Well, since this is my first story, there's nothing better than starting at the beginning haha.
Before I start telling you about my experience of losing my virginity to an older woman, I want you to vote, so I know that you liked my experience and that I feel confident to continue with the stories. That said, let's get to the point: the story!
If you read my bio, you know that I'm slightly attracted to women older than me, and my first time was with an older woman. Did that influence my taste? That's a good question, LOL. I had my first sex when I was close to turning 16, and that sex opened doors for me and changed my life.
Her name is Ana (fictitious name), she is short, 39 years old, blonde, has a spectacular ass and a beautiful pair of thighs. She has two children and maintains a constant routine of walking to stay in shape. Ana is part of my mother and grandmother's circle of friends, so when she wasn't here at home or at my grandmother's house, it was the other way around, my family was at her house. She always looked at me and smiled at me, but I never interpreted it as anything more than a simple kind look accompanied by a beautiful smile. She has a very lively way of being, she is always happy and I always saw her as a great friend, and what a friend I had, haha. Everything started to change the day my mother was at Ana's house and needed to talk to me. Since my mother always leaves without her cell phone, Ana gave me hers so my mother could call me. However, the attempt was unsuccessful because my house is in a place where there is not much signal. So I received two audio messages on WhatsApp from an unknown number, it was Ana's number. It was nothing very important, just to take some forms to Ana's house.
A few days later, after saving Ana's number, she posted a photo on her status where she was wearing a red robe, lying down and apparently watching a movie. When I saw it, I casually commented: "Nice robe, huh, lol, I wish I was in that good life there." She immediately saw my message and made a move, inviting me to watch the movie with her, of course, if my girlfriend would let me. By the way, I didn't have a girlfriend, haha. When I said I didn't have a boyfriend, she kept asking how a young dark-skinned guy like me didn't have a girlfriend, and that if she were in my place she would generally flirt with everyone. Continuing the conversation, I told her that I'm not the kind of guy who flirts with everyone and even joked that I like women older than me, so she sent me an emoji with a naughty face, haha. I confess that up until then it was just a joke between friends, at least that's what I thought, until everything changed.
After a couple of days of talking very little, she asked me about what I had said a few days before. I was curious to know what it was, and then she asked me the following question: "Why would you want older women if there are so many hot young girls who are dying to give it up and lose their virginity?" I started by explaining that it was because I was attracted to older women, and at the time I didn't know what came over me and I said: "Just like you LOL". To my surprise, she also said that she was attracted to me and wanted to have a chance with me. I didn't reveal that it was a joke, but I asked the same question she had asked me before: "Why would you want something with me if there are other guys who are more mature than me?" She responded by saying that she liked my personality, said that I was a handsome, funny guy and that I showed a certain maturity compared to guys my age and even older men. That night, I decided that I wanted to have sex with her and told her that I would give us a chance.
I briefly remember her saying that she would love to kiss me and that she finds the little mole I have near my mouth sexy. I immediately asked her if she would only love to kiss me and she replied saying that she would love to do other things much more. I couldn't contain myself and told her that I was a virgin, which surprised her. I said that I really wanted to go with her for the experience. She agreed right away and started sending me lots of nudes and videos of her taking a shower, until we set a date for me to go to her house.
The day came and it coincided with the day I was going to a friend's party, it was her 17th birthday and I told my mother that I would only be back at dawn the next day, she was a little reluctant, but we talked until she let me. I told Ana that it was a deal.
The day began to set on that cold Saturday, the time was approaching when I would have sex for the first time, I got out of the shower and got ready, my waxing was perfect, my skin was as smooth as a baby's. Finally, I was ready, I kissed my mother, said goodbye and walked down the street, I walked to Ana's house, we live on the same street and it was completely empty, no one would see me entering her house.
When I arrived, I called her at the gate, she opened it and I went in. I waited for her to close the gate while I looked her up and down. My friends, what a work of art! She was wearing the same robe, black lace panties and no bra. Nervous at that moment, I tried to distract her and asked if she wasn't cold LOL, she laughed and kissed me.
We started kissing slowly. I started pressing her body against mine, grabbing her ass really hard. At that moment, my cock was really hard from all the excitement. She grabbed my cock and took me inside her house. Once inside her house, I started taking off my clothes like crazy. I barely took off my underwear and she was already on her knees jerking me off.
I was crazy horny and she knew it very well, so she grabbed the head of my cock and started to run her tongue around it, at that moment my legs trembled and she made me moan a lot. At that moment I was still standing, so she stopped sucking me, got up and took off my shirt, then she started to jerk me off and very quietly in my ear she started to say:
- "I know you're dying to fuck me, right?"
I was almost cumming, it seemed like she had cast a spell on me, I was completely held hostage by that woman. Then, with my eyes closed and her talking dirty in my ear while I jerked off, I replied that I really wanted to fuck her. She then pushed me onto the couch and got back on her knees.
- "Do you want to fuck me, do you? Do you want to get me on all fours, do you?"
- "I really want to eat you"
- "Give me some milk first. Pour it all over my face."
She started sucking me in an alternating rhythm, slowly and then quickly. I felt like I was going to cum very soon. While she was sucking me, she looked at me with a naughty expression, like she was in control. What a bitch!! She took everything out of her mouth and then went down quickly with her mouth, swallowing everything. It was wonderful.
When I was almost cumming, she stops, stands up and turns her back to me. She starts to come towards me with her back to me, rests her left hand on my left leg and grabs my cock with her right hand. She starts to pass my cock at the entrance of her pussy and I start to moan a lot feeling her wet. She starts to sit down slowly while my head goes in, when it is all the way inside she sits down hard, leaving me breathless while moaning. I held her waist while she sat down very hard. She started to shake her hips and then I started to stimulate her clitoris while she moved a lot, that's when I started to feel my cock being plunged into her orgasm while she remained static, writhing, she moaned softly while I felt her pussy squeezing my cock and she said she had cum. She gets off of me and lies down next to me on the couch, spreads her legs and with a naughty face calls me with her little finger. That's when I start to suck that wet and swollen pussy, I explore her body, grabbing her breasts.
- "That's it, that's it, suck it. Oh my gosh, stick your fingers in me."
So I suck and masturbate while she tells me what to do, until she cums in my mouth. I get up and look at her and see her eyes half-fallen, as if she were sleepy. And that's when I get on top of her on the couch, kind of clumsy and awkward. She grabs my cock and fits it in her pussy, and I start thrusting deep into her. She holds the back of my neck and my arm tightly and whispers:
- "That's it!! Go on!! Put it in deep, shove it all in that bitch."
We were sweating a lot, I was exhausted, I didn't know how I had resisted for so long and when I was almost cumming I asked her to get on all fours on the couch. When she got on all fours for me and I looked at that pussy all covered in grease, I ran my tongue over it and slowly put my cock in it, I was getting more and more horny with each inch that my cock entered that soaked pussy. Then I decided to thrust it all in at once, she was apparently exhausted, so I alternated between pounding hard and going slowly so as not to cum. Since it was kind of uncomfortable to be in that position, she told me:
- "Take it off, take it off, come underneath and I'll mount you"
I already felt like I couldn't take it anymore, my legs were already wobbly, my body was exhausted but I wanted so much to continue, that was unique for me, but my body was betraying me with each ride that woman gave, how delicious it was to see all that on top of me. We both knew that it was our last position that night, because we didn't have the strength to continue so she did her best. On top of me she started to go up and down with great force, she went up slowly and when my cock was almost coming out of her pussy, she sat down with great force, she moved back and forth while I sucked her breasts, when she started to ride me hard again I started to masturbate her, she started to moan like a bitch while bouncing on top of me
- "I can't take it anymore, Ana. I'm going to cum."
- "Keep on whining just a little longer and I'll go too. Oh my gosh, I'm almost there."
- "I'm going to cum, I can't take it anymore. Where do I cum, please?"
She laughs when I ask where I can cum, and tells me:
- "Cum inside me. Give me milk. Fill me with cum. Come on, cum now, give this bitch milk, come on."
We came frantically. She got off me and sat next to me. I was already dead tired and lay down with my head on her legs. She started to pet me while caressing my balls. Since I was very sweaty, she said I could take a shower at her house. We took a shower together and I even got a blowjob in the shower LOL
After that, we had other affairs, but never like the first one. Nowadays, she only goes to my grandmother's house, my mother and she kind of drifted apart, but we still see each other very often, in the end, we drifted apart too, we maintain a good relationship, but we didn't get back to the friendship we had before, I think she just wanted to have sex LOL
Anyway, guys, that was the story of when I lost my virginity to an older woman. Remember that words can't always express what a special moment like this can represent to us.
Feel free to send me emails, we can exchange experiences, you can tell me what you liked, how I can improve my writing, etc. Feel free to type for me.
I will soon share more of my experiences. Thank you and see you soon!