Your sexual story, a chapter at a time

[lit_ch3]

I've hoped for an accidental meet, but that's not going to happen for variety of reasons.

Tempted? Thought about it? More times than I should have. But I respect her too much, so I swallow all that.

In the end I'm happy with the mutual "I've got your back no matter what" relationship we have. It's a comfort I offered to her first, and I felt good doing it. Getting it right back was icing on the cake.

 

[geronimo_appleby]

My story. Stared dating Lynn when we*** and felt her boobs. At 1*** began getting her naked and fingeriing her to orgasm. Age 22 had sex with her on our weeding night, my first time having sex. Next 40+ years, sex with Lynn. Her story has a lot more chapters and characters.

please edit your post and cut the underage references. under 18 isn't tolerated on Lit. you'll cause all sorts of problems with this.

 

[geronimo_appleby]

This is Lynn. Here’s my story in brief. If you want more detail, send me a message.

Lost my virginity as a **** after losing at strip poker.

Started dating Gary at *** and had my little boobs felt.

At ***, Gary got me naked and fingered me until I had orgasms. I kept my panties on.

We went steady until my senior year when he left for college and I could date others. A couple of them got my bra off and a couple fingered me.

In college Gary was still the love of my life, but I dated others for two and a half years. My freshman year, I was introduced to rum and Coke, which made my clothes fall off and my legs spread. I had sex with a number of guys, some for several weeks before I dumped them. My panties stayed on, even during sex.

Junior yers: Agreed not to date anybody else. Still being fingered by Gary. Senior year, got engaged and married after graduation.

Wedding night: Pantie finally came off and I took Gary’s virginity. Had sex seven times that night.

Had sex only with Gary until our 30’s when we decided I could have sex with others.

Had sex with men I met aat work and one old friend: 3 guys in their 20’s for whom I was the older woman; college friend; doctor from another country who was 65 and very good.

Turned 40 and have not had sex with anyone but Gary since then.

more underage references. please edit the post.

 

[Mike130]

Diane T, Connecticut/Boston, early 1970’s

Pretty girl, long brown hair, big eyes, very high forehead, like the girl who played Daisy Duke in the TV series, Catherine Bach. Dated while she was in high school a bit, then lost touch when I went to college. We never did anything while we dated, I didn’t even feel her up. What I do remember was that her divorced mother was a smoking hot MILF, wavy blonde hair, nice body. Was the only girl I ever dated that I wanted to do the mother more than the daughter.

Anyways, fast forward a couple of years, I was in college and she contacted me out of the blue and wanted to come visit. She had recently gotten engaged and the only thing I could think of was that she didn’t want to get married as a virgin. Or maybe she wanted to reward me for being a gentleman while we were dating.

Whatever the reason, when I got her into bed I came almost instantly. Maybe because of the anticipation I don’t know, but it was probably my most embarrassing performance. What I do remember is that she had a great ass and very long nipples.

I guess she got married, never saw her again, and lost track of her. Sometimes you just strike out…

 

[sftopbottom]

It was 1987 and I was fresh out of the Army, back home at Mom's, and looking for work.

A local housepainter was hiring. It turned out that the owner was the father of Connie, my younger cousin's best friend.

I had flirted and chased that girl all throughout my youth. She became a friend but nothing more. Boy, had she loved to tease me, though!

I took the job and guess who worked in her daddy's office? Connie snd I became fast friends again, catching up quickly on my first day.

On day two, She asked me to stay late and help organize the equipment storage area. The other guys elbowed me in the ribs and said, "Organize the equipment room" using air quotes. I laughed it off.

Later that night, work done and orgasms had, as we both got dressed in the storage room she said, "That was some good fuckin' but don't get attached. This won't happen again."

I was confused. "I fuck every guy my dad hires. It's a fetish. I don't even care what they look like. I just have to fuck 'em."

I worked for her dad for a few months after that, waiting for my Coast Guard application to be approved. I never saw her once I left town and always wondered what happened to her.

 

[gtnlynn]

This is Lynn with my sexual story:

Chapter one contains underage material.

Chapter two: Dating in high school with no sex. Gary promised me that he would not have sex with me until our wedding night because he loved me too much to risk getting me pregnant.

Chapter three: College. I only saw Gary once or twice a month and was free to date others. My dates discovered that two rum and Cokes made my inhibitions vanish, my clothes fall off, and my legs spread. I had lots of sex until the middle of my junior year when Gary and I decided I would not date anyone else.

Chapter three: Marriage. I took Gary’s virginity on our wedding night and we fucked seven times. Sex only with him until mid-30’s.

Chapter four: Mid-to late 30’s. Gary asked if I wanted to have sex with some of the men who were constantly after me I decided to try it, with certain conditions. I had sex with four younger men, one old college friend, and a 65-year old Russian doctor. When I turned 40, I stopped being with other men.

Chapter five: Just Gary and me. That says it all.

 

[Justfantasies]

Have you ever thought about writing a story of your sexual past? Maybe there are partners in your past that you’ve had a sexual or deeply emotional connection that you really can’t share with your current partner, but you remember fondly. Maybe Literotica is the place you can reminisce.

For older members, the 60’s, 70’s, and 80’s were a time of sexual liberation and exploration. I was pretty shy and awkward myself, but I managed some memorable sexual conquests. But I was also immature and screwed up my share of relationships too. Sometimes you wonder what it would be like if you had a do-over.

Anyways, I’ll start, there are a handful of memorable lovers I’ve had over the years. This is one chapter.

yes I have always about doing this but stopped for lack of time. They would have to be little vignettes -- five to six lines long. Wonder whether any one would be interested

 

[StrongMaster7]

A New England university - late 1970s - Lisa was a freshman who seemed to have no intention of getting a degree. I think she was in college for the social aspects. She was short and stacked, pretty face. We hooked up early in the year. The sex was good. After a few months, we broke up and she immediately went on a fucking spree. She fucked a number of guys I had introduced her to and a number of guys on her brother's hockey team.

I had totally gotten over her and didn't think about her much for a year or so. Then one day she showed up at my dorm. She had lost weight, started working out, bought all new clothes, grown her hair longer and was MUCH hotter than her already pretty attractive self. As hot as she was, I wasn't interested. She needed a date for a party with some 'fancy' people and she knew I had a suit. I went to her party in exchange for a quickie. It was quick, but good. I understand she got married shortly after that.

 

[Mike130]

This is Lynn with my sexual story:

Chapter one contains underage material.

Chapter two: Dating in high school with no sex. Gary promised me that he would not have sex with me until our wedding night because he loved me too much to risk getting me pregnant.

Chapter three: College. I only saw Gary once or twice a month and was free to date others. My dates discovered that two rum and Cokes made my inhibitions vanish, my clothes fall off, and my legs spread. I had lots of sex until the middle of my junior year when Gary and I decided I would not date anyone else.

Chapter three: Marriage. I took Gary’s virginity on our wedding night and we fucked seven times. Sex only with him until mid-30’s.

Chapter four: Mid-to late 30’s. Gary asked if I wanted to have sex with some of the men who were constantly after me I decided to try it, with certain conditions. I had sex with four younger men, one old college friend, and a 65-year old Russian doctor. When I turned 40, I stopped being with other men.

Chapter five: Just Gary and me. That says it all.

Actually one of the really true love stories on Lit

 

[lit_ch3]

One ex-gf looked up at me while sucking my cock. "Why don't you cum in my mouth?" she asked, just before taking my entire length down her throat. I thrust up, and unloaded. She took all of it, and then started shuddering uncontrollably.

Turned out, she would cum while sucking cock, without even touching herself. We tried 69 a bunch of times, amd failed every one. Each of us too sensitive giving the other pleasure that way.

 

[Mike130]

One ex-gf looked up at me while sucking my cock. "Why don't you cum in my mouth?" she asked, just before taking my entire length down her throat. I thrust up, and unloaded. She took all of it, and then started shuddering uncontrollably.

Turned out, she would cum while sucking cock, without even touching herself. We tried 69 a bunch of times, amd failed every one. Each of us too sensitive giving the other pleasure that way.

Wow! That’s so fucking hot!

 

[Mike130]

yes I have always about doing this but stopped for lack of time. They would have to be little vignettes -- five to six lines long. Wonder whether any one would be interested

This might be the place for those vignettes….

 

[Mike130]

Debbie B, Connecticut, 1970’s

Tall blonde, dick sucking lips, thin with a few curves. A bit of a nut. Was into fucking and blowjobs, but would never let me eat her out. We would go out for a period of time, stop, then hook up again 6 months or a year later. She was fun and intelligent, but also kind of vindictive. One time, she was mad at me for some reason and we went to this really nice restaurant, she ordered the most expensive thing on the menu, took one bite, and was done. That kind of thing.

Anyways, I had an apartment about 20 miles away from where she lived, and I gave her a key. One time, it must have been a week night, I had a FWB over, we had sex and she left. The next night I was alone, Debbie, let herself into the apartment quietly, took off all her clothes in the living room, then walked into my bedroom completely nude! A beautiful sight and we made love, but I couldn’t help but think that if she had pulled her surprise visit a day earlier it would have been a completely different story and I would probably be singing soprano.

Holy shit, dodged another one!

Our paths crossed again, years later, but we were both seeing other people so nothing came of it.

She got married, started a business with her husband, and remained in the area.

 

[Mike130]

Sadly, all my encounters didn’t end in wild sex, but some were funny.

Unknown girl, Connecticut, 1970’s

My friend visited my apartment, and I had never met his girlfriend. So he trudged up to my third floor apartment with a blow up sex doll. I opened the door and he said “I’d like you to meet my girlfriend Pat.”. We had a good laugh and he said he almost had a heart attack blowing the thing up.

So he left it in my apartment and I threw it in a closet and forgot about it. A couple of days later, I had a date with a girl I met the week before. She came over, and my place was pretty new, cathedral ceilings and decorated pretty well for a bachelor pad. She was really impressed, and started looking around, opened the closet door, saw the blowup sex doll (in retrospect I probably should have at least deflated it), and she was out of there in 5 minutes.

A swing and a miss.

 

[Justfantasies]

Vignette 1: Sydney

She was 18, I was 19. She had a crush on me. I figured she must be a virgin because she was religious -- but she wasn't a virgin. She was already three cocks away from being a virgin.

We went to see the original version of Alfie, which dates us both. It was about a seducer extraordinaire, with Michael Caine in the name role. It somehow gave me some dutch courage and turned me on. We parked behind the theater and Sydney let me unbutton her little red dress in my little red car. There wasn't much foreplay, but she let me pull her panties aside, put it in her and I came quite quickly -- it felt quite wonderful for me. Doubt that it did for Sydney. We were involved throughout that summer.

My relationships have always been polyamorous and this was the first. My friend Michael always wanted to get into Sydney's panties and eventually he did. It didn't seem to make much difference to me and Sydney and I went on fucking for a while.

Sydney married an accountant, who probably expected a nice virginal wife. I wonder how much he knew. Wonder what happened to her.

jf

 

[Justfantasies]

Bump ...

 

[Wageslave]

Many of you will be able to write epic volumes - mine is more of a single sheet of A 4

 

[Justfantasies]

Many of you will be able to write epic volumes - mine is more of a single sheet of A 4

Go ahead -- I want this chain to survive

 

[Wageslave]

Put it like this - pandas mock me for my lack of a sex life

 

[Justfantasies]

try -- how many?

 

[lit_ch3]

Put it like this - pandas mock me for my lack of a sex life

How about the best orgasm you had jerking off? It's still a chapter.

 

[lit_ch3]

This is from a story I submitted a long, long time ago. However, it's taken from a letter I actually wrote to my wife. And it's a true account of a session I had, by myself.

Dear -
As I mentioned in my last letter, for some months now I've been extremely randy for some reason. I can't seem to get sex off my brain. Yesterday, I experimented a little bit. I stroked myself several times without ever letting myself cum. Once in the shower, using a thick lather of soap, the second time while sitting at my desk, but last night in bed I finally let go. It was incredible! I lay there for a few minutes in the dark, and when I realized I wasn't going to get to sleep right away, I threw back the covers and turned on the light. You know how your mouth waters in anticipation of sex? How your heartbeat increases? Your breathing becomes heavier? I looked down and my cock was rock hard against my belly, and throbbing in time with my pulse.

The head was a dark red color. I grabbed the base with one hand, and with the other gathered up some saliva from my lips. I then rubbed just the top of my penis with the saliva, making it glisten in the light. The pre-come was already starting to leak from the tip, and I swirled that into the spit to add to the slippery feel. I pushed myself back into the pillows, bent my knees and spread my legs apart. The cool air rushed in under my balls and made them tighten up even more than they already were. I encircled the head with my thumb and forefinger and slowly slid them down to just under the corona, squeezing just a little tighter as I went over the ridge. As I squeezed the base a little harder, the head turned almost purple and I concentrated my other hand on that. After just a few strokes, I felt the pressure building up inside my balls. Having held back a couple of times already today, I clenched my butt muscles to hold back for just one more stroke, then I let go. The release was incredible, shooting cum over my shoulder and onto the pillow. The rest landed on my chest and stomach. After a moment I scooped it up onto my fingers and swallowed it. It was still warm – I do like the taste of my cum.

 

[Justfantasies]

Vignette 1: Sydney

She was 18, I was 19. She had a crush on me. I figured she must be a virgin because she was religious -- but she wasn't a virgin. She was already three cocks away from being a virgin.

We went to see the original version of Alfie, which dates us both. It was about a seducer extraordinaire, with Michael Caine in the name role. It somehow gave me some dutch courage and turned me on. We parked behind the theater and Sydney let me unbutton her little red dress in my little red car. There wasn't much foreplay, but she let me pull her panties aside, put it in her and I came quite quickly -- it felt quite wonderful for me. Doubt that it did for Sydney. We were involved throughout that summer.

My relationships have always been polyamorous and this was the first. My friend Michael always wanted to get into Sydney's panties and eventually he did. It didn't seem to make much difference to me and Sydney and I went on fucking for a while.

Sydney married an accountant, who probably expected a nice virginal wife. I wonder how much he knew. Wonder what happened to her.

jf

One final bump

 

[Nellie60]

Masturbation 101

A GF for a brief time, early 80’s, I was late 20’s, she was a couple years younger. It was a lust at first sight relationship.

We were lying in bed; she was almost on her side, tucked under my right arm, leaning on my chest, face very close. I was flat on my back, head on a pillow, rock hard with her stroking me slowly. When I moaned about it feeling so good she stopped and let go. Very quietly she asked “what does it feel like when you touch yourself”. I knew right away she wanted to watch me jerk off which she had claimed previously to have never seen before.

I showed her everything I could think of and explained what I was doing as I was doing it. Tugging my balls (they were loose because of the heat), rubbing my knob in a circular fashion, and stopping to stare at how hard I was when holding myself straight up. And of course my own method of ejaculation control, strokes slowing more and more as my orgasm approached threshold limit of no return.

She dipped one hand between her legs and said “am I ever wet”. I asked for a taste so she dipped again and offered two fingers to my mouth. Looking her in the eyes, I used my tongue to clean her juice off. I commented on her taste and said she should try some. She hesitated but did dip her fingers again then raised them to her mouth to lick them clean.

I had slowed down my stroking but was ready to blow, I knew it would be a good one but still did not expect what shot out. The first rope hit me from chin to forehead, some into my hair and then the headboard behind us. Not expecting so much, she flinched a bit and the next ropes again hit my cheek and her forehead, a couple drops landing on her shoulder. Then a few more spurts on my abdomen, plus lots on my hand and limp cock.

I licked my fingers clean as she watched and rubbed her clit.

She said that show changed her mind about guys jerking, it was a lot more than just beating off.

BTW . . . she was the wettest woman I had ever been with up to that time. She would gush juice out when riding me cowgirl and grinding her clit on my pubic bone. If I had known what I do now, I could have gotten some fantastic squirts from her.

Masturbation 101

A GF for a brief time, early 80’s, I was late 20’s, she was a couple years younger. It was a lust at first sight relationship.

We were lying in bed; she was almost on her side, tucked under my right arm, leaning on my chest, face very close. I was flat on my back, head on a pillow, rock hard with her stroking me slowly. When I moaned about it feeling so good she stopped and let go. Very quietly she asked “what does it feel like when you touch yourself”. I knew right away she wanted to watch me jerk off which she had claimed previously to have never seen before.

I showed her everything I could think of and explained what I was doing as I was doing it. Tugging my balls (they were loose because of the heat), rubbing my knob in a circular fashion, and stopping to stare at how hard I was when holding myself straight up. And of course my own method of ejaculation control, strokes slowing more and more as my orgasm approached threshold limit of no return.

She dipped one hand between her legs and said “am I ever wet”. I asked for a taste so she dipped again and offered two fingers to my mouth. Looking her in the eyes, I used my tongue to clean her juice off. I commented on her taste and said she should try some. She hesitated but did dip her fingers again then raised them to her mouth to lick them clean.

I had slowed down my stroking but was ready to blow, I knew it would be a good one but still did not expect what shot out. The first rope hit me from chin to forehead, some into my hair and then the headboard behind us. Not expecting so much, she flinched a bit and the next ropes again hit my cheek and her forehead, a couple drops landing on her shoulder. Then a few more spurts on my abdomen, plus lots on my hand and limp cock.

I licked my fingers clean as she watched and rubbed her clit.

She said that show changed her mind about guys jerking, it was a lot more than just beating off.

BTW . . . she was the wettest woman I had ever been with up to that time. She would gush juice out when riding me cowgirl and grinding her clit on my pubic bone. If I had known what I do now, I could have gotten some fantastic squirts from her.

I had pretty Eastern European gf years ago. She would have been late twenties. Petite, slim abt 5 foot 5 so very attractive to me. Jenny I think.

The first sexual contact very memorable and surprised me. Saw each other for a few dates. After one particular date she invited me to her flat. I thought this was it. Only ever kissed her on one occasion and nothing else so sort wasn't expecting much. Ask to use her ensuite bathroom. Came out and she was lying on her bed still clothed spread eagled. Of course my eyes were "popping out of them sockets" She was had a nicely trimmed hairy pussy.

Sexy smile on her face and she just spread her pussy wide with her hands as she looked at me. I just did what I was expected to do. I moved her to edge of bed, knees on floor and she held her legs wide open and using my hands to spread those very wet labias and went down on her. The smell and taste was one of the more memorable part. I didn't think she showered recently. Didn’t put me off so turned on. She started moaning straight away. Held the back of my head firmly and proceeded to gyrate and ride my face rapidly and had an immediate orgasm. She squirted cause all of a sudden the taste was different. Disappointingly I came myself! got so worked up you know. Very memorable like I said.

After that fucked her for a few weeks and then she disappeared. No reason? Still don't know until this day. Would love to do it again

 

[Nellie60]

Have you ever thought about writing a story of your sexual past? Maybe there are partners in your past that you’ve had a sexual or deeply emotional connection that you really can’t share with your current partner, but you remember fondly. Maybe Literotica is the place you can reminisce.

For older members, the 60’s, 70’s, and 80’s were a time of sexual liberation and exploration. I was pretty shy and awkward myself, but I managed some memorable sexual conquests. But I was also immature and screwed up my share of relationships too. Sometimes you wonder what it would be like if you had a do-over.

Anyways, I’ll start, there are a handful of memorable lovers I’ve had over the years. This is one chapter.

Here's another on on Sandra C. Written abt her before. Love of my life. This happened several years ago. Went out with her for about 2 years until she had an affair with a friend. Still hurts.

But I still wtite and fantasy about this girl. Very attractive Asian of Korean descent. Petite and probably 5" 4. Very nice personality. Friendly, confident and feminine in nature.

First sexual encounter into 2nd date. In car gave me an unexpected (or sort wanted this to happen) incredible handjob. Lots of making out kissing and accumulating in a furious handjob in the front seat. One of the most memorable. She was just intense and enthusiastic what can i say. Now I got this fetish thanks to her.

I have seem her a couple occasions around. I think she married now. Would love to....