Most memorable orgasm

It’s a really long story but basically I ended up in a situation where my cousin shared his much older fuck buddy with me back in college. She was a thick puerto rican woman with a big personality, old enough to be both our moms and even had grandkids. Despite her age, she had a young spirit and an absolutely amazing body. She came over one night while I was hanging out with my cousin and after we all got drunk together, we both ended up fucking her all over the apartment. The wild part for me was that she was married and despite just meeting me that night allowed me to fuck her unprotected and cum in her a couple times.

Even though I came in her mouth earlier that night (which felt great) the “big one” occurred at the very end of our romp. Without going into all the details, I ended up in her ass while we were spitroasting her on the couch and only lasted a couple minutes before blowing up huge load that damn near filled up her rectum. The orgasm itself lasted longer than usual and it felt so good that I got blurry vision for a moment and my legs got really weak. The actual physical stimulation was amazing because she had a big, jiggly ass that was incredibly soft and her anus wasn’t super tight and well lubed. On top of that, the mental stimulation of the situation itself took everything over the top so when it all hit me at once, I just exploded.

Alotta little details I left out but that’s the gist of it.

 

only one was and that was wild to say the least!

 

My first anal orgasm

 

Care to share a few details?

 

It was over nine years after my first orgasm before I experienced sexual intercourse at age 22. My first orgasm inside a vagina was so intense it nearly blew my brains out, and I gave a loud involuntary cry. That first time I looked at my girlfriend’s genitals and had no idea what I was looking at – she pointed out her clitoris though I wasn’t sure I would be able to find it later. She guided my penis in because I didn’t know exactly where the vagina was. Until that night I had no idea that females use their fingers to stimulate their clitoris during intercourse.

I have had lots of orgasms, but some are very memorable:
- My first masturbation, first wet dream, and first sexual intercourse.
- In my early teens, late at night I sneaked into the living room, lay on the couch, and masturbated. The ejaculation flew right over my head and landed on a table nearby.
- On a touring holiday with my wife, I felt horny most of the afternoon and had my hand down my pants at every opportunity (e.g., while walking a trail). When we had sex that evening, I was highly aroused, and my wife was well in the mood too, so it was mutually satisfying. My plateau was long and delicious and built to a breathtakingly pleasurable orgasm.
- On a week-long car trip by myself I called into an adult store and bought a sex magazine (the only time I have ever done such a thing). I sneaked looks at it during stops on my journey and was horny all afternoon. I checked into my motel in the evening and quickly got naked. I lay on the bed masturbating for two or three hours while looking at the magazine, eventually letting myself go. The orgasm was intense, the hole in my penis opened wide and big shots of semen flew out.
- When I masturbate in bed with my wife asleep next to me, I need to do it quietly and slowly to avoid waking her. I remember the first time - the plateau seemed to go for ever, building gradually to the eventual explosive orgasm. I sometimes experience a delicious plateau like a nice tickle with a feather along the inside of the urethra.
- One time I watched internet porn for hours. I was touching my penis most of the time, nearly getting to orgasm several times. When I did let myself go, I kept rubbing and there was lots of spurts and volume. The semen was white and wet, with a pungent and pleasant smell that filled the room (more so than normal).

 

My most memorable happened with a dominatrix giving me an intense electro session. I had one sticky pad electrode on my dick, with a bipolar electrode up my ass and she used a TENS device to tease me to a hands free orgasm while I was in four point restraints tied to a bed. While I was ejaculating she turned the power on the TENS unit all the way up then held a vibrator on the tip of my dick. The result could only be described as an inescapable blend of agony and ecstasy which seemed to take forever forever to subside. She caught as much of my cum in her hand as she could and force-fed my cum back to me all the while with the TENS unit zapping me.
It was both the most humiliating and intense orgasm I had ever experienced.

 

I was standing naked in the living room of my girlfriends apartment afraid her roommate would come home with friends.
My hands tied behind my back as she stroked my cock. She brought me close to orgasm five times but didn't let me cum.
The last time a single spurt of semen popped out and she laughed hysterically. By then I hoped her roommate would come home, maybe she would end this torture and let cum.
Finally she relented and slipped a well lubed finger in my ass as I came. We went to her room and minutes later her roommate arrived with friends.
This seems to have led to a fascination with being caught.

 

As well as it being someone who respects her and her needs.

 

There isn't really one that is most memorable. I'll recall one and then another which is more exciting and then another and it depends on how I am feeling as to which seems the best. Anyway, there is one that always is good to remember.
My fb of the time worked in a cake shop. I was to pick her up at the end of the day and so when I walked in, I was directed by the till operator, to the back of the shop, into the prep room. There was my fb, in 4inch heels, a short denim skirt and a white vest top. No bra and her small breasts were sitting there looking lovely with her raspberry sized nipples poking out. No visual of them, the top was too think but the shape was there and quite erotic. I walked towards her, where she was leaning on the worktop and writing in an open file. I stood beside her and ran my fingers around her thin waist. She seemed not to respond so I traced my fingers over her bum and down to her knees, before running them up the insde of her thighs to where she had no underwear. She was already wet and then she responded by saying she had been stroking as she waited for me. I stroked her a little before she squeezed my trousers and told me to 'come here'. She took me by the hand and walked me into the utility room beside the prep room, where the utensils and dishes were cleaned. The instant we were there, she crouched to her knees and opened my trousers, releasing my semi-hard cock. She slid her mouth over it and started to suck. She loved my cum. I know that because she worked me off twice a day with just her mouth and actual sex was a seldom thing. I became fully erect and she licked me up the whole of my length before putting me into her mouth again. She was very good at it!
I stood as she continued to suck and I was feeling the buildup begin. She continued to suck me whilst at the same time, she reached around her body to grab her top and to pull it off. A short pause in sucking as she pulled her top over her head and then she resumed. I had lost some of the buildup as she did that but it was OK. I looked down to see her pert breasts and delicious nipples and noticed she was opening her skirt. She raised her body enough to remove it without missing a beat on my cock and then, naked but for her high heels, she continued to suck and she stroked herself. I couldn't see that properly but I saw her arm moving which made it clear to me what she as doing. I wanted to watch and she knew that from a previous conversation. She undid my trousers fully and puled them and my shorts down to my ankles. It was a warm summer's day and very sunny and as she pulled down my trousers she noticed I had removed all my hair. To me, my cock looked much bigger without the hair and she just said Wow, before sucking me again. Then she licked my scrotum and behind it and then wrapped her hand around it as she took me into her mouth again. If she kept going I was close to cumming but she stood up fully and caressed my cock with her hand as she kissed my lips and slid her tongue around to suck my ear lobe. And then she stroked her tongue around my face to my lips where she sucked my tongue with her mouth and squeezed my cock again. She whispered in my ear to fuck her right now and she leaned over the counter again spreading her legs so her feet were about 3 feet apart. She pulled open her cheeks and told me to put him in.

Who am I to argue?!

She ran her own fingers around her lips and clitoris basically masturbating herself when, just as I was about to enter her, the till operator (who was a friend of hers), came down saying she had finished as was going home. She put her head around the door and saw my fb masturbating and my hard cock sticking out proudly and moving towards her lips. My FB responded to her friend with OK but didn't turn around. I was in too much of need to stop so I entered her about 1/3 way in and then out to the edge and then in again, repeating that for a couple of minutes until I heard a definite breathing change from my FB and then she came. I kept thrusting gently until she moved and I fell out. She turned around and noticed her friend standing there. I had forgotten about her. She (my FB) said it was OK, that they had seen each other cumming and fucking before and then she asked the other one what she would like. I was now stroking myself to avoid losing my buildup and the other one removed her apron and then her T-shirt and bra. My fb pulled down her jeans and panties to reveal a very smooth-looking vulva. Her body was lovely. Her breasts were probably a good B cup, firm-looking and rounded with little but quite dark and appealing nipples. Now I was standing hard, with two lovely women naked in front of me. I suddenly panicked and asked if she had closed up the front of the shop. She hadn't and ran naked to the door to lock it. I took off the rest of my clothes so we were all naked and still stroking, I asked my fb what she would like to happen. She said not to worry, that I would enjoy it.
The other one came back and they both knelt in front of me, with my fb licking my shaft and the other one taking me into her mouth. I'd never been in this situation before and was amazed, excited and unsure, all at the same time. What really was going on, I wondered.

They kept sucking and licking me, changing roles and soon, I was going to erupt. My fb took it all and savoured it as usual whilst the other then sucked a little leakage from the tip of my cock. They kissed and shared my cum. I had not seen such passionate kissing between two women, even online and it was mind-blowing. I kept stroking gently and was picking up drops from my tip as they continued to kiss and then I noticed they were fingering each other. And then my fb lay on the counter whilst the other went down on her. I was getting hard again and watching them was absolutely lovely. I moved towards the other one and stroked her cheeks with my cock, as I moved him closer to her opening. I stroked her moist lips with my knob but then, without breaking away from licking my fb, she took hold of my cock and held me and squeezed me, without sliding up and down my shaft. My fb came. It was very intense, more intense than I had helped her to achieve before, which disappointed me slightly.

They swapped positions without her letting go of my cock and so we ended up with she on her back with my fb licking her and she sucking my cock. God, she knew how to suck hard and for a prolonged period. Very shortly afterwards, I really needed to cum but it wasn't happening yet. I felt as I normally do (though more intensely) just before I cum but I wasn't moving closer to that orgasm. I was beginning to tremble and my breathing changed to a holding of breath followed by panting, before holding it again. My body was rigid from head to to and I was standing on my tip-toes desperate to cum. Still, nothing more, just me on the edge desperate to cum and unable even to look at her and to enjoy watching her sucking me.

Suddenly I could feel it. I was building up more and more and I knew I was gong to cum. I counted back, 5,4,3,2,1 but nope, no orgasm. (Is it just me that does that sometimes?). And then again but as I began the countdown BANG!
I was shaking, pumping, moaning and spurting into her mouth and I could feel her, still licking me round and around my knob. My orgasm subsided. I was feeling amazing and the woman opened her mouth and pointed at my cum. She beckoned my fb, whom I had forgotten about, down to kiss her and they shared my cum before they both swallowed some of it. I kissed her too whilst my fb went down on my to lick up any more cum. God she was a good kisser.

I stepped back to gather myself. It was the most mind-blowing orgasm I had had up to that point in my life. My fb went down on her friend again and I just marvelled in the delight of watching two beautiful women, totally at ease with their sexuality, giving each other an orgasm.

It's a day I shall never forget and whilst we did a repeat at my FBs place, that first time was the best.

 

It was the first time at a glory hole. Having my pants down around my ankles and being pressed up against the wall while my dick and balls were being serviced by a stranger on the other side was incredible. I didn’t think I would ever stop cumming. Years later, I was at another GH and had a similar experience. Just kept cumming and cumming

 

The first time I orgasmed from prostate stimulation. The cum just started flowing out of my cock like a fountain.

 

I was with a cougar (she was 40 I was 24) when she got on her knees and started sucking on my Dick. She didn’t even try and deep throat me (only one gal could) but made love to the fat head (is wrist thick). Whatever she did I came like I never had before or since. I clutched at her head as blew my load. I had to sit down afterwards and I had know that of my dick had blown into her throat. I looked puzzled at her now knowing where my cum went. She smiled at me licked her lips and told me it was delicious. Best blow job ever.

 

For my wife, it was the first time she was made to squirt. My multi-orgasmic wife request that she’s given a chance to recover after she’s orgasmed. She was with a guy that totally ignored that rule. He had her bent over the end of the bed and at his mercy. When she orgasmed he started fucking her very harder. Suddenly, she stopped screaming and stared at me as if something was wrong. I started to put a stop to it until I could heard a squirting noise. She just stared at me with her eyes and mouth wide open as she loudly squirted every time he thrust into her. When he finally stopped she had body convulsions for another minute. The bed sheets and the ground beneath her was very wet. My wife thoroughly enjoyed it but she said she was confused with what was happening. She had no control over what has coming out of her body. It was her most memorable orgasm.

 

For me the best experience is being in missionary position going bare with a pillow under her butt to give a good angle for deep penetration and then to have her lift her legs up high to really offer up her vagina..

The thrusting should be slow at first and sensual, lots of eye contact.. Then build up slowly to a faster pace.. Be very present, meditative..

What I really enjoy is when I lose control, when the feeling gets so intense my body just takes over, and it goes from making love to "I need to deposit cum inside this woman!" Then those final thrusts, that last one that is involuntary, when every instinct makes me push the dick in as deep as it goes, and she right at that moment closes her legs around and pulls me close.. She locks me in and helps insure that the semen goes well into her..

That is the kind of orgasm that is magical to me and makes me feel fully and completely accepted.

 

Short version... probably during our first threesome with my wife and a buddy ! Lots more to the story . One of the best nights of my life .

 

It must be fucking my ex girlfriend's mother she wanted it badly she was so thrilled in her words to be fucked by a young stallion. I eventually cum in that great ass.

 

Mine was the first time fucking a girlfriend raw and cumming inside her! We had had sex twice before with condoms. This third time, at her place, she was topless, straddled on top of me with just her panties on, getting them wet grinding on my hard cock.
She pulled her panties to the side to feel my cock, wet with precum, slide against her wet lips as she grinded on me. She said would you like to feel it inside me without a condom? I said yes! She said I'm in the pill,but if I have a baby, I'm keeping it, and are you ok with that? I told her I'd be hers forever if she had my baby!
She stood up, shimmied her panties off, kneeled down, rubbed my cock head against her opening, moaning, saying I want you inside me, I want to feel your warm cock and cum fill me up!

I had other girls who wanted me in them raw,disappointed I wouldn't, but she was the first girl I truly didn't mind if she got pregnant, as she was beautiful, with gorgeous eyes that could flash you a look, bi, and a great sex drive drive and incredible sexual chemistry!

When I first slid inside her, the sensation was like the Wizard of Oz, going from black and white to vivid technicolor! Sex before was kind of bland and dull with condoms, and I felt more stimulation from kissing and making out. I couldn't really cum from uncovered oral for some reason, either (still difficult)? I honestly did not know what all the fuss about sex was other than the woman getting naked and feeling her skin?
But man alive, sliding in her wet, warm snug pussy without a condom on for the first time in my life was just incredible! so many sensations I'd never felt before from masturbating, oral, it condom covered sex were overloading my mind as I watched her riding up and down and grind her hips back and forth into me, pressing her clit into my pelvis!
This went on for about 9 minutes, then I could feel the point of no return coming near. I told her I was close, and she moaned give me your cum, I want it in me! And that did the trick, and I had the best orgasm of my life inside of her, and then she came fingering her clit., still in top of me, grinding away as my huge load of cum started leaking down onto me. Her cheeks got flush, I could feel her muscles quiver on my still hard cock, then clamp down on my and she rolled her eyes back and moaned as she came while I was I side her, then collapsed onto me, kissing me with her still flushed, warm cheeks against mine!

I still masturbate to that night now and then, 22 years later (I was a late bloomer, she was my first true serious girlfriend). I only wish I would have said yes to her wanting a bi three-way with her girlfriend(s) early on! I told her not for awhile, as I wanted to focus on us first, and then would try it with her.

 

Working in a hospital early 80's, started an affair with a married, but both of them considering divorcing, laboratory technologist. She'd miscarried twice and that's why they were thinking about separating. Our time lasted about six weeks and we fucked beautifully about five times. I was single and seeing her every day at work I fell completely in love with her.

Well, she got pregnant. But by her husband. We talked and she'd counted very carefully and it wasn't mine by about four or five days, and they'd reconciled and were going to make it work. She knew it broke my heart. But we both knew it had to be.

When she was about four months along, one weekend she came to my house. We talked and wound up lying next to each other. She slid down, took me out and began to do some of her wonderful mouth work. As I got closer, she stopped, looked me in the eyes, and said, "At least this little one growing inside me will now have a part of you."

That was the most intimate thing I've ever heard. Forty-two years later I remember every moment of it.

 

who could forget that