The story of my [M] first real sexual experience of my life at 19, losing my virginity to a MILF, and cumming 5 times in one night

**(This very long post so TL;DR: Met a woman in her 40s when I was 19 and was a virgin who had only kissed occasionally and touched breasts a single time. Got coached by her, came from a lap dance, lost my virginity, and came more times in one night than I ever have in a single night since then.)**

•I had a lot of fun writing out my last experience and interacting with the comments, so I decided I’d write out another post. I will probably write more stories detailing each of my significant sexual experiences in over time.

•I know my posts are very long, but I like to give as much detail as possible. Since this experience was 7 years ago some details may still be left out. I tried to include everything that I remember in detail.

**I apologize for any typos or formatting errors. I tried to make it as readable as possible. I’ll edit the post and correct it if I find any errors.

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I didn’t lose my virginity until I was 19. Most of my life I was really shy and quiet, so I never really tried to find relationships or hookups until then. One day I was on the dating site MeetMe and started talking to a woman who was in her 40s. We talked for a few days until the conversation turned spicy. We started sexting, and kept flirting and sending each other nudes for about a week. At one point I told her that I was a virgin and she seemed very intrigued by that. Then one day she asked if I wanted to come to her house sometime and of course I said yes. She had a teenage daughter though so we had to wait for a day that she wasn’t there. We kept talking for a few days until she finally told me that her daughter was spending the night at a friends house and that I could come tonight if I wanted.

I was so damn nervous that I almost said no from the anxiety of it all, but I told her I would be there. She gave me the address and it ended up being about a half hour away, so I took a shower, got in my car, and drove there with my heart pounding away during the entire drive.

I arrived at her house at around 8pm. It was a nice house in a suburban neighborhood. I texted her that I was there and she told me to come to the door and she’d let me inside. I stood at the door for a minute or two until I finally heard the lock turn and the door opened.

When I first saw her I couldn’t believe how beautiful she was. She had long blonde hair that went over her shoulders and she was wearing a red tanktop with a black bra that peeked over the top of her shirt. She was wearing long black yoga pants that hugged her legs tightly. She smiled at me and told me to come inside. I walked through the door and she closed it behind her.

We went over to the couch and sat down next to each other, sitting a few feet apart. She was sitting on the couch with her legs up facing toward me with her arms wrapped around her knees. We made some small talk for a while and eventually she said, “you seem nervous”. I replied, “yeah, I kind of am.” (The dialogue parts of this story might not be the exact wording that was said but I recalled it to the best of my memory. I’m sure there is plenty that was said that I don’t remember)

•**Her** “So you’re a virgin, huh?”

•*Me* “Yeah.”

•**Her** “So what have you done? With a girl, I mean.”

•*Me* “I’ve had a few girlfriends who’ve I kissed, and I’ve grabbed a girls boobs on a dare at my friends birthday party one time. That’s about it though honestly.”

•**Her** *giggling and smirking at me* “Wow, so thats it then?” – *she paused for a few seconds* – “Do you want to change that tonight then?”

•*Me* “Um… yeah, if you want then of course.”

She scooted closer to me on the couch, putting her legs down and criss crossing them beneath her.

•**Her** “I have a fun idea, lets start slow and work our way up. Touch my tits, over my shirt for now. Go on.”

I reached out my hand and placed it onto her right breast, sqeezing it gently for a few seconds. Then I moved over to her other breast and did the same thing. I felt her breasts for about 30 seconds. I’m not sure what her cup size was but I’d guess around a C cup, not small but not huge. They felt great, but most of the squeezing was just a handful of her bra cups.

I pulled my hand back and she quickly uncrossed her legs and leaned over me, pressing her lips to mine and kissing me. She slid her tongue through my lips and intertwined it with me. We made out for about 15 seconds before she pulled away and spoke.

•**Her** “So, that’s everything you’ve done then?”

•*Me* “Yeah. That’s everything.”

•**Her** “Well you kiss really well, I’m surprised it never went any further with any of thise girlfriends you’ve had.”

•*Me* “It probably could have but I was always too nervous to try and make any moves.”

•**Her** “Don’t be nervous about it tonight, but let me guide you okay? Come on, lets go into my bedroom. This couch is too cramped.”

We stood up and I followed her into the bedroom. She laid down on her stomach on the bed. I sat in the edge of the bed next to her.

•**Her** “Rub my butt now, over my pants for now too”

I turned toward her and placed one hand on her butt, running my hand along the curves of her firm ass while squeezing and massaging her cheeks. I took my other hand and placed it on her other cheek, doing the same with both hands for about 2 minutes or so.

•**Her** “Now, pull my pants down, but just over the edge of my butt okay? Then do the same thing you were just doing.”

I grabbed each side of her waistband at her hips and pulled her pants down just enough to expose her bare ass. Then I rubbed and massaged both of her cheeks just as I had before. At one point I gripped them both and pulled them apart just enough to see her asshole. I was rock hard by this point. She made some soft, quiet little moans as I massaged her. This continued for a few minutes until she told me to pull her pants back up, which I did.

She then sat up on the bed and pulled her shirt off over her head, tossing it onto the floor. She followed that by unclasping her bra and tossing it aside as well, leaving her completely topless so I could see her bare breasts. She had large brown areolas and thick nipples. She looked incredible.

•**Her** “Now touch my tits again, and then you can suck on my nipples.”

I moved over to her and cupped my hand around her left tit, feeling my first pair of bare breasts ever. I ran my fingertips across her nipple and lightly pinched it and rolled it between my fingers before moving to the other tit and doing the same. Afterward, I ducked my head down and took one of her nipples into my mouth. I wrapped my left hand around her and placed my hand on her back to keep myself steady. I flicked my tongue over her nipple and sucked on it for probably 3 whole minutes. About halfway through she put her hand on the back of my head and started running her fingers through my hair. Eventually she spoke again.

•**Her** “Okay now stop.” *I stopped and she lied down on her back.* “Now touch me between my legs”

She spread her legs apart and I reachedown there, still with her tight pants on. I rubbed her inner thigh for a moment. I could feel warmth radiating from between her thighs. I moved my hand inward untilit was placed on her pussy. I rubbed my hand around the area and could feel her pussy lips moving around beneath my fingertips. I rubbed her for a few minutes before she spoke again.

•**Her** “Okay now stop.” *she sat up* “Now you lie down.”

I lay down on the bed and she sat next to me.

•**Her** “So you’ve never had anyone touch your cock either then”

•*Me* “Nope, only myself.”

•**Her** “May I?”

•*Me* “Um… of course”

She smirked at me and grabbed my sweatpants, pulling them down my legs until they were fully off, leaving me in only my boxers. My dick was bulging through my underwear and you could see the outline of it through the fabric.

•**Her** “Damn, you’re hard as a rock arent you.”

She giggled and reached over my crotch. She ran a single fingertip softly along the length of my dick, back and forth multiple times. My dick twitched suddenly, getting harder and harder with each pass of her finger. Then she gripped my dick through my underwear still and stroked it a few times before stopping.

•**Her** “Hey! I have a fun idea!”

•*Me* “‘What’s that?”

•**Her** “I used to work at gentlemans club years and years ago. I haven’t given a lap dance in so long but I kind of want to give you one now. I always thought they were really fun. Do you want one?”

•*Me* “Yeah! That sounds awesome”

She was giddy and seemed really excited to give me a lap dance. She grabbed my hand and hopped up off of the bed, leading me back into the living room toward a big armchair. She ordered me to sit down and I obliged. She walked toward me and stood with her back toward me and bent over, placing her ass inches from my face and shaking it around. I reached up and grabbed her butt but she said:

•**Her** “Nope! No touching. Put your hands on the armrests and sit back.”

I did that and sat there with my hands grabbing the ends of the armrests. She bend down further and grinded her butt against my crotch, wriggling it back and forth. It felt like my cock was going to burst through my boxers I was so hard. My dick ended up placed perfectly between her cheeks as she slid back and forth. It was at this point that my pleasure started to build up exponentially. She kept doing this for minutes, sliding back and forth and side to side, her butt pressed up against my dick. I really started to feel the pleasure welling up to the point I felt like I might cum if this continues. I was breathing heavily and I couldn’t stop a few soft moans and shuddering breaths from escaping my lips. My thighs tensed up and I started to reach my breaking point where cjmming was inevitable…

But she suddenly stopped, stood up straight, and turned to look at me. I sat there, still taking deep shuddering breaths. That welling up sensation begin to subside but I could see a small wet spot on my grey boxers near the tip of my dick from leaking precum.

She slid off her pants as I watched her, leaving her completely nude except for a pair of lacy black panties. Then she climbed on the chair and over top of me with her knees on each side of my legs as she stared into my eyes, grabbed my shoulders, and began to grind her hips back and forth. I could again feel the warmth radiating from between her legs as she grinded back and forth, the only thing separating my dick from her pussy being two thin pieces of clothing.

I could feel the bulging outline of my cock between the lips of her pussy, spreading them apart as I slid between them each time she moved back and forth. I resisted the urge to grab her hips and just sat there, alternating between staring deep into her eyes, to looking at her breasts, to watching her hips moving on top of my crotch.

The pleasure began to build up once again, stronger than ever. She kept moving around like this for a few minutes, and each time she slid forward and my dick passed between her thighs I got closer and closer to the point of no return until I was seriously struggling to not cum. My breathing was labored and I was shaking, fighting with everything I had to not bust in my underwear yet. Eventually, It started to feel inevitable so I spoke up.

•*Me* “I think I’m about to cum.”

All she replied was “mmmmm” and continued grinding on me. At that point, I couldn’t hold it back any longer. I felt my orgasm begin and let out a long, loud moan as I let loose, my legs shaking beneath her. She kept moving, but leaned foward to kiss me. I could barely kiss her because of my heavy breathing. Her tongue met mine and out lips locked tightly together. I could feel my cock pumping cum spurt after spurt, emptying my load onto my pelvis and soaking my boxers. She kept kissing me until my orgasm subsided and my breathing slowed. Then she pulled away and got on her knees in front of me, pulling my underwear down my legs.

There was a pool of cum gathered on my pelvis and grabbed my cock in her hand, held it straight up, and leaned forward to lick the cum off of my body. She licked it all up and then swallowed it before standing back up.

•**Her** “‘Holy shit, I can’t believe you came just from a lap dance.”

•*Me* “Sorry, I tried to hold it back but -”

•**Her** “No, no it’s okay. That’s actually really fucking hot. I hope you aren’t finished though, I want to do more.”

•**Me** “No I definitely want to do keep going”

•**Her** “Good. Some guys are done once they cum. What should I do with your boxers? They’re covered in cum.”

•*Me* “Uh, I don’t know. Just put them somewhere so it doesn’t get all over your carpet or something.”

•**Her** “Okay, I have a few pairs of boxers if you want some to wear back home when you leave.”

•*Me* “That would be good, yeah, thanks.”

She picked up my cum covered underwear and took it to the bathroom. She put them in the sink and ran some water over then to rinse them out amd left them in the sink. Then she came back with paper towels, one wet and one dry. She wiped me off and dried me then threw them away. Then she motioned for me to stand up and follow her back into the bedroom. We both got back onto her bed and laid down together, cudding. She saw my cock had gone soft and reached down to rub her hand over it.

•**Her** “Lets give you a bit to recover before we move on.”

We laid there together, making out with our bodies intertwined and our tongues dancing together. Her hand was resting on my crotch but not moving or gripping my dick. About 10 minutes later I felt myself start to get hard again. Once I was fully erect again she kept kissing me but wrapped her hand around my shaft and began to stroke it slowly. Our kissing became more passionate as she continued to stroke me. This continued for a few minutes before she pulled her face away from mine and she sat up with her hand still gripped around my dick.

•**Her** “Hey is it possible you can stay all night?”

•*Me* “Yes, why?”

•**Her** “And do you think you can keep going if you cum again?”

•*Me* “Probably, why?”

•**Her** “We still have lots to do, but I don’t want to wear you out too fast.”

I laughed, telling her that I didn’t think that was going to be a problem. She smirked back at me.

•**Her** “Get up, take your shirt off, and stand against the wall”

I got up, removed my shirt, and stood against the wall. She got off of the bed and walked over to me. She pressed her hands against my chest and leaned in to kiss me. Then slowly moved down, kissing my neck, down my chest, and eventually to my cock. She took it into her mouth and began to give me the first blowjob I had ever had. The pleasure was instant and intense. I could not believe how incredible it felt.

I could feel her tongue wrapping around my shaft as she bobbed her head back forth, sometimes gagging whenever she went too deep. Whenever she gagged she would pull away and jerk me off for a moment as she caught her breath. At one point she told me to let her know when I was about to cum. It took around 15 minutes before it got to that point. I was nearly at the edge and told her I was close.

She stopped sucking me and pulled away, jerking me off over her face. A few seconds later I came, shooting a surprisingly large load onto her face. She cllsed her eyes and moved around her head around so it got all over her. It covered her nose mostly with some spots on her lips cheeks, and forehead. Some also got over her eyes and into the bangs of her hair.

Once I was finished cumming she opened her licker her lips but didn’t move, keeling her head tilted up so the cum didn’t run lff of her face.

•**Her** “can you get me some toilet paper from the bathroom.”

I went to the bathroom and got her the toilet paper which she used to wipe off her eyes. She didn’t wipe off the rest of the cum and kept her head tilted up. She opened her eyes and looked up at me

•**Her** “Can you grab my phone and take a picture of me? It’s on the dresser.”

I was surprised but said sure. I got her phone, she gave me the pin code, and I opened the camera and took a photo of her cum covered face. Then I turned the phone around so she could see the picture.

•**Her** “That’s so fucking hot. Thank you.”

She wiped her fingers across her face and collected some of the cum, sucking licking it off of them. Then she wiped her face with the toilet paper before standing up and going to the bathroom to wash up. I laid on her bed and waited for her to return. When she came back she laid down next to me and grabbed my hand, moving it down and underneath her panties then letting my hand go. She was soaking wet and I rubbed around for a minute, feeling her pussy. I could feel a small tuft of hair at the top.

•*Me* “So why did you want that picture anyway?”

•**Her** “Just to remember this by. Plus I love facials so I love seeing my face covered in cum.”

•*Me* “Send it to me when I leave”

•*Her* “I will. You should look at it when you jerk off and think of me.”

•*Me* “Oh, I’ll definitely be doing that.”

I slide two of my fingers inside of her pussy for the first time. She gasped. I slide my fingers in and out for a minute or so before she reached down and grabbed the back of my hand.

•**Her** “Do it like this… curl your fingers a little bit”

I bent my fingers inside of her a bit and she guided my hand, moving it in a motion that slid my fingers up and backward at the same time.

•**Her** “You don’t want to just move in and out, do a slow scratching motion with your fingers along the top. Okay? Now try it.”

She took her hand off of mine and I did as she said. She coached me a little bit more until I got it right.

•**Her** “‘Okay. Now sit up and move down toward my legs so you can get a better angle. Take my panties off and do that for a while. ”

I moved as she said and slid her panties off, seeing her pussy for the first time. She spread her legs and I slid my fingers inside of her again and did the motion that she taught me. She stsrted squirming around and moaning.

•**Her**”Yes, just like that. Fuckkk. Keep going.”

I kept fingering her, watching her grio the bedsheets and squirm around beneath me. She told me to speed up after a while and once I did her moans got louder. Sometime 5-10 minutes later she moaned:

•**Her** “Don’t change anything, just keep going like that. I’m getting close.”

Moments before she came she started breathlessly saying “fuck, fuck fuck, fuck” and then screamed when her orgasm began. I could feel her pussy tighten and convulse around my fingers. She gushed with wetness and my fingers made a rhythmic sloshing noise as they moved around inside of her. She grabbed a pillow next to her and hugging onto it tightly. Her whole bodh vibrated. Her scream turned into moans as her orgasm subsided and her body relaxed. She then spoke up, between labored breaths.

•**Her** “Now… I want you… To… Eat my pussy… Go ahead.”

I laid down on my stomach and kissed her inner thighs. I could smell her pussy and it was the most intoxicating smell I had ever experienced. I immediately loved it. Then I moved inward and licked her pussy. I loved how she tasted too, and it was at this moment that my love for eating pussy was established.

I buried my face between her thighs and ate her out for probably 15 minutes, with her coaching me where to lick and how to move my tongue around. I slid my tongue deep inside of her at points, but mostly focused on clit. About 15 minutes later she came again. I gripped her thighs tighter and kept eating her the whole time. She bucked her hips into my face over and over and eventually she relaxed. I kept licking her slowly for a few minutes until she told me to stop. I pulled away and sat up.

•*Me* “I fucking loved that. That was amazing.”

•**Her** “Me too. Now come here and kiss me.”

I kissed her for a few minutes until she pulled slightly away and whispered

•**Her** “Now lie down, lets fuck.”

I laid on my back and she mounted me, straddling my legs but not putting my cock inside of her yet.

•**Her** “You can cum inside of me if you want. I’ve had my tubes tied so I can’t get pregnant.”

She then reached down and grabbed my cock and slid it inside of her, and in that moment I was no longer a virgin. She sat straight up with her hands st her sides, bouncing on my cock. Eventually she pressed her hands onto my chest to support herself and moved quicker. I reached up and grabbed her tits for a minute before moving down and holding onto her hips.

She kept fucking me for 10 minutes until I came inside of her. My orgasms were super intense at this point as it was my third one in roughly 2 hours. My body was absolutely rocked with pleasure. I could feel my dick throbbing and pumping inside of her, all of my muscles tensed up, and I let out a deep growling sound.

She never stopped fucking me even after I came. I was so sensitive that each bounce made me gasp. It started to get too intense but she seemed to habe no intention of stopping, and I said nothing. I didn’t get soft either. A minute or so later she came again too and collapsed over my body with her head buried in my neck and my cock still inside of her. I could feel her heavy, hot breaths on my neck and my cock twitching inside of her. She wasn’t moving but the warmth, wetness, and tight squeezing around my shaft threatened to push my still sensitive cock over the edge again.

She sat like this for a few minutes, totally worn out, still breathing on my neck and kissing it. Each slight movement of her hips pushed me close and closer to cumming again and eventually I couldn’t stop it again. Once there was no stopping it I grabbed her by the chin and lifted her head up until her face was right in front of mine.

I stared into her eyes and let out another, long, deep growl as I hit my tipping point, cumming once again. We just stared at each other while I held her chin. Her mouth was agape and she gasped and got wide eyed. This orgasm lasted so long. It was 10 seconds later at least before it finally stopped. Once it was over she whispered

•**Her** “Holy fuck, did you just cum again?”

•*Me* “‘I did.”

She leaned forward and kissed me for a few seconds, then climbed off of me.

•**Her** “I’m worn out, fuck. Let’s relax for a bit.”

She went to the bathroom while I laid down. There was a mixture of my cum and her wetness covering my cock. Once she came back she saw this.

•**Her** “‘Oh, let me get something to wipe you off with — actually…”

She cut off mid sentence and climbed onto the bed, getting down onto all fours between my legs. She licked from my balls up my shaft and thrn grabbed my dick and licked the other side. She swallowed it and then went and got me a towel to clean the rest off.

After this she put on a movie and we laid on the bed and cuddled while we watched it. We would make out occasionally and I would play with her breasts or grab her ass and pull her closer. Once the movie was over I ate her pussy for a while longer and then fucked her in missionary, until she eventuslly flipped over and got on all fours, raising her ass up. I grabbed her hips and slid inside of her, fucking her from behind until I came again.

After that she laid back down and I fingered her and ate her pussy until she came one last time. By this time it was very late, so we turned off all of the lights, got in bed under the covers and went to sleep together spooning naked.

She woke me up around 9am saying she had to go pick up her daughter at 12. We fucked one last time and then she got me a pair of fresh boxers from her dresser and I got dressed. I took my original pair from the bathroom and left.

We met up about 4 more times afterward and it was always an incredible experience. Thanks for reading if you made it this far. I have a few more interesting stories I will post at some point, but these take hours to write out so it might be a week or two.

Source: reddit.com/r/gonewildstories/comments/twe37n/the_story_of_my_m_first_real_sexual_experience_of