[MF] She wanted to lose her virginity to an experienced, older man.

I love using dating apps to meet new people that I wouldn’t otherwise and such was the case with Kat. One evening, I decided to increase the acceptable age ranges on all of my dating apps, curious if anything new would come of it. Now that I’m nearing 40, the prospect of being with someone in their 50’s or 60’s sounded attractive but so did being with a younger woman in her 20’s. After all, younger women are supposedly attracted to older men, right? Such was the case with Kat.

I woke up the next day to find a bevy of new prospects in my inbox. Kat was a college student living on campus and, at first, I thought she had to have made a mistake. Her profile said she was 21 and just turned 21! I would have sooner matched with her mom, who I probably have more in common with than her but damn she was cute. She had somewhat curly brown hair, glasses, blue eyes and an incredible smile that shown through in all of her pictures. I sent her my standard opening message and she responded a few hours later. I’ll spare you the details but I like to meet in person rather than text forever so I asked if it would be okay if met for dinner and she agreed. The date was set for the next day.

At 6pm, I arrived at my usual first date restaurant. It’s a higher end bar and restaurant near my office where the music and noise isn’t so loud that I would struggle to hear the conversation. As I exit my BMW, I see someone sitting at the door and my heart flutters a little. Is this really happening? I walk to the entrance of the restaurant and I just can’t stop from smiling and my hazel eyes light up as I get a closer look at Kat. She’s even more cute in person than in the photos, wearing green cozy sweater and jeans. She greets me with a hug, which was unexpected but very nice. Our size difference is noticeable. I’m 6 foot tall, a former college athlete, and what I would describe as an in-shape dad bod.

Normally, I ask my date what her favorite bottle or type of wine is and order that for us to share but she wouldn’t know wine yet so I ordered a nice bottle of Pinot Grigio. I’m also not new at dating however she totally disarmed me with her smile. We spend the 45 minutes just getting to know each other as I needed to put aside the notion that she may be here just for a free meal. At some point, I decide to broach the elephant in the room.

“I hope this doesn’t come across wrong but why did you select me?” Normally, a question like that would be the death knell to any notion that I had a shred of confidence in myself but I was curious to know where this was going. Besides being attractive, we had very little in common.

“Well…” she said, mustering up the courage to continue, “I have been dating guys my age for awhile and I’m looking for a new experience.”

“Experience?” I asked.

“I’m 21 now and I’m ready to have sex but I don’t want to have sex with anyone. I had a fantasy of how I would like my first time to be yet, when my friends talk about the sex they’re having, it’s always negative. My friend’s boyfriend always wants her to go down on him but he hasn’t once done the same to her, saying it was gross. Another met a guy who was really great and nice but, when the time came, he just couldn’t get hard. I don’t want that for me. I want someone who knows what they’re doing at least. Plus, I really liked your photos.” I had a photo with me and my dog

“I don’t know what to say but I would love to give you the experience that you’re looking for. My first time was incredible and I wish everyone could say the same”. Then I added “however, sex between partners only gets better with time” hopefully setting up for a future rendezvous.

My mind when into overdrive. How do I give this girl the best first sexual experience that she could hope for. So I ask “tell me about your fantasy”?

“He knows my body better than I know my body. He takes control and uses me for his pleasure. Whatever he wants, I’m helpless but safe in his hands”. I now had my work cut out for me. I offer to drive her back to campus and we make an arrangement to get together the next evening. In the car, she holds my hand and leans her head on my shoulder. Every so often, I would catch her glancing up at me and every time I did, my heart would flutter. At one stoplight, I turned to kiss her on the lips. At the next, she returned the kiss. At the next, the kisses became more intense until we were back in front of dorm.

The next day, I set my plan to motion. I booked a room at the Ritz Carlton with a large single bed, a bath tub and large two person shower. I stocked the room with water, a couple bottles of wine, 4 dozen red roses, condoms and lube. Soft music was playing on the speaker to drown out the noise from the city below. I went for a manicure earlier so my nails were short and I was wearing the same cologne that I did the say before. I was anxious and gitty at the same time. Would she even come? Then a knock at the door…

It was Kat, carrying a small bag of clothes and things in case she wanted to spend the night. We kissed immediately upon her entering and then I stepped back and let her take it all in. She was impressed. “You did this for me”?

“Yeah! It’s your first time and tonight, I want to fulfill your fantasy”. We then kissed, even more passionately and I could feel her heart beating through her chest. I was dressed a tailored blue suit, with a white shirt with cufflinks and a silver tie. Kat was wearing a coat over a sweater with tartan skirt and chunky heels.

I started kissing on her neck and nibbling on her ear. She giggled and moaned at the change in sensations. I took her hand and led her near the bed to continue kissing her. I whispered some instructions softly in her ear “Tonight is all about you. When I do something that you like, tell me right there or there if you you’re two breathless. If you say don’t stop, I won’t until I feel you cum, which you will a few times”. I took my jacket off and then cupped her face in my hands for another kiss.

I ran my hand under her sweater and we continued to kiss. She as trembling in anticipation of what was to come. “You’re in my hands now. Just relax” which caused her to melt like butter. I unzipped her skirt, causing it to fall to the ground and lifted up her sweater to reveal her matching black bra and panties. Being so small made her size B breasts look big and the skirt had been hiding a nice round ass and thick thighs. She rubbed against my pants and felt my hard cock pulsing. She went to reach for my belt but I backed her onto the bed to lay her down. “Tonight is about you” was the last thing I said to her as I kissed her neck and then made my way to her breasts. I gently ran my tongue under her breast, around her large areolas, eventually teasing her until I was sucking on her nipples. “That feels so good” she with a half moan tone to her voice. I kept moving my way down her body, leaving kisses along the way like I was a traveler leaving breadcrumbs unti I was knelt on the floor, between her legs. They were trembling in anticipation of what was to occur, further evidenced when I rested the palm of my hand over panties, which were soaking wet. I removed her panties to reveal her perfect, full lips, and a small bush around her vulva. “Should I have waxed? I’m so sorry…” she uttered. “Your pussy is absolutely perfect, I promise.”

I slid my hands under her ass and held her in place while I enjoyed her pussy. She was so wet from anticipation and continuing to be with every lick around her vulva. Then I began flicking my tongue over her clit to tease her a bit more, each time I did, she would smile and moan. She was so distracted by tongue that she didn’t even realize that I had slipped my index finger in her pussy until I made the “come here” motion. She jumped! “What did you do?” I replied “that is your-spot and when I make this motion, it sends shivers u your spine.” She wanted more so I continued while flicking her clit with my tongue. I said to her “if you think that was good…” gathered her clit in my mouth and began to suck on it like I was eating a ripe peach. “KEEP GOING! DON’T STOP” so I continued until her orgasm. Her body shook and trembled, her ass still in my hands. I set her down on the bed and kissed her lips. She was still catching her breath from cumming so hard. “Good girl. There’s more of those to come” and then I returned to between her thighs. Once she was able to regain feeling in her legs, she loosely wrapped around me while I resumed softly lick her very sensitive vulva. I repeated by steps prior and added a long “hmmmmm” when her clitoris was in my mouth. Orgasm 2 came quickly after that.

I stood up and began to undress, causing her to sit up. First , my shirt and then my pants were laid on the side chair. My black boxer briefs were keeping a secret from her no more. As she removed them, my cock sprang forth and hit her head. My cock, while big, is girthy. I have the unique anatomy that my cock is long as its circumference.

“How is that going to fit and not hurt”, she asked. “Don’t worry, it will just fine” as I moved her onto the bed. Then, I mounted myself over her and inserted me into her pussy. It was so wet and tight. “Go Slow!”she added as I was careful not to hurt her virgin pussy. With every stroke, she began to open up further to accommodate my cock. I felt myself starting to cum from how tight her pussy was so I pulled out and went down on her again.

She asked if she could ride my cock so I laid on the bed and helped her get in position. She felt the large head of my cock against her asshole before sliding it back in to her pussy. Her eyes rolled back as she began to grind on me. “Your cock feels so fucking good inside me!” My hands were back around her ass again and I left one finger on her anus. “Don’t worry. I’ll help you take my cock in your ass too when you’re ready.” She came again and then leaned over to kiss me.

“Where do you want me to cum, baby” I asked. “I want your cum inside me. Will you cum inside me? Come inside me!” She became ever more desperate “I need your cum inside me! Give it to me.” This is the moment where I fully appreciated having had a vasectomy. She then proceeded to get in all fours with her ass in the air, her bruised pussy staring back at me like it just lost a fight. I inserted my cock, grabbed her hips and then proceeded to use her small body to jerk off. Eventually, my hard work paid off and I gave her a filling creampie in her pussy. I pulled out and collapsed on the bed. She went to grab her phone and also laid on the bed. When I looked up, her legs were spread in the air, and she was using the selfie feature of her camera to see how full of cum she was. I ran my finger along her vagina and bought it up to her mouth. “Do you want a taste?” I liked my finger and then stuck it back in her pussy to allow her to see it up close.

She ran off to the bathroom and I laid in the bed relaxing and recovering. Eventually, she came back in and asked if I would join her for a shower, which I did, resulting in us having sex again that evening.

At some point, we both fell asleep, her on my chest and my arm around her. In the morning, we awoke in much the same position and then turned to cuddle in spoon.

Source: reddit.com/r/gonewildstories/comments/p8u0kw/mf_she_wanted_to_lose_her_virginity_to_an