Sara – Part 1 (My First Boobs Experience)

I am a 35-year regular Indian man. I am 5’11” tall, decent looking and well-educated. I used to be lean and fit but I have gained some weight due to my love for whiskey, good food and lack of exercise. I have a normal straight penis measuring over 5 inches.

This is my the story of my first ever experience as a teenager. I was in class 12. I have had girlfriends in the past, but had never moved past kissing or making out passionately.

This story is about my girlfriend at the time. We will call her Sara (name changed as I don’t want to even remotely violate anyone’s privacy, especially since we are still good friends).

Sara is good looking. She was considered hot by my friends. In fact, 2 of my friends really had the hots for her. As a short 5-foot girl, she had a petite girl’s body (she is filled in a little now, but she is still petite).

I don’t remember her stats now but she had small breasts just big enough to fill my hands. She had a flat stomach with a bellybutton pierced-ring that looked hot in t-shirts and a small yet well-rounded butt that suited her size. She used to dress well and casually outside and wear t-shirts and pajamas at home.

Sara was a few months older than me. We lived in the same building and had the same friends. She was a friend too. I was dating someone else at the time when we met. After my break up with my last girlfriend, I was a little distracted and had trouble sleeping (teeny over emotions).

Sara saw that I was disturbed highly and wasn’t handling things well. So she asked me to take a walk with her and talk with her. She asked me why am I so upset. I told her that I really liked my ex-girlfriend.

The truth was my ex-girlfriend was extremely pretty but one of those girls who is totally into looks and appearances and makeup. She was a surface girl without any depth, but then again, we were kids. She is a social worker now but the conversations are still pretty superficial.

I wasn’t really into her, she realized it and we called it quits. Being the first breakup, I didn’t know how to handle my emotions.

Sara: So what, I have had boyfriends. You will have more girlfriends. Why are you behaving as if it is the end of the world? You are a good looking boy.
Me: Thanks.

Sara: I am not kidding, you are a good looking boy, you are smart and intelligent. You will have plenty of girls later, you will see.
Me: I am not insecure about that, I am just feeling low.

Sara: Dude, listen. There is no reason to feel low. You are going to be fine.

(She started a little friendly flirting to make me feel better)

Sara: I would totally be your girl if we weren’t such good friends.

We both laughed. The conversation became normal.

Over the next few weeks, we hang out a lot in the evenings. My friend asked me if something was happening but I told him nothing was. We actually were just friends.

Then he asked, “Well, she told my girl that she really likes you. But she is the kind of girl who won’t make the first move”.

I thought he was kidding and told him to stop pulling my leg. He said he was serious and his girlfriend told him.

I thought about it, but I didn’t want to jeopardize our friendship so didn’t act on it. Sara was cute and hot, why risk it with so many common friends.

One day, Sara and I were chilling in her room listening to some music. There were 2 beds, lined up in L-shape along the wall, to give the room more open space in between.

Delhi weather in November used to be chilly and Sara was wearing a shawl with t-shirt and tracks underneath. The room had a heater, so the shawl was pretty loose around her neck.

Lying if different beds, with our heads close together in the L-shape, I saw what every 18-year-old raging hormones guy likes. Her shawl was loose, so was her t-shirt. But I could see deep into her t-shirt because of the way she was lying down. I could see a LOT of her breasts because she wasn’t wearing any bra (she was home covered in a shawl).

Sara was saying something but I lost track. I was a young guy seeing breasts for the first time. I had seen porn and a lot of Playboy magazines, but this was the first time I saw boobs in front of me.

Sara: …

I was looking at her boobs and not knowing what she was saying.

Sara: P! I asked you a question!
Me: Yes yes. (Still looking at her breasts, mesmerized).

Sara thought something was off and looked at me. She saw I was staring at her boobs and realized I could see most of them because of the way she was lying.

Sara: ….

I was still not paying attention to what she was saying.

Sara (poking me with her finger): I am talking to you, dumb ass. Done ogling?
Me (coming back to my senses): Oh sorry. (Awkwardly) I didn’t mean to stare.

Sara (adjusting her t-shirt properly): I understood you were distracted when I asked you what you wanted to eat and you replied, “Yes yes.”

Me: Sorry. Just seeing breasts for the first time in person. I have seen them in porn and all and tons of cleavage, but never so much boobs. I got lost.
Sara: and turned on (pointing to my crotch area of my tracks which had a tent coming up) Ha ha. Nice to see.

Me: Oh sorry ya. (Turning and adjusting)
Sara: Don’t apologize. It is natural..(pause) ..and a little flattering.

Me: Flattering?
Sara: Oh, come on. I know you know I have a crush on you. S (my friend’s girlfriend) told me he told you. Good to know I turn you on.

Me: You are kidding me. I get turned on just by looking at you walk from behind.
Sara: Oh really.. So you look at my butt when I am walking.

Me: And apparently your boobs too.
Sara (laughing): Ha. What else about me turns you on?

Me: Your lips. I really like your lips. They look beautiful.
Sara: You mean these turn you on?

She leaned forward and started kissing me – pecks in the start and then a smooch. We smooched for about 2 minutes with only lips. Then I felt her tongue parting my lips and entering my mouth. That was an amazing feeling! That Adam Sandler movie was right, first kisses are truly amazing.

We both started to sit up, all the while with our tongues fighting and our lips locked. I moved and sat next to her. I didn’t want to kill the moment nor make her awkward or anything. So, I rested my right hand on her thin sexy waist and the left behind her back.

We were kissing for a good 10-12 minutes when we heard someone approaching. So we quickly parted and sat on separate beds. The door opened and it was her younger brother asking what we wanted to eat?

Sara: Nothing. We are going to poojas. Everyone is coming there and we will be ordering pizzas. (She cooked this story up instantly) We were just going to leave. Tell ma not to cook for us. Let’s go.

We left. Getting into the lift,

Me: I really want to kiss you.
Sara: Me too. Think of where we can go.

I remembered no one goes to the roof barring the plumber and he would have gone home by now. So, we went to the top floor, got out of the lift and went upstairs towards the roof. It was locked. Perfect.

We just sat on the second last stair landing. This way we could make our escape in case someone came.

The moment we sat, we started making out passionately. I held her face with my left hand and held her waist with my right. We were kissing fully. Sara removed her shawl and kept it next to us, all the while kissing. I was thinking this could be my green light to take things further.

I waited for a few moments (while our tongues were exploring each other’s mouths) and then decided to test the waters. I put my right hand underneath her t-shirt and onto her sexy back. The moment she felt my hand, she took a deep breath and kept kissing.

I was glad she didn’t pull away or get awkward. I started exploring her back. It was so sexy.

For the next 5-10 minutes, we kept kissing while my right hand was exploring her back. My dick was hard and tenting my tracks. I took my hands a little further (remember, she was braless as she was home in a shawl) and felt some side-boob. She jerked a little the second I touched the side of her boob but she kept smooching me.

I took my left hand and slowly entered the top of her t-shirt to cup her right breast. The moment I did that, Sara let out a moan in my mouth. I squeezed it gently.

God! It felt like heaven. It was the FIRST time in my life I was touching and feeling a girl’s breasts. It was small, just enough to fill my hand, soft yet very firm. I kept kissing her all the while squeezing her boob.

Then I pulled out my hand, opened the only 2 buttons on her top so that I could access her other boob comfortably as well. I didn’t break the kiss and she started moaning as I was feeling her breasts and squeezing then nicely.

With both my hands in front of her shirt, I was massaging her boobs while she was kissing me as if there was no tomorrow.

Then I moved my left hand to push down the t-shirt and took her boob out and kept squeezing it hard. I broke the kiss and moved to licking her neck downwards. She kept moaning “Aahhhh.. ahhhhhh.. ahhhhh.. sssssss..ahhhhhh.”

I was getting very excited. This would be the first time I would be kissing a boob.

I was kissing her upper part of the boob while cupping the lower and squeezing the other breast with my free hand.

I really wanted to see enjoy myself so I took my time and started licking and flicking her nipple with my tongue. With the first flick, she instantly grabbed my head and moaned. She had dark nipples and areolas.

Sara: God! Ahhhhhh.. You sure you haven’t licked boobs before? Sure doesn’t feel like it.

Me (in between licking): Never. This is the first time. They are beautiful.

Saying this, I took her boob in my mouth fully, started sucking hard while squeezing her other boob mercilessly with my hand. She kept moaning.

I did this for a minute and then bite into her boob.

Sara: Ahhh.. Ouch! Easy, tiger. They are all yours.

I kept sucking and biting her breasts. Sara’s hand moved to my hard on over my tracks. She started to feel my dick from the top and rubbing it lightly.

I moved in such a manner that I was on her and our crotches were touching. She kept running my hard on over the fabric. I took this as a sign and started moving my hand lower towards her pantie. The moment I entered her pantie, I could feel a little pubic hair.

Suddenly, I felt her hand move from my hard on onto my hand entering her pantie.

Sara: Don’t go there. Can we slow down a little? I want to take things a little slow.

She looked so cute and innocent.

Me: Sure.

I started to pull away, thinking she wanted to cool things off.

Sara grabbed my hair behind my head.

Sara: I said slow down as in let’s not make love today. I didn’t ask you to stop.

Saying this, she pulled me to herself, shoved her tongue into my mouth, bite my lower lip a little, grabbed my hand and put it on her right boob and squeezed. She also positioned my crotch over her pussy area.

We kissed passionately, rubbing my penis over her crotch and for the next hour, we just ate each other’s face while I kept sucking her breasts also.

Hope you liked my first boob experience. In case of any feedback and comments, I can be reached on [email protected]