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Fondest Sexual Experience

bookworm69 said:
This occurred many years ago. I was a lowly intern at work and she was an established and highly regarded secretary, who was four years older than me. She was divorced and had a child .. suffice it to say, she was "an older woman." I considered her a work friend, although I was not blind to her womanly charms. About a year in, she invited me to a not-quite formal function. I had to wear a jacket and tie and she was going to wear a snazzy dress. Her child was being babysat elsewhere. I was in total friend mode when she called me into her bedroom to zip her dress up from the back. I zipped her up and we went out to the function. However, when we returned after the function she started to cry. She was crying because her attempt to seduce me ... failed. Of course, I made things right that night ... and slept over.

We had great sex for a few years, but I often think how naive I was ... when sex, something I was always looking for, fell into my lap without any effort on my part.
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We all had to start somewhere .
 
I think I’ve written about it in the past. College girlfriend and I were moving together to Minneapolis, and had stopped in River Falls WI for the night. We hit the pool and hot tub after a long day of driving, she playing footsie with my dick in the hot tub under the bubbles. We get back to room an dry off, me with an amazing erection.

She loved to slip the condom onto me, so she does and we settle into a very passionate lovemaking session. I feel the inevitable orgasm starting to rise, and right at exact moment of my orgasm, she clenches her pc muscle, hard. The surprise of this took my breath away. She said my eyes about popped out of my head.

None of my other girlfriends had done that before.

She explained afterwards that driving up there, if she passed a car with an out of state plate, she’d squeeze herself a number of times. After that session it’d be a regular thing where when I’d slide inside her, she’d tell me not to move, let her do the work. If she’d be on top, it’d almost end that way.

I miss her
 
Pabiporffor said:
For me, it was just a simple thighjob. I was a virgin at the time, but I had done a couple of BJs, so I wasn't entirely naive. Fun as they were, they only lasted a few mins. The thighjob was the first time I'd been fully naked with a man in bed. He was more than a few years older but still attractive. I admit I was a little nervous, but knowing I wasn't going to be penetrated really helped me to relax.

Unlike the BJs where the guys were just interested in spray painting my tonsils, I was with a guy wanting to give me pleasure as much as have his own. It was unrushed with a ton of foreplay and as I grew more and more aroused any nerves I had slipped away.

The actual sex part was a mix of having him trapped between my thighs or with my legs apart and him simply gliding along the valley, I found the second far more pleasurable and not too different to when I'd rub myself although a lot more intense and intimate.

He finished with my legs pushed back, and squeezed together as he leaned over me. I felt him trembling, and things got kinda sticky. After a quick clean up, I experienced my first oral sex to orgasm which admittedly didn't take long. Apart from the orgasm what made it my fondest experience was it really boosted my sexual confidence and trust in men.
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Has this experience made you more attracted to older men?
 
friendlytongue38671 said:
I think I’ve written about it in the past. College girlfriend and I were moving together to Minneapolis, and had stopped in River Falls WI for the night. We hit the pool and hot tub after a long day of driving, she playing footsie with my dick in the hot tub under the bubbles. We get back to room an dry off, me with an amazing erection.

She loved to slip the condom onto me, so she does and we settle into a very passionate lovemaking session. I feel the inevitable orgasm starting to rise, and right at exact moment of my orgasm, she clenches her pc muscle, hard. The surprise of this took my breath away. She said my eyes about popped out of my head.

None of my other girlfriends had done that before.

She explained afterwards that driving up there, if she passed a car with an out of state plate, she’d squeeze herself a number of times. After that session it’d be a regular thing where when I’d slide inside her, she’d tell me not to move, let her do the work. If she’d be on top, it’d almost end that way.

I miss her
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That does sound like a great memory. I've only had one gf do that on purpose (some have coughed or even sneezed) while I was inside them, and I naturally have to ask - 'could you do that again... please?' lol
 
Unsere Hochzeitsnacht mit meinem Vater und wo der erste schwarze Schwanz in ihre Möse gesteckt wurde. Das sind tolle und prägente Erlebnisse gewesen
 
Mine has to be the very first blowjob I ever received, given to me by my future and current wife who also took my virginity a little while later.

I was a late bloomer at having sex so to speak, because despite being attractive to women and exuding confidence I was always terrified of letting a woman see how small my erection is. After dating my wife for months she got tired of waiting for me to make a move and did it herself.

Like most guys I climaxed quickly after she took me into her mouth, probably less than a minute. I was humiliated because of how fast it was, but even though I warned her I was about to cum she sucked me through my entire orgasm and swallowed every drop.

I thought it was over at that point, but she reassured me that she wasn't done and to just lay back and relax. So I did.

For the next 30 minutes or so she proceeded to lick and suck my balls, tease my perineum with the tip of her tongue, and demonstrate oral skills that no "innocent" girl could possibly have. I got hard again, and she gave me the most exquisite blowjob until I came in her mouth again. She swallowed every drop the second time, too, sucking hungrily during each ejaculation.

It was life changing for me, in a good way.

I knew deep down inside that wasn't the first blowjob she had ever given, but it didn't matter to me. I was the recipient of her skill and expertise and it made me feel like a king. Of course my curiosity about her past sexual experience has fueled my fantasies of her for years but's that another story...
 
Whispor said:
Mine has to be the very first blowjob I ever received, given to me by my future and current wife who also took my virginity a little while later.

I was a late bloomer at having sex so to speak, because despite being attractive to women and exuding confidence I was always terrified of letting a woman see how small my erection is. After dating my wife for months she got tired of waiting for me to make a move and did it herself.

Like most guys I climaxed quickly after she took me into her mouth, probably less than a minute. I was humiliated because of how fast it was, but even though I warned her I was about to cum she sucked me through my entire orgasm and swallowed every drop.

I thought it was over at that point, but she reassured me that she wasn't done and to just lay back and relax. So I did.

For the next 30 minutes or so she proceeded to lick and suck my balls, tease my perineum with the tip of her tongue, and demonstrate oral skills that no "innocent" girl could possibly have. I got hard again, and she gave me the most exquisite blowjob until I came in her mouth again. She swallowed every drop the second time, too, sucking hungrily during each ejaculation.

It was life changing for me, in a good way.

I knew deep down inside that wasn't the first blowjob she had ever given, but it didn't matter to me. I was the recipient of her skill and expertise and it made me feel like a king. Of course my curiosity about her past sexual experience has fueled my fantasies of her for years but's that another story...
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Wow, 🤩, nothing beats being introduced to sex by a more experienced lover. I am glad that I worked out for you.

Her past seems interesting, ever thought of making a story out of it? Provided, of course, that you would want to share it.
 
Vitriolhack said:
Wow, 🤩, nothing beats being introduced to sex by a more experienced lover. I am glad that I worked out for you.

Her past seems interesting, ever thought of making a story out of it? Provided, of course, that you would want to share it.
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She was with one guy before me, and older guy, for about three years when she was 19-22. It was many years into our marriage when she let it slip that he had a "huge, huge cock" one night when she was tipsy. Ever since I have fantasized about how she licked and sucked that big cock, swallowed its cum, and how powerfully she used to orgasm when it impaled her.

I wish I could get her to talk about her experiences, but she hates the guy because of how the relationship ended and it soured all of her feelings for him. I don't think she can reminisce about the pleasure they shared without it stirring up that resentment. I'd love to listen to her telling me about it while she's giving me a hand job to "demonstrate" how much her past experiences with that big cock turn me on.
 
Whispor said:
She was with one guy before me, and older guy, for about three years when she was 19-22. It was many years into our marriage when she let it slip that he had a "huge, huge cock" one night when she was tipsy. Ever since I have fantasized about how she licked and sucked that big cock, swallowed its cum, and how powerfully she used to orgasm when it impaled her.

I wish I could get her to talk about her experiences, but she hates the guy because of how the relationship ended and it soured all of her feelings for him. I don't think she can reminisce about the pleasure they shared without it stirring up that resentment. I'd love to listen to her telling me about it while she's giving me a hand job to "demonstrate" how much her past experiences with that big cock turn me on.
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That is a hot story, knowing he has a huge cock is a turn on. Alas, better not bring up bad memories, they could ruin the present!

😉
 
God, this is a hard one to nail down. I think for me it has to be the first time i was invited to a swing party with my mom and dad. I knew they were swingers, and knew they attended parties each month, but although we were sexually involved, I had never been to anything like that. I was young, very enthusiastic, full of questions... I know they were regretting even asking me by the day of the party. lol. Mom had took me shopping for some of the naughtiest outfits I'd ever had, set me up at the hair salon, all that sort of stuff. I think they were more excited than me. lol.. Anyway, I was so nervous and self-conscious and finally mom asked me to follow her. She whispered about us doing something to help me get started. I followed her down a hallway and there were rooms on bth sides, some with doors open, some closed, some with windows, one had a group of 4 or 5 people, naked all intertwined in each other, others had just couples, some rooms you could hear the mans behind the closed doors. At the end of the hall mom stopped with her hand on a doorknob. She smiled and winked at me and said "So, are you ready to have some fun", and I nervously whispered, "Yes ma'am, I think I am". She turned the knob and pushed the door open and ushered me in. The walls of the room were solid black, padded, and the floor was a swirl of red and gold paint, almost like tie dye, there were gold lamp fixtures hang from the ceiling, and some funky punk rock music coming through high mounted speakers. The padded walls were individual panels, and each panel had a neat hole in it about waist high. 14 in total to be exact. Glory holes. I had never seen glory holes, but God I always wanted to be in a glory hole room. There were 3 women in there already, two were completely naked. Mom just said "Have fun hunny" and dropped to her knees and started sucking a cock. I fell to my knees right beside her and grabbed this fat cock and just devoured it. I was so turned on. The woman next to me was probably mom's age or older and she was fingering herself furiously as she sucked a huge black cock. The sounds of everyone, all strangers just going after these cocks, naked, half naked, fully dressed, more women coming in, and cocks everywhere, was just so unbelievably hot to me. I orgasmed so hard on my own hand as I watched my beautiful mother get sprayed with some stranger's spunk. Her top was down and it was dripping off her face and onto her tits. I had so much fun that night. We made out with other women, licked cum off each other, and laughed our asses off. And that was before the real fun even got started. It was an awesome night I'll never forget.
 
Deadygirl said:
God, this is a hard one to nail down. I think for me it has to be the first time i was invited to a swing party with my mom and dad. I knew they were swingers, and knew they attended parties each month, but although we were sexually involved, I had never been to anything like that. I was young, very enthusiastic, full of questions... I know they were regretting even asking me by the day of the party. lol. Mom had took me shopping for some of the naughtiest outfits I'd ever had, set me up at the hair salon, all that sort of stuff. I think they were more excited than me. lol.. Anyway, I was so nervous and self-conscious and finally mom asked me to follow her. She whispered about us doing something to help me get started. I followed her down a hallway and there were rooms on bth sides, some with doors open, some closed, some with windows, one had a group of 4 or 5 people, naked all intertwined in each other, others had just couples, some rooms you could hear the mans behind the closed doors. At the end of the hall mom stopped with her hand on a doorknob. She smiled and winked at me and said "So, are you ready to have some fun", and I nervously whispered, "Yes ma'am, I think I am". She turned the knob and pushed the door open and ushered me in. The walls of the room were solid black, padded, and the floor was a swirl of red and gold paint, almost like tie dye, there were gold lamp fixtures hang from the ceiling, and some funky punk rock music coming through high mounted speakers. The padded walls were individual panels, and each panel had a neat hole in it about waist high. 14 in total to be exact. Glory holes. I had never seen glory holes, but God I always wanted to be in a glory hole room. There were 3 women in there already, two were completely naked. Mom just said "Have fun hunny" and dropped to her knees and started sucking a cock. I fell to my knees right beside her and grabbed this fat cock and just devoured it. I was so turned on. The woman next to me was probably mom's age or older and she was fingering herself furiously as she sucked a huge black cock. The sounds of everyone, all strangers just going after these cocks, naked, half naked, fully dressed, more women coming in, and cocks everywhere, was just so unbelievably hot to me. I orgasmed so hard on my own hand as I watched my beautiful mother get sprayed with some stranger's spunk. Her top was down and it was dripping off her face and onto her tits. I had so much fun that night. We made out with other women, licked cum off each other, and laughed our asses off. And that was before the real fun even got started. It was an awesome night I'll never forget.
Click to expand...
Sounds like you had a good time.
 
Deadygirl said:
God, this is a hard one to nail down. I think for me it has to be the first time i was invited to a swing party with my mom and dad. I knew they were swingers, and knew they attended parties each month, but although we were sexually involved, I had never been to anything like that. I was young, very enthusiastic, full of questions... I know they were regretting even asking me by the day of the party. lol. Mom had took me shopping for some of the naughtiest outfits I'd ever had, set me up at the hair salon, all that sort of stuff. I think they were more excited than me. lol.. Anyway, I was so nervous and self-conscious and finally mom asked me to follow her. She whispered about us doing something to help me get started. I followed her down a hallway and there were rooms on bth sides, some with doors open, some closed, some with windows, one had a group of 4 or 5 people, naked all intertwined in each other, others had just couples, some rooms you could hear the mans behind the closed doors. At the end of the hall mom stopped with her hand on a doorknob. She smiled and winked at me and said "So, are you ready to have some fun", and I nervously whispered, "Yes ma'am, I think I am". She turned the knob and pushed the door open and ushered me in. The walls of the room were solid black, padded, and the floor was a swirl of red and gold paint, almost like tie dye, there were gold lamp fixtures hang from the ceiling, and some funky punk rock music coming through high mounted speakers. The padded walls were individual panels, and each panel had a neat hole in it about waist high. 14 in total to be exact. Glory holes. I had never seen glory holes, but God I always wanted to be in a glory hole room. There were 3 women in there already, two were completely naked. Mom just said "Have fun hunny" and dropped to her knees and started sucking a cock. I fell to my knees right beside her and grabbed this fat cock and just devoured it. I was so turned on. The woman next to me was probably mom's age or older and she was fingering herself furiously as she sucked a huge black cock. The sounds of everyone, all strangers just going after these cocks, naked, half naked, fully dressed, more women coming in, and cocks everywhere, was just so unbelievably hot to me. I orgasmed so hard on my own hand as I watched my beautiful mother get sprayed with some stranger's spunk. Her top was down and it was dripping off her face and onto her tits. I had so much fun that night. We made out with other women, licked cum off each other, and laughed our asses off. And that was before the real fun even got started. It was an awesome night I'll never forget.
Click to expand...
You are a dream girl
 
Whispor said:
She was with one guy before me, and older guy, for about three years when she was 19-22. It was many years into our marriage when she let it slip that he had a "huge, huge cock" one night when she was tipsy. Ever since I have fantasized about how she licked and sucked that big cock, swallowed its cum, and how powerfully she used to orgasm when it impaled her.

I wish I could get her to talk about her experiences, but she hates the guy because of how the relationship ended and it soured all of her feelings for him. I don't think she can reminisce about the pleasure they shared without it stirring up that resentment. I'd love to listen to her telling me about it while she's giving me a hand job to "demonstrate" how much her past experiences with that big cock turn me on.
Click to expand...
Sounds sadly familiar .
 
Once, when I was still married to my ex, she and I argued in the room that was our home office at the time. Somehow, I don't remember the exact details, we stopped arguing and fell into each other's arms right there in the middle of the room's doorway. We sank to the floor, made out, undressed a bit, stroked each other to orgasm. It's true what they say about make up sex being great.

A few years later we got divorced. But, for that moment, I was hopeful and happy. I like to think she was too.
 
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