A Virgin To Half-Virgin 25-Year-Old-Boy

This is a story about a wild night with a woman abroad. This is a real experience and I always get hot when I remember it. I am Kiran, now living in Karnataka, 5’6”, fair colored, 25 years old, slim and a 7” cock.

This is my first story in ISS and excited to write this erotic experience with the sexiest woman I have ever seen. I am writing this story nude and let us start the long journey.

I just moved to this town for the job after graduation and found a rented house The landlady was living in a smaller house attached to mine. The landlady was doing some small renovation in our kitchen and she used to come quite often to our house. She was sweet and my grandmother’s age.

After a few days because of the leniency, she started coming to my home when I was not there. I used to work from 9 to 6. One day I had a bad headache and took off from the work in the afternoon and was sleeping in the living room couch with just my boxers.

For everything there is a reason, you know. I was in my deep sleep and suddenly I heard my land lady’s voice, “Oh god you scared me, I did not know you were in the house. Sorry to barge in without permission.”

Coming back from the deep sleep I said “That’s okay, you need not apologize this is your house. I took off from the office after lunch.” It didn’t bother me much for her uninformed visit because of two reason – (1) she was an older lady and was sweet (2) she had brought her friend Joanne to show my kitchen counter, who looked like an angel to woken up eyes.

Joanne was my neighbor. She was 37 years old and had a teenage daughter. She was working in the sales department of a big furniture shop in the town. Most importantly she was also my neighbor.

We continued the conversation, I was still in my boxers.
Landlady: “Landlady you took off from the work? Are you okay?”
Me: “Just a little headache, I am completely fine now.”

Though I was talking to the landlady, my eyes were on Joanne. She was looking extremely beautiful in her loose cream top and jeans. I love it when I can’t predict the shape of a woman when she wears looser dress. It makes you wonder whether she has bigger boobs or a flat tummy.

Conversation continued.
Landlady: “Ohhh. Let me know if you need any help. Forgot to introduce my friend, Joanne. She lives next to your house on the other side.”

And she explained her profession and why she had brought her here.
Me: “Hi Joanne, nice to meet you. I am Kiran.”

I extended my hand for a handshake. Unknowingly I rubbed my palm to the boxer before the handshake thinking that I am touching an angel, at least let me clean my palm. Joanne whilst a quirked smile: “Hello Kiran. Umm… We are sorry we disturbed your sleep”

All this time I did not know I was just in my boxers. I had never exposed my body to a stranger before. I was like this since my childhood I never used to come out of the room bare body. And I wasn’t sure if Joanne was checking out my body. My body wasn’t that great too. It was slim and little hairy.

Conversation continued.

Me: “No, that’s fine. If you could please excuse me I will put on some clothes.”

Joanne: “That’s fine. You need not.”

Me: “What?”

Joanne: “That’s fine. We are leaving anyhow. You can go back to sleep.”

I was a little sad, that the white angel was leaving and covered it with a poker face.

Me: “Oh. Okay.”

She gave me a hug before leaving. I mean she hugged me while I was in my boxers. It was almost erect to not to poker her. She bid bye and took off with the landlady. I could not sleep as I was thinking about her after she left.

To add to her beauty she was a blonde and had the perfect body with amazing blue eyes. I recollected that hugging moment, that’s when I realized she had that perfect natural boobs too which smoothly pressed against my bare chest.

(Remember she was wearing a loose top because of which I could not anticipate her mere measurements.)

I did not want to fuck her or anything. Of course, you can’t have sex with all the hot woman you meet and that too in a strange city.

Several days passed, I was busy with my work and didn’t actually get time to contact her even though she was my neighbor. Friday morning landlady asked if she could have a barbeque party at my backyard. Yes, my house had the backyard. She told she would bring Joanne. A bell rang in my head and said it was the best idea.

They brought the veggies and some oysters for the party. I was told by my landlady to marinate some chicken and lamb with Indian spices, which I had prepared in the morning before leaving to the office. We had brought wine, both red and white. I preferred red as I had stopped drinking white wine after I had a terrible fever after it in the winter.

They arrived at the party around 7. Joanne was wearing her pink top, of course, it was loose. I loved it again and thought she understands your likes. I hugged both of them. She looked extremely lavishing and smelled great. I praised her that she was looking gorgeous. She complimented back to me that I looked dapper. I was wearing a blue t-shirt with brown trousers.

We started the party. I poured the wine they liked into their glasses and poured red into mine. Fortunately, she preferred red as well. She smelled the marinated chicken and lamb and acknowledged it smelled delicious. We ate some oysters with lemon.

Landlady asked me to get some coal from her house which was right next to my house. Landlady was an expert in preparing the fire for the barbeque. Joanne joined me too. We were told where it was on a shelf in the garage. On our way, we talked about her boyfriend who was an elderly man.

She wasn’t married yet and she had a teenage daughter and more. It was the slowest we could walk. It was the wine which opening her emotions. We had finished a bottle of red wine. We reached the garage and we didn’t search for the coal but talked for a few more minutes about myself, which is not relevant to this story.

After a while, we remember to search for the coal and we found a bag of coal on the shelf. We didn’t have a ladder or stool to reach the bad. All we had in the garage was the landlady’s car, a lawnmower, and a bicycle. We searched for the alternatives for a few minutes.

I suggested her an idea which you all might have anticipated by now. I told her that I would lift her up and she can try to reach the bag. She ironically smiled and suggested an alternative which shook me.

She suggested that she would live me up and I get the bag. She looked strong even though she was of my height and medium built. I accepted the offer. She bent and held my thighs tight and started lifting me up with little difficulty. I did weight around 65kgs.

My crotch was in front of her face. But she wasn’t looking at it, rather she was looking at the bag if I was able to reach it or not. I was dumbstruck what to do next. She asked me to do it fast. I brought back my senses and caught hold of it and dropped it on the floor.

The next few seconds were experienced slowly, very slowly in my mind. She dropped me slowly to the floor. I could sense my thighs brushing against her soft, plump, non-saggy boobs, her flat tummy and my chest pressing her boobs again. It ran very slowly in my mind, just like in any Bollywood movie.

I was already aroused. She was kind of aroused too. I did not feel the courage to kiss her. In my mind, I had not touched the floor yet. After I was dropped to the floor we hugged tightly for a few minutes. She asked me to let us go and attend the party as the poor old landlady was all by herself.

It was 20 minutes almost since we left the party for the coal. We came back to senses and she suddenly kissed my cheek. We smiled and went back to the party. We were teased if we went to the nearby city to get the coal by the landlady. We made up some story instantly that we didn’t find the stool/ladder.

We smiled looking at each other in the corner of the eye. Meanwhile, the landlady has gulped one bottle of white wine completely. We enjoyed chicken, lamb, and veggies. Joanne and I finished one more bottle of red wine. Whilst Joanne was washing some utensils at my home, I cleaned up the mess in the backyard.

Meanwhile, I heard the poor old landlady snore. It was almost 9:30 pm. I gave my shoulder, walked her home into her bedroom and put her in bed. I didn’t have more wine. I asked if she was okay with the beer. She suggested if we could share one beer. I was extremely okay with it.

We talked, watched tv and she told that I could be her new best friend. It was late and I suggested her to stay at my place, even though she was right next to mine. She needed her sleeping clothes and I gave her my brown loose shirt and a night pant.

We were high already. She asked me to go out of my own room so that she could change. But she didn’t close the door. Whilst I was going out of my room, she started changing immediately. I stopped to look at her. She removed her pink top and black bra in front of me.

She had the most amazing pair of boobs, it was 45-55 boobs, she had the pink nipples, perfectly sized areolas and it was bra which she removed was perfectly covering these gems. She removed her thongs, her pussy looked shiny, maybe it was wet and it was neatly shaved. And she put on my night pants.

She needed to pee and went inside my bathroom. She did not close the door. I saw her buttock whilst it was perfect not too big, not too small. Just perfect. I heard her pee, it was extremely erotic. And we went back to the living room to watch tv.

I acknowledge that she was strong enough to lift me at the garage. She told she runs daily and maintains the healthy diet. She challenged that if we fight she would win. I grinned. Suddenly she punched my left biceps for grinning. It was a good punch. We suddenly started fighting and rolled to the floor next. Nothing hot here.

But I could miss seeing her perfect boobs jiggle while fighting. After this moment she took my arms and placed them on her boobs. I was astonished to see my hands on her softest boobs. I looked her in the eye and kissed her. We kissed for a while. My hands still on her boobs over my shirt.

Its time for me to show how strong I was, I lifted her in my arms and still kissing and took her to the room where she changed. Her clothes were on my bed. We kissed for a very long time. Now my hands were inside her shirt and were caressing her boobs slowly. I did not rush. She removed my shirt, I removed hers.

We removed our bottoms. Fortunately, I was wearing the same boxer as she watched me first. She recognized that and acknowledged it too. It was hot. She removed those boxers and saw the penis which was extremely hard. (Veins were literally popping out and I was a little wet too).

She whispered it was biggest she ever saw and started to suck my virgin cock. I told her I was a virgin. And she loved that fact that this was my first sex. She sucked till I ejaculated in her mouth. I lied her down and sucked her boobs for a long time. Also, I started inserting fingers into her pussy. Her pussy was tight and juicy. She whispered to suck her pussy.

I sucked, played with her clitoris in my left hand and played with left nipples in my right hand. She moaned very loudly as she was loving every moment of it. She came and squirted on my face. And she was satisfied. Meanwhile, my dick was up and started fucking her slowly in the missionary position after wearing the condom.

Since I was a virgin this was the first time I fucked a woman. We fucked for some time and she remembered that she was with a 25-year-old boy and she was happily committed asked me to stop in the middle. What she felt I sensed it. I removed the condom and I slept beside her. She asked sorry that she couldn’t do it and kissed me. After some time she saw my bare cock and asked her to fuck her again.

I had to put a new condom again. She fucked me in the cowgirl position. She was very aroused and moaning very loudly. She was going at a very high speed and lost control. The old thought came to her again and she whispered to not to continue and asked me to sleep on the sofa outside the door.

She told she could not control if I was in the same room. I removed the second condom and slept on the sofa. I was not sad. I got a lot more than what I expected. I had remembered that she had to leave early. So she had an alarm at 6 am. She probably felt bad when she woke up. She came out of the room and saw me.

She removed my boxer and woke my cock, gave me a perfect blowjob. She played with my balls, she pinched my nipples and squeezed my butt. I remember when I woke up she was deepthroating me. After 20 minutes, I told her that I was cumming. She took everything in and swallowed without leaving a drop.

She kissed me and slept in the same blanket for 10 minutes. We cuddled. I warmed her boobs by cupping both of them. She whispered “sorry” and left to her home in my shirt and night pant. This is how I remained a half-virgin.

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