Do You Remember Your Three Best Orgasms? Masturbating, Oral Sex, and Fucking?

Masturbating​

Well for that I have to say the very first prostate orgasm was by far the best orgasm ever and didn’t touch my dick once during that. I barely could stand during and after it happened in the standup shower​

Oral Sex​

I would have to give that credit to a woman by the name of Michelle my first GF after divorcing my wife. First day we met we were chatting for about two hours and she said she had to go get her son. I had to kiss her before she left which turned out to a make out session which during it I pulled out my hardon and she attacked that thing like it was her last meal. However I didn’t have an orgasm for five days so that may have contributed to it but she was also sucking that thing like a human vacuum cleaner. When I was seconds from cumming I tried to warn her but I literally couldn’t get the words out. She kept sucking after I came but I had to pull her off because I was sensitive after. We dated for two years which was some of the best sex of my life .​

Fucking​

For this category I have to give two. They are equally number one but equally different. I’ll list them in order of which one happened first.

I’m in my bedroom in my parents house that I was still living in. Relax moderators I was at least 21 at this time. I have to be at the food store in a little bit for work so my GF which later became my wife which later became my exwife I was fucking. Nothing special just straight missionary sex. I have no idea why but I came so hard so intense when I say I saw stars I am not exaggerating. Best I can describe it is spots of light like little dots of light everywhere.

It was so intense my legs were like jello and I was out of it for at least a hour. First hour at work people were asking if I was okay and I just smiled and said yeah.

Second one is with that mom Michelle. It was New Years Eve. I don’t even think we were officially a couple anymore. Regardless the night ended with sex. I am talking about pure fucking that went on for a while. Must have been the alcohol that allowed me to last as long as I did. It ended with her laying flat on the bed but her ass sticking out just enough so I could fuck her asshole. The final minutes of it I grab my window sill which the bed is right next to and elevated my body and used my entire body weight to slam my cock in her. Eventually I came and when I say I came I came hard. I swear it was like being in a porno.

So I lay on my side behind her and she too rolled on her side and we are both trying to catch our breath. At some point I just say “That was the fuck of the year”. She replies not with words but nodding her head up and down fast.

The two of us had some great sex together but that was the best one by far.
 
I posted mine earlier. My wife says her most memorable was the first time I ate her pussy. She had never had that experience and had an explosive orgasm. The next was when she straddled my face while I ate her and she sprayed all over me. The third was the first time she had an orgasm from just fucking. it was in college with her best college lover.
 
Masturbating:
My best masturbatory orgasm came after a decade-long stint of not masturbating at all (I was still sexually active, just not on my own). I had been doing a lot of writing of stories for lit and shopping for lingerie and sex toys. One sex toy included an "instructional video" which was really just a porno involving the toy. I hadn't watched any porn in a while, and I was super horny from everything else. Just the throbbing of my cock in my pants caused enough friction for my orgasm to trigger. It was all I could do to get my pants down before I started spurting a massive load all over myself. It felt so uncontrollably good that I've been back to masturbating daily ever since!

Oral:
I met a crossdresser on Craigslist and went over to her apartment to dress together. We posed for pictures together, rubbed each other, caressed each other, for about an hour. Poor girl was so nervous she couldn't get hard, but I had no trouble with that. I ended up grinding between her cheeks, her thong and my panties keeping our flesh from touching. I asked if I could take my cock out. She said yes. After sliding it between her cheeks two or three times, she wordlessly dropped to her knees and took me into her mouth. She sucked me so eagerly, and I was so turned on from everything so far (and from watching her suck me as I videoed it), I didn't last long. As I was caressing her wig and the back of her head, it was all I could do to not just start face-fucking her. Instead, I warned her I was about to cum and she backed off at the very last moment, leaving me to spray her face and wig with rope after rope of cum. I blasted one right into her eye and she ran off, leaving me still shooting all over the floor.

After she had cleaned out her eye, she came back and helped me clean up. I apologized, and she said the facial was the best part, except for the stinging in her eye. She confessed it was her first bj, though I couldn't tell.

Sex:
The best orgasm I ever had from fucking someone was the first time I had anal sex. It was also my wife's (then girlfriend's) first time, although we'd been dancing around it with rimming and fingering during oral for quite some time. One day after wearing her pussy out for an hour or so, she asked if I wanted to try anal. Duh.

We took our time, with lots of licking, fingering, and lubing. Then I put it in. I have a relatively fat head, and even after stretching her with two fingers first, she gasped when it popped in. It took all my willpower to go slow, but I managed out of love and desire for it to not be just once. By the time I was balls deep, she was wiggling her ass side to side and moaning. She ended up prone with me on top, kissing passionately as I slowly slid in and out while pinning her wrists against the mattress. I ended by just fucking her with the front half of my dick, so my head was constantly squeezed tightly, until I slid in completely just as I started to cum. For being my third orgasm of the night, I still shot quite a bit into her as my toes curled and my eyes rolled back into my skull.

Epilogue to that: when I got back home that night, I immediately put on some anal porn and jerked off thinking about what had happened. I was hard the whole drive home.
 
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Just wanted to dust this off for anyone else who wanted to contribute.


Masturbation: possibly my first prostate orgasms. I managed to achieve it, and had 7 in under an hour. I was a sticky, soaked mess, unable to walk or breathe properly. I then straight wanked to finish. All while ex wife and was upstairs asleep. I was dehydrated and exhausted.

I have had some lengthy solo edging sessions, and straight wanks that have been mind-blowing too.

Handjob: had a FWB when I was about 18/19, she was my then GFs best friend. We were on the sly. She edged me for hours teasing as I fingered her to numerous orgasms. She made me blow everywhere.

Blowjob: going to be either one from current GF as she rode my face... Or a bi experience. Gay guy. Waiting naked. Literally walked in, got sucked dry. I could barely breathe.

Fuck; current GF. She's built to fuck, and has the tightest pussy ever. Been a couple of doggy style finishes after lengthy foreplay thatve led to me gasping.

Anal: ex wife. When submissive and struggling with MH she craved anal, we had some wild fucks.
 
We all have unforgettable sexual encounters, memorable for a variety of reasons. But do you remember the single best ORGASM you ever had...?
No. I don't. Perhaps I have lived too long. Perhaps I have enjoyed too many encounters. But I couldn't even say with whom I had my 'best' orgasm. :D
 
We all have unforgettable sexual encounters, memorable for a variety of reasons. But do you remember the single best ORGASM you ever had while masturbating, while getting your cock sucked or your pussy eaten, and while fucking? Please share your stories of the orgasms that you will never forget. Pic/video link examples of your experiences encouraged!

1. Masturbating. This one time I masturbated naked right in my bedroom window while my teacher, who lived next door, was mowing her lawn. It was a hot day, she was wearing a thin summer dress and I could see her black panties through it. I was terrified she'd look up and see me but I was so aroused I couldn't stop and the possibility of being caught just turned me on even harder. I came so hard my balls hurt, spraying my semen all over my bed and floor.

2. Blowjob. With a married woman I was seeing on the DL. She was beyond a doubt the best at all things sexual I'll ever know, although she was also flaky as hell emotionally and it ended badly. Anyway, while it was good, she blew me one time and really went to work on my cock, sucking the head hard while wanking my shaft vigorously. Right as I was about to cum, she raked her teeth lightly over my glans, and that tipped me over the edge. I exploded into her mouth and she held the cum there and let it coat my raw and sensitive cock head while I was still pumping. It seemed to go on forever, like I wasn't just draining my balls but some deep reservoir of semen I'd not previously discovered, and I actually passed out momentarily from the sheer intensity of the feeling, my cock on fire and my balls aching. And she swallowed the lot.

3. Fuck. I've told this elsewhere but it was on a camping holiday with my ex. Our two kids had wandered off somewhere on the (safe, family-oriented) campsite to play and we were both as horny as hell; no foreplay, we just got naked as fast as possible in the tent and I got on top of her and hauled her legs over my shoulders, pinned her wrists and guided my cock in then immediately started humping and thrusting deep as she was already wet. It was fast, intense and her erect-nippled tits were rolling as I pumped my cock hard and balls-deep into her hairy pussy, and we came together, eyes locked, my final thrust so deep I could feel her cervix twitching (and I swear it felt like sucking) on my cock head as I emptied myself of a huge load of sperm and her pussy clenched on my shaft. Our third daughter was born 9 months later and I realised once we knew she was pregnant that that had been the fuck of creation, no question.

I'd seen a Desmond Morris show years before on human sexuality where they'd somehow managed to place an internal camera to capture a woman's cervix during orgasm and shown it doing that same involuntary sucking motion I'd felt on my cock head, as nature's way of optimising conception, and knew that that was what had happened.
 
I think about this when you dust it off. And I just can't come up with "the best". So many good ones. Been a while. The last recent most memorable was actually a masseuse that owed me a favor. My previous massage was interrupted.
45 minutes focused on the major pleasure points before she finally held on and let me release. She followed direction too. Don't change anything. Don't squeeze different, speed up or slow down. Or worst do not stop. hahaha
I am thinking she did not think I had it in me. There was a few shots of cum on the dresser in front of the table. After those she tried to contain it a little and there was cum on her shirt in her hair on her face.... She was laughing. I was catching my breath and nearly passed out.
 
I'm going to sound like the most pathetic being on earth...

My only really great orgasms have come (cum?) at my own hand. My husband of 25 years... I'll just say that sex was not his forte. I've never been fucked (ever) and I can't remember ever having an orgasm from oral sex, though I've done more than my share for him. That's not the point here, though.

It might have been a year ago. I was alone out here in my recliner, and it had been a while since I'd even touched myself, much less orgasmed. The sensation was intense right away, but I tend to enjoy savoring these things, so I edged for a while. I couldn't tell you how many times, but it was more than I could count on all fingers and toes. When I finally decided I was ready, I let my toy run its most intense pre-made program and sat back. The feeling started as a tingle in the pit of my stomach, radiating outward. I'd really never felt pleasure quite like it before. The toy continued to run, increasing and slowing in pace and intensity at frustrating intervals until it finally hit a steady, powerful rhythm. If I could have screamed, I would have. It was a toe-curling, thigh-shaking, full body, I-think-I've-died-and-gone-to-heaven kind of feeling. The spasms came in waves, and though it was an intense orgasm, the waves of pleasure were gentle, like water lapping at your toes with an incoming tide. Just as I thought it was over, another one snuck up on me and started the spasms all over again. When I finally decided I'd had enough, I was literally trembling, soaked with sweat, and breathless.

I slept like a baby that night.
Very vivid account. Liked it very much!
 
Masturbating- met woman, eight years older on an adult dating website, went to her condo, and we sucked and fucked for an hour. At the end, I pulled out, ripped off the condom, and masturbated, until it exploded all over her face, hair and tits. One of the biggest orgasms of my life. I didn’t even know her name…..

Oral: well, at a training course in Kansas City, had been chatting with a woman who was 10 years younger than me. After she put her daughter to bed… She was a single mom… She invited me over to her house. We proceeded to watch a movie during the movie, my cock got hard, she got on her knees, deep throat me, and proceeded to give me the best blowjob of my life, she was curvy, sexy, and busty, she titty fucked me and then sucked me all the way down until I blew my load down her throat .

Fucking: the day I lost my virginity, I can still remember the pleasure of sinking my bare, hard cock into the tight wet pussy of my girlfriend. Her legs wrapping around me as I gave it to her good slow and deep. Up until that point we had everything but fuck, so I did have stamina to last. fucked her for an hour before I spilled my load deep inside her.
 
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FUCKING
My wife had an affair with her college boyfriend 15 years ago. When she finally admitted it, I was hurt and angry. I thought about filing for divorce, but because we still had a child at home, I didn't. I did move into the guest room and we went into counseling, but I had no interest in a physical relationship. Then, one weekend afternoon, about 4 months later, she was in the kitchen. I came up behind her and spun her around, kissing her and cupping her ass. I dragged her into the living room and pushed her down on the couch and mounted her. We were frantically pulling each other's clothes off. I plunged my cock deep into her cunt and fucked her like an animal, all my hatred, anger and depression channeling though with every thrust. She was biting my neck and shoulders and and digging her nails into my arms and back, even drawing blood. No words were spoken. I finally came, pumping my load deep into her and collapsed on top of her, both of us covered in sweat. We stayed together, but the sex as never been as hot it was that afternoon and for the next few months.

HANDJOB
I know the post asked for the best oral orgasm. Unfortunately, I've never been in a relationship with a woman who particularly enjoyed oral sex. I've had my share of blowjobs, but only as foreplay. But I do recall one amazing handjob. (AND YES, MR. MODERATOR, BOTH THE GIRL AND I WERE OVER 18 WHEN THIS HAPPENED). It was my senior year. I had a respectable girlfriend at school, but I also had a "church girlfriend." Every Sunday and Wednesday night, after services, I would drive to the lake outside our small town and we would makeout like the horny teenagers we were. These sessions involved a lot of dry humping, fingerfucking, pussy eating and handjobs. Normally, I would go down on her, get her off, and she would return the favor with a handjob in the front or back seat of my 1969 Pontiac Bonneville. She would take my cock in her hand, stroke me to orgasm, then grab a tissue out of purse and clean up the mess. One night, she deviated from this routine. We made out, then I knelt on the floorboard, pulled down her pantyhose and panties far enough to go down on her and tongue her clit and finger fuck her. After she came, I crawled up on the seat next to her, expecting the usual handjob. This time, though, instead of roughly jerking my cock she placed it on her thigh and began rubbing it up and down her pantyhosed thigh. The sensation of my cock on the nylon and occasionally on her fleshy upper thigh was mindblowing. I shot my load on her leg and belly. Instead of retreiving a tissue, though, she scooped up the jizz and rubbed it into her breasts, then sucked her fingers and said "Yum." It was, at that time (and frankly still is) the sexiest thing I've ever seen. I have no idea where a girl in the sticks in West Texas in 1974 got the idea to do that...By the way, if you've looked at my posts in other forums, you know I have a pantyhose fetish. Do you wonder why?

MASTURBATION
Fast forward 25 or 30 years. I considered myself 100% heterosexual. I don't recall ever feeling attracted to men until one day when I went to pick up my daughter and her friend at a local swimming pool. I walked toward the pool and two college-age life guards were walking past me. Smooth, muscular bodies, six packs, bronze skin, water from the pool clinging to their bodies, dripping down the front of their trunks to the thighs. I collected the girls and dropped the friend at her house. As soon as we got home, I told my daughter I wasn't feeling well. I locked the bedroom door, stripped and laid down, my head at the foot of the bed, my feet in the air, braced agains the headboard. My cock was rock hard. I fantasized about being on my knees, licking and kissing and sucking my way down those gorgeous bodies to those hot, young cock. It didn't take long. My back arched and the first spurt went over my shoulder and some of it hit my cheek and neck. The second spurt hit me in the chest and the poured out of my hole and ran down my shaft, pooling at the base of cock. So fucking good. I still haven't sucked a cock, but God, I want to.
 
FUCKING
My wife had an affair with her college boyfriend 15 years ago. When she finally admitted it, I was hurt and angry. I thought about filing for divorce, but because we still had a child at home, I didn't. I did move into the guest room and we went into counseling, but I had no interest in a physical relationship. Then, one weekend afternoon, about 4 months later, she was in the kitchen. I came up behind her and spun her around, kissing her and cupping her ass. I dragged her into the living room and pushed her down on the couch and mounted her. We were frantically pulling each other's clothes off. I plunged my cock deep into her cunt and fucked her like an animal, all my hatred, anger and depression channeling though with every thrust. She was biting my neck and shoulders and and digging her nails into my arms and back, even drawing blood. No words were spoken. I finally came, pumping my load deep into her and collapsed on top of her, both of us covered in sweat. We stayed together, but the sex as never been as hot it was that afternoon and for the next few months.

HANDJOB
I know the post asked for the best oral orgasm. Unfortunately, I've never been in a relationship with a woman who particularly enjoyed oral sex. I've had my share of blowjobs, but only as foreplay. But I do recall one amazing handjob. (AND YES, MR. MODERATOR, BOTH THE GIRL AND I WERE OVER 18 WHEN THIS HAPPENED). It was my senior year. I had a respectable girlfriend at school, but I also had a "church girlfriend." Every Sunday and Wednesday night, after services, I would drive to the lake outside our small town and we would makeout like the horny teenagers we were. These sessions involved a lot of dry humping, fingerfucking, pussy eating and handjobs. Normally, I would go down on her, get her off, and she would return the favor with a handjob in the front or back seat of my 1969 Pontiac Bonneville. She would take my cock in her hand, stroke me to orgasm, then grab a tissue out of purse and clean up the mess. One night, she deviated from this routine. We made out, then I knelt on the floorboard, pulled down her pantyhose and panties far enough to go down on her and tongue her clit and finger fuck her. After she came, I crawled up on the seat next to her, expecting the usual handjob. This time, though, instead of roughly jerking my cock she placed it on her thigh and began rubbing it up and down her pantyhosed thigh. The sensation of my cock on the nylon and occasionally on her fleshy upper thigh was mindblowing. I shot my load on her leg and belly. Instead of retreiving a tissue, though, she scooped up the jizz and rubbed it into her breasts, then sucked her fingers and said "Yum." It was, at that time (and frankly still is) the sexiest thing I've ever seen. I have no idea where a girl in the sticks in West Texas in 1974 got the idea to do that...By the way, if you've looked at my posts in other forums, you know I have a pantyhose fetish. Do you wonder why?

MASTURBATION
Fast forward 25 or 30 years. I considered myself 100% heterosexual. I don't recall ever feeling attracted to men until one day when I went to pick up my daughter and her friend at a local swimming pool. I walked toward the pool and two college-age life guards were walking past me. Smooth, muscular bodies, six packs, bronze skin, water from the pool clinging to their bodies, dripping down the front of their trunks to the thighs. I collected the girls and dropped the friend at her house. As soon as we got home, I told my daughter I wasn't feeling well. I locked the bedroom door, stripped and laid down, my head at the foot of the bed, my feet in the air, braced agains the headboard. My cock was rock hard. I fantasized about being on my knees, licking and kissing and sucking my way down those gorgeous bodies to those hot, young cock. It didn't take long. My back arched and the first spurt went over my shoulder and some of it hit my cheek and neck. The second spurt hit me in the chest and the poured out of my hole and ran down my shaft, pooling at the base of cock. So fucking good. I still haven't sucked a cock, but God, I want to.
Awesome stories, thanks
 
FUCKING
My wife had an affair with her college boyfriend 15 years ago. When she finally admitted it, I was hurt and angry. I thought about filing for divorce, but because we still had a child at home, I didn't. I did move into the guest room and we went into counseling, but I had no interest in a physical relationship. Then, one weekend afternoon, about 4 months later, she was in the kitchen. I came up behind her and spun her around, kissing her and cupping her ass. I dragged her into the living room and pushed her down on the couch and mounted her. We were frantically pulling each other's clothes off. I plunged my cock deep into her cunt and fucked her like an animal, all my hatred, anger and depression channeling though with every thrust. She was biting my neck and shoulders and and digging her nails into my arms and back, even drawing blood. No words were spoken. I finally came, pumping my load deep into her and collapsed on top of her, both of us covered in sweat. We stayed together, but the sex as never been as hot it was that afternoon and for the next few months.

HANDJOB
I know the post asked for the best oral orgasm. Unfortunately, I've never been in a relationship with a woman who particularly enjoyed oral sex. I've had my share of blowjobs, but only as foreplay. But I do recall one amazing handjob. (AND YES, MR. MODERATOR, BOTH THE GIRL AND I WERE OVER 18 WHEN THIS HAPPENED). It was my senior year. I had a respectable girlfriend at school, but I also had a "church girlfriend." Every Sunday and Wednesday night, after services, I would drive to the lake outside our small town and we would makeout like the horny teenagers we were. These sessions involved a lot of dry humping, fingerfucking, pussy eating and handjobs. Normally, I would go down on her, get her off, and she would return the favor with a handjob in the front or back seat of my 1969 Pontiac Bonneville. She would take my cock in her hand, stroke me to orgasm, then grab a tissue out of purse and clean up the mess. One night, she deviated from this routine. We made out, then I knelt on the floorboard, pulled down her pantyhose and panties far enough to go down on her and tongue her clit and finger fuck her. After she came, I crawled up on the seat next to her, expecting the usual handjob. This time, though, instead of roughly jerking my cock she placed it on her thigh and began rubbing it up and down her pantyhosed thigh. The sensation of my cock on the nylon and occasionally on her fleshy upper thigh was mindblowing. I shot my load on her leg and belly. Instead of retreiving a tissue, though, she scooped up the jizz and rubbed it into her breasts, then sucked her fingers and said "Yum." It was, at that time (and frankly still is) the sexiest thing I've ever seen. I have no idea where a girl in the sticks in West Texas in 1974 got the idea to do that...By the way, if you've looked at my posts in other forums, you know I have a pantyhose fetish. Do you wonder why?

MASTURBATION
Fast forward 25 or 30 years. I considered myself 100% heterosexual. I don't recall ever feeling attracted to men until one day when I went to pick up my daughter and her friend at a local swimming pool. I walked toward the pool and two college-age life guards were walking past me. Smooth, muscular bodies, six packs, bronze skin, water from the pool clinging to their bodies, dripping down the front of their trunks to the thighs. I collected the girls and dropped the friend at her house. As soon as we got home, I told my daughter I wasn't feeling well. I locked the bedroom door, stripped and laid down, my head at the foot of the bed, my feet in the air, braced agains the headboard. My cock was rock hard. I fantasized about being on my knees, licking and kissing and sucking my way down those gorgeous bodies to those hot, young cock. It didn't take long. My back arched and the first spurt went over my shoulder and some of it hit my cheek and neck. The second spurt hit me in the chest and the poured out of my hole and ran down my shaft, pooling at the base of cock. So fucking good. I still haven't sucked a cock, but God, I want to.
I can definitely relate to your first story. You are angry and jealous but you want her more than ever and sexual attraction becomes paramount and you become very horny!
 
1st one: living in a small town before the Internet, I had never heard about orgasms until after I had my first one. One of the older boys worked his magic and made fun making out to, very intense and addictive making out. But the feelings of that first one will never be forgotten.

2nd: first gspot orgasm, pretty sure it was totally by accident on the part of my partner but it felt magical never the less.

3d: actually on lit chat, during a very intense rpg, what made it special is because it was without active stimulation, just hours of cerebral excitement and legs rubbing together, had it happen several times over the years, but the first one, not knowing I could get off without some manual labour was mind blowing
 
1. Cumming while my wife was removing her fist from my ass.
2. First time I was on top for anal. We were both anal virgins.
3. Fiinally cumming after edging for nearly an hour and a half.
 
My best from fucking? The first time I shot in her pussy after a year of pulling out. LOL

From oral? Her sucking me when on a late night journey with several family members asleep in the back of the van.

From masturbating? A tie. One time jacking off while nude at night in an open field with a gentle warm, rain falling. The other time, after she told me in detail about her grandfather eating her pussy to orgasm after fucking her. Tie goes to the grandfather story. Very intense...
 
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I have had a number of memorable orgasms over the years and all of the best ones were from fucking. Masturbation was always just for relief and oral is OK but I really like to feel a cock inside of me when I cum. One of my memorable ones was at a hotel in Boston. My husband was supposed to join me Friday night but postponed until Sat morning. I was a bit pissed but also very horny. Met a guy at the hotel bar, decided to let him walk me to my room, decided it would be OK to make out for a bit before I sent him on his way. Decided I would suck him off and then send him on his way. He wanted more and while my mind said no, my body said yes. Of course neither of us had condoms and I was too aroused to send him away. Thought about asking him to pull out but then forgot about it when I was heading for a real nice orgasm. Remembered it again when I felt his cock pulsing inside of me. After that first pulse, there was no reason to worry about it. A million sperm were having a race inside of me so what difference would a few million more make. Plus I had a really intense orgasm while he was fucking me so I used the same logic the next morning when I let him fuck me again.
 
Tough picking one of each, I’ve been around more than a few years but these pop into my head.

Masturbating...Listening to the audio recording of my wife with a man who was our first when we tried swinging. Extra large cock, sure didn’t sound like her.

Oral sex. The first time my wife did oral sex with me, a couple weeks after I met her. I warned her I was about to come and she looked up at me and said I want you to cum in my mouth. I forced myself and watched as she looked me in the eye while she swallowed my whole load.

Fucking. The first time I fucked my friends wife. Unexpected but when she climbed on me I had all I could do not to cum quickly. God can she move..

Honorable mention.
Masturbating....coming with out touching myself, little excited listening to my wife and friend when I was blindfolded.
Oral....Have 3 girls, one my wife, sucking me one after one, think around the world.
Fucking......First time I fucked my wife. Only took once I married her 6 months later
 
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