offered to get out with him to save her a few miles. She insisted on taking me all the way as it was raining. As she drove down the lane to where I lived she pulled off down a small b road and stopped the car. In short she asked if I thought she was attractive. I can still remember the feeling of excitement and terror and the rushing of blood both in my cock and brain. I really was scared to death. She leaned over and we began kissing, it was amazing she smelt great, she tasted even better and it seemed to go on forever. I felt her fingers undoing my jeans and the coolness of her fingers as she slid them over my swollen cock, all the time she kept on kissing more forcefully and deeper. She slowly wanked (jerked) me off, and I exploded in her fingers. I don't think I lasted longer than 5 mins. She gave me tissues to clean up and drove me home. Nothing further was said about what had happened. Looking back now, I can't beleive why I didnt at least undress her or touch her breasts or rub her pussy - it was unexpected, highly erotic and for me a missed opportunity i still think about 20 years later.

 

[DarkPleasures]

HaHa no sorry i'm all woman don't be mad you cant get some. I like how people are so jealous they will try anything to dispute what you wrote how pathetic.

I doubt anyone is jealous of AIDS and loose morals. Funny how that's your go-to phrase and how you think cheating on someone you made a commitment to is "no worse" than a single person having sex.

Go away now, troll.

 

[AlwaysDancing]

This is a good topic however genuinely it was started.

I'm surprised I have never had unexpected sex. My significant others have surprised me, sure ... But I don't think that was the intent of the post. I have had sex that wasn't planned, but if I'm honest, I passive aggressively put myself in those spots. The times when I could have had truly unexpected sex, I extracted myself from those predicaments ... For better or worse.

I did surprise a gal ...

Working at a 24 hour drive thru on the grave shift (the lobby was closed) a gal point blank said she'd get naughty with me if there ever was a chance. I casually went to the other crew person and said, "hey, its slow, why don't you call it a night.".

Her eyes went saucer wide as she confessed she didn't even consider I could/would do that.

We didn't have condoms and didn't fuck that time ... But we did play around a bit. I guess that's ny closest story.

 

[Afterhours22]

One experience comes to mind...

A friend and I were hanging out drinking a few beers when he got a call from some girl he was banging on a frequent basis. She wanted him to come over but he told her that him and I were hanging out. She told him to bring me over, too.

He got off the phone and looked at me and said, "Maybe she wants to have both of us." I just laughed and went along.

After getting to her house, I found out why she wanted me to come along. A girlfriend of hers was staying and thought she needed some company, too. Her friend's name was Margie and I was immediately taken by her ice crystal blue eyes. She was about 5' if even, kind of plump around the middle but very pretty.
My friend, Tom and his girl, Debbie, went into her bedroom, and Margie and I just sat there on the couch and got acquainted.

After a very short time, while we were talking, we heard Tom and Debbie having sex. Margie and I just looked at each other and started laughing. She told me that she wasn't usually this forward with a guy but wanted to kiss me. I wasn't going to say no, hell no! We started kissing and gradually got more passionate... our hands were roaming over each other and we both began breathing pretty heavy... her hand found my very hard cock outside my jeans. She then unzipped me and pushed her hand inside and wrapped it around my erection. I groaned into her mouth and slid my hand down into her shorts, found the edge of her silky panties and moved under to touch her hot and hairy pussy... both of us were in a fit of passion at this point... she broke away from my kiss and said, "Please don't think bad of me, I'm not normally like this at all...." I just smiled at her and we continued making out...
She pulled at my pants to get them off... I obliged by removing them while she got undressed..... she then pulled me on top of her, grabbed my cock, aimed at the entrance to her very wet pussy.... and I drove deep inside her in one stroke.... we made love slowly and passionately for several minutes before she cried out with her first orgasm... we changed positions and she began to ride me, grinding her pussy hard against my pelvis as my cock found her deepest depths... I knew I wasn't going to last long at this point... my cum started boiling up... I didn't have a condom on and told her that I was about to cum.... she was going at a maddening pace and just said, "Cum in me!" "I want your cum in me!" I began to cum very hard and she matched me... I thought we were going to break the couch... after coming down from our orgasms, we just laid there, her still on top of me, kissing me softly on my neck and lips... that was the beginning of a very hot friendship with Margie...

 

[whynotjustsayit]

NICE share, Afterhours22. WHEW !

 

[Afterhours22]

Thanks!

NICE share, Afterhours22. WHEW !

She was a lot of fun, then and many times after that....

 

[chatman2]

chatman2

Well I will add one..Love true happenings and reminds me of my past which I miss.
I was friends with a couple and we had decided to raise a couple of hogs together and take turns feeding.
His wife had told me when she went with me once to visit my wife in the hospital about it was her turn to have an affair as he had one which she found out about. Nothing happened as being friends etc I never took the hint.
One day when I was taking my turn feeding, she came down to the barn and told me she was ready and willing. She got up to me looking me in the eyes and I told her I couldn't do it to her as I was his friend also. She said she had to have a few drinks to get up the courage and guess she made a fool of herself. Her disappointment etc finally got the best of me so after kissing we go up to the hay loft and she dropped her shorts and we fucked standing up and neither of us lasted but a few minutes. I could see our houses thru the cracks in the boards so we wouldn't get caught. My wife said she heard her children calling for her once and she never answered and guessed she was at barn with me. I don't recall what I said but she was wondering what went on.
Well that started many a meeting in the woods, car, coming to my office after I closed for the day and what ruined it was he told her one day that she can do what she wants with me and he would play around as well.
I was leaving the office one night and their car pulled up and she got out. I asked her what was going on and she told me. I told her she fell for it and would cause trouble. I took her back home (they had moved to town within a mile of my office) in a few minutes and after that he kept her from me.
He had once told me if he ever caught her having an affair he would take her and her bags to the person's house and let her out. I lived in fear after that as it could happen. He liked my wife so didn't want to hurt her and all the time was having an affair and later married a co-worker at his job.
She was my first oral and also the woman that encouraged my wife to suck me. I think she taught my wife alot and I really miss our times we had.
My wife never knew for sure about us but had thoughts. This was the second time the spouse found out about me and their wife.

 

[whynotjustsayit]

Good share, chatman2.