My valentine gave me multiple orgasms amongst other things for the first time. [FM]

Hi everyone!

Update. Story time. Confession. Was suggested to post here since it’s a lot of text?

Sorry for the inactivity and not responding to messages, comments. Kind of forgot I had this and with school and hockey I’ve been swamped.

Okay, to answer your questions about Scott, no I haven’t joined or hooked up with him. Scott and Kels’ fling fizzled out and he hasn’t been over for a couple weeks. I was too much of a scaredy cat to do anything or take him up on the offer, I told Kels about it after and she laughed saying that I should have joined and reiterated the fact that I missed out. She wasn’t upset or anything, honestly she’s so drop dead gorgeous she can get any guy she wants so it’s on to the next one for her.

Well a couple weeks ago I run into Scott who’s training another hot older guy at the gym, I’m introduced to Caleb and get serious Daddy/Silver-fox vibes from him. He’s fit, salt and pepper hair, about a foot taller than me with a great ass. His killer blue eyes and dimples did it for me and I had no problem for the rest of my workout catching the two checking me out. I learn he’s rehabbing his knee that he blew out from hockey *ding ding* and he’s friends with Scott’s older brother.

Fast forward a couple days, he finds me on the gram and we flirt back and forth. I’m flattered but the age gap is pretty significant, Caleb is 29 and already divorced. Ya I know, he’s almost a decade older but fuck he’s hot, like stupidly hot. Plus he’s really sweet and our conversations never go dry, I love seeing his name pop up on my phone. I know it’s kind of wrong but that doesn’t stop us working out a couple times a week, full on flirting and getting handsy with each other in between our lifts. Like I said, he’s got a huge booty which is kind of my thing so we exchange motivational butt slaps before every set and I’m sure it looks like we’re dating. We joked that watching each other lift was our kind of foreplay, hands would often wander when there’s no one around. We kept it PG for a couple days which was getting increasingly difficult.

So I don’t know how long these things can get but in an effort to get to the “Juicy stuff” and be reader friendly we made plans for valentines day. He has to work 12 hours and I have a team workout after class so we agree to meet up for a drink at his condo. There was no question what was going to happen that night, our gym antics and sexting leading up to vday had us in the mood. I fucking needed this, needed him BADLY. A shot of tequila and glass of wine was finished in probably 5 minutes, then he had me in his arms while we made out and our hands wandered without concerns of others.

As we kissed he somehow had the straps of my dress already down my arms and as he licked my neck he pulled the dress off me, fuck that was hot. He whispered into my ear how much he loved my body and asked if I could sit on his face, until that point no one had ever asked that. Thank god I was freshly showered and practically willing to do whatever he wanted with how turned on I was, so I said yes and he walked me into his bedroom.

We kissed a lot more and I helped undress him which was another first for me, the entire night was pure passion. Something a lot of 20 year olds aren’t doing and should take notes from older guys is it’s a marathon not a sprint. When he finally got his jeans off I rubbed his hard cock through his compression underwear, I’m not going to lie to you and say he was this massive porn star cock but he was still a bit bigger than my ex who was perfectly average. Which I’m seriously grateful for because those huge ones like Scott’s are scary.

What I did enjoy was how as I got on my knees to give him head his dick sprung out of his undies and I saw how pretty it was. He was groomed and smelled wonderful, I think I showed how appreciative I was as I took him into my mouth slowly and he stared at the ceiling letting out a long “holy shit”. Using lots of tongue on the underside of his head, coating it before I deepthroated him. As I retracted his cock from my mouth our eyes met and he looked at me with that cute smile and said I was amazing, I loved hearing that. It was a new feeling for me to be so turned on while giving head, I could get used to this.

Then he told me he wanted to taste me, I really loved hearing that.

He laid down on his back and told me to sit on his face, as I squatted down for the first time on a mans lips I braced myself with his headboard. He knew exactly what he was doing, it’s hard to explain but it was as if he was tongue kissing and tongue fucking my ass before giving my pussy the attention she wanted. When his mouth met my clit I could tell I was close to cumming, another first for me. I’ve never orgasmed from oral or penetration. Unfortunately I couldn’t get to the finish line, not in this position. It got too uncomfortable for my legs so I begged him to fuck me, no exaggerating I really was begging.

Caleb bent me over and he teased me for what felt like eternity with his cock, rubbing it against my lips and clit before sliding in only a few inches and pulling it back out. At one point the teasing was too much and I backed my ass against him and felt that addicting feeling of fullness for the first time, it was breathtaking. It had been too long since I’ve had a penis inside me and you can guess how quick it was until I came. Spoiler: It wasn’t long.

He quickly learned and was responsive to everything I liked, something I’ve never had before. While most boyfriends or hookups just jackhammered me until they finished, Caleb had this perfect harmony of slowly increasing his thrusts and the tempo.

In doggy I could feel myself gripping his cock while he held me by my hips and controls the pace, slow at first then steadily accelerating his thrusts until he’s pounding me. I can feel tingles flow through my body and my temples pulsating as I’m about to hit my first orgasm from sex ever.

This is when every man I’ve ever been with usually finishes but Caleb keeps going and each thrust is literally taking my breath away. My body begins to get red hot and in between my uncontrollable moaning I scorn Caleb and tell him don’t stop, he doesn’t and he somehow fucks me even harder while grabbing a fistful of my hair and instantly I full on scream. My vision narrows and I have a full on out of body experience, I’m finally orgasming. I lost the ability to hold myself up on my forearms and Caleb eases up but never stops fucking me, I’m making noises i’ve never made or knew I could produce. Another wave of pleasure hits me and he penetrates me through another orgasm, this one causes my body to convulse as I’m overdosing on endorphins and he leaves his dick buried inside me as I come back to earth.

At this point I’m lightheaded, somewhat numb from the overwhelming sensations and this amazing man knew that my body needed a cool down as he traced his fingers along my back and ass while still inside me. After a few minutes he pulled out and I lay there lifeless in his bed, we laugh and I have to embarrassingly admit that it was my first orgasm with someone else. It doesn’t phase him at all and he promises that it won’t be the last tonight.

I’m ready for round 2 as we lay on our sides and begin kissing again, Caleb’s runs his fingers all over my skin and eventually between my legs. He fingers me and expertly finds my G-spot while circling my clit with his thumb, that electricity once again jolts through my body but all of a sudden he stops. Pulls his fingers out of me and tastes them, then he puts them in my mouth and says look how good you taste. FUCK FUCK FUCK that was hot. All I could muster up was “I need you to fuck me” which he had no reservations with.

Now I’ve had missionary sex before, most of us have and traditionally for me it’s been bland. What Caleb did was anything but. It was a combination of making love, fucking and a full on assault of my vagina. He laid on top of me with his weight pinning me down, forearms beside my shoulders and kissed me as he slid inside. I took the opportunity to squeeze his muscular butt as he moved his hips in circles, being able to pull him close and feel him squeeze his glutes was addicting. But soon those thrusts were more straight on and powerful, I was beginning to feel like I was going to explode again and dug my nails into his skin. His strength was something I’ve never felt before and I wrapped my arms and legs around him holding on for dear life while he fucked me stupid.

I could feel my face and chest getting flush then for whatever reason I was biting his shoulders, neck, whatever was close in between whimpering and moaning. Finally that first wave of euphoria hit me and I had to close my eyes as what felt like every muscle in my body tensed up, I couldn’t even moan any more. My brain smoothed over and I lost all my motor functions, I felt like I was melting then my body went limp. When I regained consciousness a second later I began screaming and shaking underneath him. I fucking literally passed out from orgasming so hard, it was unreal! And something I yearn for constantly now.

This has gone on too long, I’m sorry if I lost you Reddit. Caleb and I spent the night having more sex, taking breaks to hydrate, hang out and cuddle. I won’t say I’m ruling out younger boys but my first experience with a man who clearly appreciates a woman’s body is something else. Thanks for reading and I hope you cum as hard as I did.

Source: reddit.com/r/gonewildstories/comments/swrkpj/my_valentine_gave_me_multiple_orgasms_amongst