TL;DR: I was 21 and fucked an older woman (46) from a dating app at a hotel.
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Hey there. This is my first time posting so hopefully I don’t break any rules or anything. I’ve been reading some of the stories that last couple days and one story in particular made me want to write about my first time with an older woman hoping that someone would like it and I get to relive it a little.
So it all started on an app called whisper. Whisper is an app where you can make anonymous posts about just about anything, but the posts can be responded to with direct messages and eventually photos, sort of like it is here. So this 46 year old woman posted on her whisper, “I miss being young, enjoy your younger years”. I was just a horny little 21 year old searching whisper, looking to make a connection that lead to something more than just a connection. And in the back of my mind I had hoped that it was an older woman because I had never been with an older woman. I saw her post and replied, “I can help you feel young again ;)” super cheesy, I know, but at the time I thought it was a good one lol. I know she thought it was a cheesy line but something made her reply, maybe it was her seeing my age range, I don’t know.
So we ended up starting with the standard introduction of how old we were, what our names were, where we were from, and shared pictures. I’m no Prince Charming, more of a shrek lol, but I caught her attention and boy did she catch mine. The first pic she sent was of her cleavage showing, on up to her face. But she had her index finger kind of in the corner of her mouth. She had her down to her shoulders, blonde, beautiful face, and her boobs were a great size.
Next thing you know we exchanged kik accounts, that was big at the time lol, and we just started to get to know each other better, but not too well. We of course started talking about our favorite sex positions which would always turn me on. Nothing turns me on more than a woman talking dirty to me, especially an older woman. I was rock hard during these chats. She told me she loved anal, loved to ride cock all night, and loved to be loud. Even through all this talk though, she never would send me a nude even when she’d ask for a picture of my dick she would not send one back.
At this point, I figured it was time to meet in person and have some fun. We agreed to meet in a city that was the midpoint of our two cities for drinks and to get a hotel after. I didn’t want to book the hotel beforehand because I was still unsure if this was a too good to be true situation. As we were planning she was telling me how she wanted to get on her knees and suck my cock so good until it’s nice and hard so she can hop on it. I would tell her that I want to bed her over and fuck her doggystyle, then put it in her ass. The usual dirty talk.
So the day has come to meet. I admit, I’m a bundle of nerves probably the whole day for multiple reasons. 1) I’ve never been with a woman her age 2) I didn’t wanna fuck it up 3) I got to be on my A game, I can’t let her let me cum too fast lol 4) and most importantly I’m not even 100 percent sure this woman is real. I don’t trust the interest so I wasn’t sure. So on the day of meeting, I asked her to send a selfie of her in a specific pose. She thought it was silly but understood and did it for me. I’ll have to admit I was instantly relieved but still a bit nervous.
We make it to the bar. We meet in the parking lot, I see her and she just looks amazing. Blonde should length hair, her make up looked amazing (even though I like all natural), and she had on a mid-length tight black dress. Her boobs were pushed up nice, and I couldn’t keep my eyes off of her hips and thighs. She also had on some heels that looked amazing on her. In my head I kept thinking, there’s no way she’s going back to the hotel with me lol. We give each other a friendly hug hello, and she plants a little kiss on my cheek, instant smile for me.
We make our way in, I order myself a jack and coke with a double shot and a large Kona big wave and ordered her a mint mojito that she asked for. So there we sat talking just about shit like music and tv shows. Then we made our way to the pool tables and started a game. The way she was bending over the table in that dress just started getting the juices flowing for me. It wasn’t like in the movies or the pornos where the girl exaggerates bending over but it was a beautiful woman with a full ass bending over in a tight dress none the less. I was giving her compliments and she was smiling, turning a little red, maybe from my compliments, maybe from the alcohol, or maybe both. We keep playing and drinking, she’s starting to warm up to me and starts grinding on me to the music and just kind of backing up into me. I took that as a signal and turned her head towards mine, and started making out with her. Right next to the pool table. I asked her if she wanted to take a shot and she said in my ear, “that’s fine, but only one round. I don’t want you getting whiskey dick later” and licked my ear. I had to try and regain myself because I was getting turned on right in the middle of the bar.
Our shots show up, we cheers and shoot them down. It’s pretty close to midnight at this time and she tells me, “I think we should do something else right now” and gave me a little wink. So I paid the bill and we walked to our cars. I gave her the address to the hotel that was down the street and told her to meet me there. It was a nice hotel too because I felt like I had to do it right, this was a momentous point in my life history lol.
So we meet in the parking lot, and I told her I’ll go check in. Me being young and never needing to get a hotel room, never knew that it was practically impossible to get a room without booking it ahead of time. So I thought I had fucked myself out of this very fun time, I was so pissed at myself and I was not about to fuck an older woman in the back of a car. So after I dealt with the receptionist, I quickly looked up hotels close by. Found one less than a mile away, not as nice but it was nicer than a motel and definitely better than the back of a car lol. I called them and asked if they had rooms available and luckily for me, they said they did but only a 2 bed available. I said that’s perfect I’ll be there in a few. I made my way out to the parking lot, honestly a little nervous on how my date would take the news, but she thought it was hilarious and gave me she about it lol. So finally after she was done making fun of me for my fuck up, we made our way to the other hotel. I get inside, pay for the room, get my room key, WiFi password, and number and I’m set.
I tell my date we’re good to go and she comes walking in and goes right to me. I think we got some judging eyes from the receptionist but who cares lol. We make it in the elevator and she’s literally right up on me, I’m feeling her through her dress, we’re ready to go.
We make it to the room, I’m shaky as fuck putting in that card key lol. Like so shaky lol. We walk in, put our stuff down, and she comes right up to me making out with me whilst reaching for my cock over my pants. She does the little lip bite, which I love, and starts kissing my neck and chest. At this point, I’m all the way turned on, and start unzipping my pants. Pull my cock out and immediately as it flings out of my pants she starts stroking it. I’m no monster, I’m like 6 inches hard, half an inch soft lol. I whisper in her ear, “id love for you to suck my cock so good like you said you would” she kicks her heels off while saying “gladly” I grab a pillow for her knees and she gets down and slowly just starts licking the side of my shaft up to the tip. Then doing the same on the other side. Then she started teasing by only putting the head in, fuck that was messing with me so bad. Finally, she put the whole thing in her mouth and started sucking away. Still to this day, some of the best head I’ve ever gotten. Perfectly wet and stroked my cock perfect.
After minutes of my cock being sucked, she said “I want you to eat my pussy” how could I refuse? Instead of taking her dress off, she had her tits out and panties off. I thought that was so fucking hot. I laid her on her back and started licking her pussy like a thirsty dog. I wasn’t the best pussy eater at the time but I at least knew to stimulate the clit so I wasn’t worthless lol. She was loving it, would shove my face deeper into her, until I’d have sort of a drowning sensation and when I’d come up for air my face and beard was covered in her pussy juice and my saliva. We were so turned on for each other.
Then she yelled to me, “I want to ride that fat cock baby, I need it!” I don’t know how I lasted with this woman, she was amazing lol. She got on top and had so much energy. Way better at riding cock than any girl my age. Most of the girls my age were so lazy at riding cock or just not experienced. But as I she was tiring, I started pumping her from the bottom. Her moans starting turning into kind of a low growling sound, it was so hot. I wanted to fuck her so bad that I told her to take her dress off and get on all 4s on the bed. She listed so quick which was so hot. And I just slid my hard wet dick in there and started pumping. Hearing the sound of her wet pussy, my balls smacking her pussy, and her moans/growls. Also me being an ass guy I got to play with her asshole. Sticking my thumb in there and spanking it. It was a perfectly clean hole.
She told me she wanted me to cum, and stupid young me that doesn’t know any better at the time asks, “well, have you? I don’t want to stop until you cum too” and she said “yes I have” and chuckles a little. So while I’m pumping her pussy from behind, I start getting more intense. And I start pumping faster. I tell her I’m getting close. She’s saying “fuck yes, cum for me” and I ask her where she wants it. She says “all over my face” fuck that turned me on even more. I get right to that point before orgasm, and I pull out quick and say turn around. Got right over her face and stroked my cock until it came out all over her face. I don’t think I shot out that much cum until that point before. She licked whatever cum she could on her face and cleaned off my dick with her mouth and said that was fun. I got her a towel to wipe up and I cleaned up after her.
We just laid there for a little after and turned the tv on. Laying there with each other naked. It’s about 2:30am at this point. I’m flipping channels and she’s laying there talking, still playing with my cock. Then the weirdest thing happens that she says. I flip passed a show and she says “oh my husband loves that show” and in my head I’m like “what the fuck” lol I was like, “oh shit you’re married?” And she’s like, “yeah, I thought I told you?” And I was like “no” lol. I was at a loss for words and felt like such a scumbag lol. She said, “I hope you don’t mind, while stroking my cock and looking at me seductively” and in my head I’m like I know this is so wrong but fuck it lol and I said “no, it’s fine. I think it’s fucking hot” and we started making out…
Well I’m gonna end it here. Hopefully you guys liked my experience. It was fun to revisit it in my brain and write it down lol. If you have any questions about the story I’ll answer. I do not talk to her anymore. I did not contact her after that because I wasn’t trying to deal with a jealous husband. And we fucked until like 5:30am and she was gone right after she showered. It was amazing. Thank you guys for all your great stories too!