My first experience, losing my V Card to a 38year old female corporate boss

NSFWNo Regrets

Been reading through the sub for a while and have been in two minds to post about my sexperiences, the rollercoast ride of people and the way it has happened, so decided to go for it and start from the first. Here goes.

Me, at that point I was 20, was working at my 2nd job. Banking Associate at a prominent bank at Col 3. Right after AL and my first job had like two flings, never went inside them with both of them, only kissing, squeezing, fingers, i suck her she suck me and both broke up. So was about good time to get out the being a virgin and you know was one fine bored day on the bed night time, scrolling on FB.

On the recommendations, I saw a profile, immediately the profile picture caught my eye, a woman, curly hair, beautiful eyes, not slim not fat, sitting on a chair, wearing like a floral frock thingy with the top ending like a tube top, no straps, you could literally see those big ones sitting on that tube top and the cleavage being so tempting showing the curves up since they were BIGG. Well yeah so definitely tempted, me being a young desperate, sent a request.

Was drooling over the picture (naturally I have a thing for curly hair girls) and it got accepted.

I started the convo, didnt say Hi or anything I just said your eyes look beautiful and she responded saying not even Hi but flirting already and we were going on chatting for a while. During that time I learnt that she works literally walking distance from my current workplace, she lives in Ratmalana while I was in Mount, she is one of the Senior Managers at the company - one of the conglomerate giants in SL atm. Me the horny self was more interested to get into intimacy or sexting with her since I didnt want to be like formal much with her and Im too damn small for a relationship with her being almost twice my age. So I learnt that she isnt married, had a bad breakup after getting engaged and all.

We ended the night and I went asleep hard. Next day, good mornings were exchanged via chat and that same day we decided to meet more like she was too damn straight with me as she got to know I travel by Bus, she said me to come to her office so she can drop me as she takes the tuk daily. I didnt know where this was going, end of my work, I reached her office, huge af. She guided me to her cubicle on the chat, literally commanding on the chat, we hadnt shared numbers yet. So yeah I went up the lift, went inside, walked left and right and there I was in her cubicle. She was wearing an office shirt and pants, brownish curly hair. When she stood, I saw her figure, damn she was shorter than me, bit on the fair side, we shook hands, she made me sit on her desk saying she needs about 15 minutes to finish work. The moment she sat on the desk, that shirt became sooo stretchy with her big curvy boobs against the shirt. I tried to be decent. So nada nada nada, she took way more than 15 minutes and it became about 7ish and even one old uncle came said bye and left leaving just me and her in the floor. She got done in a few minutes and she said come ill show you around she showed places and entered the kitchen area, with a balcony behind. When we stood there, she bought up the question, so how am i now? I was like uh? she said on the chat you said eyes are beautiful hair is lovely dress is lovely and all that now that you see me in real tell me is the eye really thaat beautiful and she took a step closer me like so close looked me in the eye, I am about 5.11 in height, broad shoulders, muscles at right places, and have inherited my dads genes, dad is a morrocan so I also have one packing down there thats over 7inches and thick. She was tall too she was looking at me while my eyesight was looking down into her eyes, in a few seconds it was like kiss her rn feel. I felt awkward natural instint looked up to see if there was cameras she said no cameras dont worry then i said yeah its beautiful and casually leaned a bit and touched my hip and gave a small hug, light one, good enough i felt her boobs on me, soft and before i could process anything she step away and said dont worry i wont do anything to you looking at my nervous face, stepped away smiling while i stood there like a donkey.

Nervous but got hard in between and I kinda felt like a little precum came when this happened. I saw that she saw my bulge as I only were loose boxers for freedom for my fella and she just went and i followed her to her cubicle. she then booked a tuk, she switched lights off and we came down awkward me kept silent we got into the tuk, we were again talking and this time I made a move, kept my hand over her hand while we talking in the gap between us, her hands were on the seat. she kept talking i kept talking and one point she stopped and was like you know what we are doing and pointed at the hands from the eyes, i said yeah, turned it, fully held her hands fingers between finger and smiled, she pulled a bit i went closer she came closer and naturally since im tall i had to put my hand over her shoulder while holding hands so having my elbow and up right on top of her boobs, I ofcourse was purposely keeping it more there while i was getting hard as well. Again she was taking more on the lead being the mature person this was all very new and nervous for me being just 20.

Suddenly she stopped talking and was like what are we actually doing, we just met a few hours ago, already holding hands and soo close in the tuk, i just said idk but this feels like its right and I love it, she said yeah this feels good for me too but you are just 20 and she was going to say something but i just leaned in and kissed and came back. she looked at me and i looked at her again, we both wanted it, we kissed again for a few seconds harder this time desperately, once it was done, i asked her, why does this feel so good. She looked front and thought for a second and said, idk but I want to find out. This happened while we passed Dehiwala and she told for some road name and to drop us there I was visibly confused, until we came there we here doing more kisses obv and it sylvester place it was, we got down, there was a room place, she went in, i followed, nervous and scared, never have been to a room, scared whats going to happen though I want it so bad. She paid, we went into a room locked door and immediately hugged and kissed as if there was no tomorrow. I removed my shirt, she removed hers, and she sat on the bed, I was looking at that huge boobs she has she was wearing one of those round shaped bra that covers like the entire boob they were big ill tell ya, she sat down i went closer, she pulled me closer, removed my belt, unbuckled my trousers, big fella curious, she touching it and looked at me keeping eye contact while she pulled my boxers, while lookin at my eye, as she removed, she being so close to my D, it knocked on her chin like she smiled she kept looking at me, still not even holding my dick or touching it hands on the side of my hip eyes looking at me, i was idk what to do just standing there, while she kept looking at my she moved her face a little to get my D around her mouth, slowly opened her mouth and took the tip in and started sucking it up and down still while looking at my eye slowly but steadily, slowly she was trying to take more in and then she wasnt able to take it whole then she let my eyes and looked down pulled out of her mouth and was like looking at me said lokui she went onto suck me for few minutes, not for a long time at all because we both wanted something else totally it was feeling so good, was holding her head trying to push but she just stopped me, pushed me away abit, got up removed her pants, undie and lied back on the bed with legs spread and knees folded up with the bra on and said come find it out.

That was when it hit me, like i was commiting a sin of fraud and i just took a step back nervous and scared, she sat up asked why i said no i have never done this and feel its a sin and wrong she just did the hair flip and said just come and pulled my from my hip onto her, not aggressively you know just gently i also fell ontop of her and with the fall in went my D, the front bit, it felt soo slipper and wet, i started to thrust in about the 3rd thrust like most of the dick was inside her, it was feeling super warm and comfy inside her almost as if my dick was getting a warm water gel massage on its own, kept thrusting and was kissing and you know it was my first time right so after I lasted only like about 10 to 15 thrusts and with the expressions of my face and my moan she figured out im going to cum she tightened her leg grip on my hip, I told her shyly im going to cum while thrusting she didnt make a face or seem dissapointed she just leaned forward and kissed me and held me tightly with her legs and i understood the signal and did the final few thrusts hard and deep and then when i came naturally i broke the kiss because it feel soo damn good for the first time and my moans were coming out and came inside of her. All of this from entering the room to cum happened in like less than 10 minutes, i leaned over her, she smiled I smiled this time kissed her, while still inside her and while kssing my hands went down her boobs and pulled down the strap and pulled them out, big brown boobs infront of my face i sucked them all and played with them and then went to her tummy playing wit her navel sucking licking them and slowly went down to her pussy. Wet, I played a little by blowing warm air on it and sucking on the sides instead of the pussy lips and then I started licking. Generally ive gotten feedback from previous girls that my tongue game is good, so with that confidence, I started giving it to her, tongue inside rolling deep and suck it all she held my head moaning and while iwas continuously busy with my tongue I can feel her thighs tightning on my head bring them closer little by little with her hand on my head and i think she was about to reach her peak but she held my head and pushed it away and sat up and immediately she was like are you really 20, i smiled pushed her back and went inside her one more time. This time i went in confidently like a big pornstar and went in and out of her and again, didnt last more than about 15 to 20 thrusts and I came again. This time ofcourse she smiled poddak like funnily and we kissed again and stayed for a while, she said ill ask you a question, I said ok, she said tell me how was your first time but dont tell me now, after you go home when you are about to sleep at that time message me and tell me about it.
We then got dressed , she dropped me at my lane top and went at that point only exchanged numbers and we had this thing going on meeting just to suck and fuck for about 1 year until she got married and left the country.

Thats it peeps, end of story, regardless of this being my first time, she really opened a tap of sexperiences for me from girls from office, bank customer, sister of my ex, etc etc. Would love to share them all one by one but solely based on how you people react to reading long ass stories.

Posted Jun 3, 2026, 11:49 AM UTC

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