Hey! This is my first ever ISS story and it’s about from a dating app. I am a 19 year 5ft 7 inches guy with a sculpted build based in Delhi. I am going to talk about my recent experience with you all.
I downloaded Bumble (a dating app) to see what’s it about. I was bored by the cringe or uninteresting Bios of 18-19-year-old girls. So I switched to 40+ yr old. To my surprise, there were 10-15 women, and 8-9 were pretty cute. I swiped right on them as they were ‘verified.’
I had stopped opening the app as soon I got bored with it. But then, almost two weeks later, I got a match with a 44-year old surgeon woman. I would not say she was well-maintained. But she had perky (a pushup bra, I later found out) tits and did not have that much of a belly.
According to the rules on Bumble, it’s the woman who has to start the conversation. So she sent a simple ‘Hey’ to which I reverted. After some basic info, she asked me, “Why did I swipe right on me?” I replied, “You seemed very attractive.” We continued flirting.
I came to know the following details. She was divorced. She had a son of 24 years of age who encouraged her to create a profile a year ago. She has had her adventures over this year (pre-COV-ID) with young guys.
I told her all my troubles too about how I broke up. She just laughed and said that it reminds her of her old days and dated her boyfriend (now ex-husband).
I still had to make sure if it was really her. So I asked her out, and she asked me to pick her up from her house. I declined as I thought this could be a trap. So, I picked her up from the ‘Chanakya Mall.’
I did confirm from a distance if it was her. Boy, oh boy, was she beautiful! She didn’t have a fine figure but sure looked like a MILF! I guess being a doctor, she took good care of herself as she had amazing skin.
She had worn normal jeans and a bit of low-cut top in a cheetah/leopard print. She was well endowed and was up to my height. I then met her and talked for 2 minutes and decided to go out in the car with her. Now, we had no plans as to where to go. So I just drove while talking:
Me: So, what do you expect from me?
She: Honestly, I just wanted to have sex. But I feel like going out with you to a movie.
We went to the nearest Theatre and got a couple of tickets for the next show. She felt a bit cold in the hall, so I gave her my jacket. I did initiate holding hands. We ended up talking mid-way and were talking about the best experiences of our sex life.
She said she wasn’t that much of a kinky person. But she had tried dirty talk and getting her ass eaten by her past hookups. She told me she got into younger guys cause even guys 10 years younger than her were just not that attractive. The one that made it to the bed was just not good and was not clean.
I saw her getting a call from her son, to which she said, “Okay, you go ahead, see you tomorrow.” I asked her about it. She said that her son would stay at his colleague’s house as he anticipated us having sex (as it happened in the past).
I got more and more attracted to her as we spoke. I got the courage to keep my hand on her thigh. She moved a bit but liked it. I believe as she kept her hand over mine. I gently rubbed my fingers on her inner thighs. She liked it as she opened up her legs a bit.
I wanted to tease her and asked her to go into the washroom to make out as there was a crowd in the hall. We went into the women’s washroom and entered a cubicle. It was not ‘hands all over each other.’ But I gently held her waist, pulled her close, looked in her eyes, and moved in to kiss.
It was a great 10-second kiss before I felt her hands trying to reach my crotch. I stopped and broke the kiss. I said to her, “I’m not going to be your one-night stand. I’ll make you fall for me.”
I know it looks impossible to miss such an opportunity to get a blowjob, but I was attracted to her. I left the washroom and waited for her outside. She came looking all confused, and I said, “Just come with me.” I took her to a restaurant. We had a nice dinner with a good conversation
She: Why did you stop and not continue?
Me: I did that cause I want to do you properly. Yeah, quickies in public places give an adrenaline rush. But since it would be our first time, I want to do you on a bed with a good time on our hands.
She: That’s quite a plan. You gave it a lot of thought. I guess you like me.
Me: I do. I genuinely like you and can’t wait to ravish your body.
We split the bill as she insisted, and then we went to her home. As soon as we entered, now was the ‘hands all over each other’ moment. She threw her purse and got rid of her heels. I took away my belt as she kissed my neck while unbuttoning me.
I then pushed her on the sofa and there, was the fire in her eyes. Now it felt like she had wanted me, not just wanting to do it. I grabbed her neck and brought her face to my lips as we made out. Her hands were rubbing all over my back. I picked her legs up and put them on my shoulder to dry hump.
I give her a feel as to what would happen. I took her jeans off and, still dry humped. Now I wanted to see her tits, and I did just that. I threw her top and bra one by one behind the sofa. Don’t we guys love the feel of boobs? They might be saggy, but they were soft and just so good to suck on too!
I did get an “Aahhh. You’re sucking them spot on!” I then again dry humped her as I started chewing on her lips.
She: This is just like the first time I ever had! Even my hookups were not this hot! Go down on me! (she was gasping for air)
I then kissed from her neck to the navel and then removed her panty. It was wet due to all the humping. She moaned as if she felt her pussy being let free, and she spread her legs. I saw her pussy lips a bit parted. There was no hair down there. Although the skin was dark, her pussy smell was musky and erotic.
I kissed her thigh and licked the area around her pussy. Her legs were moving around, and she put one of her hands over my head. She moaned uncontrollably this time as it was turning her on. After doing the same for a minute, the musky smell of her pussy was calling me.
I reached the bottom of her pussy and started licking all the way very slowly up till I reached the little clitoris. She let out a big moan while I did this as being slow adds to the pleasure.
She: Where did you learn all this?
Me: I learned it from my ex’s preference.
I gave her a lick again.
She: Oh my god! Do that again! She must have made you a god in bed!
Me: Not god, but I would get her off!
I was again licking up to her clitoris.
She: Oh! That’s the best way anyone has ever eaten my pussy! Suck on my clit too!
Me: Anything to get you off!
I did just that! And her legs wrapped around my head, not letting me move. I could feel her thick thighs around my neck. It felt so hot. I continued sucking on her clit and giving it a press by my tongue.
She: Ahhhh! You’re the best! Ah, do that, yes, right there!
I pushed her legs open and stretched them as much as I could. I then licked very fast, just on her clit, and I spread those legs as wide as possible. I continued with the same rhythm, and soon her legs started shaking
She: Ahhh, I’m coming, right there, don’t stop, oh yes, yes, yes, yes.
I did not let her take control of her legs and held them in the same position while licking. Her body got desperate to move them around. She came hard. There were no juices all over me. There was a liquid flowing out of her pussy as her legs came to a rest, and she was catching her breath.
I could see her pussy lips pulsating from the orgasm. She took a minute to come back to her senses as I watched her open her eyes to see me sitting and looking at her.
She: Ah, that was just something else altogether. I guess it’s time for your turn now.
She got up and gently came and sat on my lap. We kissed in that position as she dry-humped me this time over my boxers. It was very hot, and I laid my neck back as she kissed me on my neck while humping.
She: Tell me how you want it. I want to return the favor in the best possible way.
Me: Well, I like to take control.
She: Oh, so what do I have to do (kisses me)
Me: Just follow whatever I say, even dirty.
She: Okay, let’s try that.
Me: Get on your knees in front of my dick.
She got down on the floor between my legs and tried to take my boxers down. I slapped her hands away.
Me: You slut, you do as daddy asks!
She: Oh, daddy, I like that.
Me: You deserve a spanking,
I pick her up and take her to the bedroom. I threw her on the bed and asked her to get on her fours
Me: This is what you don’t get for obeying daddy!
I spanked her very hard.
She: Oh, that hurts.
I continue spanking. I then turn her around. I put my dick in front of her face and grabbed her hair bun and the neck with the other hand. I put my 6-inch dick in her mouth. It was hitting her throat, and I pushed it in and held it for 5 seconds. I took it out, and it was full of her saliva.
Me: Now suck daddy’s dick like a good bitch.
She: (speaking while my dick is in her mouth) Yes!
We did that for 5 minutes, and then I pulled it out of her mouth. I turned her body around.
Me: You ready to be fucked by daddy?
We were now in a missionary pose.
She: This pussy is burning for that dick.
She was rubbing it as she spoke. I pushed it in without wearing a condom. The feeling of doing it raw is amazing. Her pussy walls were very hot from all the humping. I could feel the wetness of her pussy till the inside all around my dick.
She: This is so good!
I started very slowly and even held for 5 seconds between strokes. I played with her boobs while she moaned with her eyes rolled up.
“Ahhh, just like that! Oh yes! Fuck me, daddy!”
I increased my pace a little bit. She loved that as she had totally submitted to me and was now under my control. I then stopped and picked her up, took her in front of the mirror. I made her put her hands on the dressing table and bend into the doggy style.
I spread her ass apart and put my dick in her pussy. We made eye contact looking into the mirror as we fucked.
Me: You like that, you filthy slut!
She: This…is…the..best…I…have…ever..had. You are doing me so well.
This made me hot. I pushed my dick all in and held and pushed her whole body towards the mirror. Now her whole body was next to the mirror, and I fucked her in the standing up position. She was moaning. I got so hot from this, and I pulled out.
“Get on your knees. I am about to cum.”
“Cum on my face.”
I came on her face. I asked her if I can take a picture as a memory of this day.She agreed. (I still have it ) It was so hot. I then pulled her up, and both of us lay on the bed.
She: This was the best experience of my life. I had never thought sex could be so good.
Me: Was? We are not done yet.
She: Oh, I like the stamina. You meant it when you said you would ravish my body.
“Get on all your fours. The punishment is not done yet.”
She got on her fours in excitement. I brought my belt from the sofa outside and got back in. I take her hands behind her. She falls on the bed with her ass high. I tie her hands with the belt and then go in front of her. I pick her face up as I lay down and placed my dick under her face.
I asked her to lick it. She did that for 2 minutes to my limp dick and brought it back up. She licked it well. I then held her neck and forced my dick deeper. She was making gagging noises. I kept it there until she started resisting. She looked up to me, red eyes, horniness still there in them, and gasping for air.
I then turned her around into the doggy style. I put my dick in and fucked her for 15 minutes this time. I had learned a lot about how to last long from blogs, and they came into use. I then made her ride me, she was tired as fuck from all the action, but I pushed her to do it.
It got so hot as she moved her butt around my dick so good that I came again. I realized she had only come once all this while. I pushed her on the bed, and I switched to using my fingers this time and did it pretty roughly. It was hurting her, but the pussy juice would lubricate it.
I would lick in between as a cherry on top and suck hard on her clitoris while fingering. She came too, this time. We were tired as hell, and she then turned and lay on my chest. She breathed on my neck as I caressed her butt.
Me: I told you you would fall for me.
She: I guess I did.
We then slept. I went home the next morning after a morning make-out and blowjob from her. It was an amazing experience. The lockdown was imposed, and we sexted. But it lost its charm, so we got disconnected.
I named myself Anonymous Gigolo as a Gigolo gives a woman a good time. They don’t need to make money. I would love to talk with a reader of my story. Ping me on .
Thanks for reading the story of how , everyone! I hope you have a good time.