A boy named Deepa

I met one of my friend from school days by chance and got closer to him and his mom

When I was in school, Deepak was one of my class mates. A note able thing about him was that where most of the boys were growing fast he was growing slow. Then his father died and his mom took him to another city. I lost contact with him. A few years later I went to same city for university education. Deepak was in same university and it was a pleasure to meet him again. He was still short and slim and his face lacked manliness. I got admission in class but not in hostel. I was put on a waiting list.

I sought his help for a temporary stay. Knowing I can’t afford a hotel, he offered me to stay in his house until I found a proper accommodation. I was reluctant initially but then he took me to his mom who welcomed me. She was a good looking lady of 42, working in a firm as an account officer. She knew me already so she invited me to live with them. That’s how I came to live with Deepak and his mom. They had a four bedroom house and I was given a room with a study table and a computer. A double bed was already there. It was enough for me. Although Deepak was not in my faculty but we used to go and return together often. In the house we used to take tea and meals together and chat in spare time.

I wanted to avoid disturbing the privacy of Deepak and his mom so I used to spent more and more time in my room or outside. The twist in story came when one night I was watching porn on computer and jerking myself slowly. I forget to lock the door and in came Deepak suddenly. I tried to hide my erection and close the computer. I was feeling very embarrassed but Deepak just smiled. The computer screen wasn’t facing him, so he didn’t see what I was watching. He only saw me putting my cock back in my pajamas. He said he had no complaint as long as it remains a secret from his mom. I thanked him for not minding.

The incident was forgotten for few days. After living in his home I realised that Deepak was very close to his mom. As she was a working woman, he used to help her a lot in house chores like washing dishes and cloths. Occasionally he used to cook food too. First time I ate food cooked by him I said, “Wonderful buddy, You really can cook”.

The next incident took place when one day we returned from university in rain. Our dresses got wet but house was locked. Deepak forget to take his keys with him and his mom was still in office. He requested next door neighbours to let us use their roof. Through their roof we reached our roof and then entered the house. I had the key of my room with me but his keys were locked in his room.

I went to change in my room whereas he went to search for some dry cloths in a outside washroom. I changed to dry cloths and was astonished when he appeared in my room with tea. He was wearing black leggings with a blue lady jacket. These were tight fit on him and clearly belonged to his mom.

“Deepak… you??” I was shocked.

He smiled and handed over me the tea. While sipping tea he told me that there was no dress of him in sight so he used his mother’s cloths from the basket. I said you could have borrowed my dress easily.

“Your dress will be loose on me and its only temporary. Soon mom will return and I will wear my cloths”.

“You look a girl in them buddy and a sexy one” I said to him and winked.

He blushed and said, “Please don’t tell this to anyone in university.”

I however, felt a slight movement in my cock. Later when his mom returned he was still in same dress. I was again shocked when she said nothing bad to him. He was in men dressing when we met at dinner. As we talked about the rains and keys his mom laughed and told me that I should not tell anyone about her son’s habit of wearing her cloths.

“It appears he wear them often.” I said.

“Not often but sometimes he gets bore and like to wear my dress and look like a girl.” She laughed when telling me this and I thought that she is as weird as her son.

Now his secret revealed he was more open with me. He admitted that he use to drink sometimes and wont mind if I do the same. So we started sharing bear on week ends.

One weekend he stayed with me to watch a movie on Netflix and drink some bear. Frankly the story line was boring and I was about to doze off when a hot bed scene appeared on screen. That was the only part of the movie that interested me. The actress was almost naked and was kissing her lover madly. Her bulging tits and bare belly button gave me a hard-on. I had an urge to jerk off but controlled due to the presence of Deepak. He perhaps realised that. Very soon I felt his hand on my crotch. He must have noticed how turned on I was. He rubbed my crotch and slowly slid his hand inside my shorts. By feeling his hand on my cock I felt in heaven. That was like a scene from fantasies. Call it an effect of the bear or anything but my eyes got closed in pleasure. I let him play with my cock. As I moaned his strokes on my cock got faster. He was jerking me off like an expert. I failed to hold it in anymore, so I groaned softly and ejaculated. As I moved to washroom, Deepak moved out of my room.

Now it was clear that my friend was gay but in my mind there was no question to fuck another guy. At least that’s what I told myself. Only the next day he came in my room and said that faucet in his bathroom was not working proper so he want to take a shower in my bathroom. I said ‘ok’ and he moved to my bathroom. First he gave me a strange look and then let the bathroom door remain open. I saw him getting undressed and then showering nude. When he bent to pick a soap he kept his buttocks towards me. A look at his girlish hips turned me on. I forgot my decision to avoid gay sex.

I felt a fire rising inside me. I wanted to have him then and there. I dropped my dress and stood behind him. My erect penis poked his ass crack suddenly. I hugged him from behind and kissed the nape of his neck. There was no resistence from him and no foreplay from me. I pushed him down over the floor on all fours. I picked the bath jel and rubbed it over my penis. When I lined my cock head on his puckered butthole all he said was, “Please be gentle,”

My finger went inside the his soft butt hole, and he cried. But even in his cries, he sounded like a girl. Kneeling properly, I replaced my finger with my cock. I
opened the his hole wide with fingers and thrust my cock in. He screamed and craned his neck around, his hair sticking to his face as the water from the shower was constantly beating down on us.

“It hurts, friend,” Deepak cried, biting his lips.

As my cock moved halfway in, I thrust it in deeper, to tear open his hole some more. Deepak (later Deepa) was almost crying and begging me to stop.

I slightly took my cock out, gave another thrust, and he yelped. This time it hit deeper, and his body was pushed forward. He held onto the toilet for support.
By Pushing and pulling I started a ruthless fucking. I could feel his tight hole closing around me, but I just pushed harder. The first few minutes were agony for him as He was hugging the toilet, crying, pleading. I was relentless. Hitting deeper and deeper. Soon Deepak began to release some sweet moans. “Uhhh… ahhh… oh god.” He was still hugging the toilet, and his knees scraped forward with every thrust.

“Oh, yes. Harder, ahhh, harder, please,” he said

Clearly I was not his first and he seduced me to this. His face pressed against the toilet rim, he sang a symphony of moans and grunts.

“Call me Deepa,” he begged.

I spanked his bubble butt. That’s when I felt a warmth inside me. Loads after loads of my semen were dumped inside him. At the same time, he himself ejaculated all over the floor, without even once touching his cock. While I was cumming I kept thrusting until everything came to calm.

Once finished we cleaned our bodies and moved nude to bedroom. Once we were on bed he then stuck his tongue inside my mouth, and I accepted it gladly. Our warm lips smushed together, and our saliva mixed around our intertwined tongues.

Then I asked him why he turned gay and he told me his story. He said, for sometime I realised that my feeling were not like other boys. One day I went to a nearby shop for purchasing something. As I was returning a man pulled me to a corner and started kissing. I was in shock and confused state. But at the same time, I liked it a lot. After a few minutes, I pushed him away and ran home.

Then I realised I like to be girl. In secret I started to wear my mom’s inners while sleeping or wrapped her cloths on my body. By doing this I always had a hard-on. But I never thought I like to have sex with other men. This all changed when one of my cousin came to visit us. He was many years elder to me and married. I have a lot of respect for him. One day he came home drunk. Mom slept in her room and he in mine. While sleeping I felt someone pressing my waist. My t-shirt was lifted and someone playing with my hips. It was him, my cousin. He slid his hand inside my shorts and caressed my ass. He was rubbing the entrance with his fingers softly. I felt a tingling sensation in my stomach. I didn’t know what to do. But something inside me wants to hold his cock and suck it.

“Not so hard please. I’m your cousin Deepak.” I said,

“No. You’re my goddess Deepa.” he said

My heart throbbed as he placed his cock at the entrance of my anus and pushed slowly. I gasped. It’s like a rod entering. He is giving small strokes and entered fully. I screamed. At first in pain and then in pleasure. Every time I begged him to go slow, his thrusts would come faster and hit deeper. Finally he flooded my butthole with his cum.

As Deepa (Deepak) told me his story I was rock hard again. This time I put my large body over his petite body and rubbed my large cock on his tiny one. I kissed his neck and the earlobes, and he was more submissive than a girl. My hands explored his body by rubbing his back and pressing his buttocks. We twisted and rolled on the bed, each with our arms wrapped around the other. I feasted on his nipples by chewing and biting them. His boobs were not big but he had no hair on them.

I kissed her there a few times caressing her thighs and her butt. Deepa returned my kiss happily, by running a hand through my thick hair. I put my tongue in her ass crack. How do I describe her reaction? She was ecstatically moaning and I sunk my tongue even deeper into her crack. I was salivating like a hungry dog. I could feel my saliva wet her crack drenching it.

In that state, I penetrated her. She extended her arm on my back and pressed against my butt saying, “Don’t let it come out.”

I started thrusting her. It was so tight and warm inside, her asshole squeezing against my shaft. Lying lip-locked with tongues tied, I thrust again. In response her legs scissored around my waist, pleading me, not to stop.

“Make me your wife or whore!” she said.

Hearing that I pumped load after load of my cum inside Deepa, which flooded her insides and then flowed out of her gaping butthole.

Cutting some details I admit that a new bond was established between us. In his soul he was already Deepa now he became Deepa in appearence too. In secret he became my wife. He now wore sarees and skirts when he was with me — sometimes, he put false nails, lipstick, mascara, even a wig to look like a woman. Then one day his mom caught us in act.At first she was angry then she said to me that I should help her son rather then abusing him.

When I asked how I can help him turn into a normal man. She told me an interesting story. She said one of her maternal uncle was similar to her son in his sex orientation. He refused to marry so his mom took him under her charge. She trained him with the help of some other women. They used to fuck men in his presence. It stimulated him and once he got erect they used to fuck him. Now he is married and father of two.

“Ok auntie I can fuck a woman in his presence but who will be the woman?” I asked

“Me, who else silly.” She replied while blushing

I don’t know whether she was interested in me like her son or she really wanted to reform her son. She was very tempting despite being mature. In her cloths, her curves were very obvious. The way she smiled and played with her hair made it feel like she was flirting with me.

Next night all of us gathered in her room which smelled of her feminity. We all undressed and moved to same bed. Her breasts felt good in my hands, as they were big and firm. She had long dark nipples, which I eagerly sucked, soon her son was sucking on my cock. I couldn’t believe how horny they were making me. With her legs spread wide, I leaned forward to caress the tender skin of her legs; I slowly rubbed through the lips, teasing her senses. I pumped the head in and out, groaning from the exquisite sensation of her pussy’s grasp.

She quivered with hunger, and moaned, “Oh honey! I’m ready…so ready…please…please…please, fuck me!”

She was dripping wet, aching to be satisfied, as I pushed more inside. Her eyes never left mine, as she rolled her hips up to meet me. Her eyes grew, her legs open wider and her moans got louder, “Ohhhh God! Please…mmmmm…please, gimme that dick…it’s good…all that thick…thick…yeah…thick dick…yeah… yeah, Feels good…good…uhhhh…uhhhh…uhhhh.”

My hands gripped her hips, pulling her into me and pushing my girth deeper. I was all in before pumping with smaller thrusts, to start, pulling out a few inches and pushing back in.She begged for more, “Gimme… gimme all …uhhhh…. uhhhh… mmmm… my pussy’s yours… all yours… .”

Meanwhile Deepak got erect by seeing his mom getting fucked by his friend. His cock was not large but it was erect. He was as excited as she was and he was puming his cock. I was fucking his mother, closer and closer, to orgasm; her other hand slapped hard and dug into the cushion, while pleasure overwhelmed her body. She told me to fuck her pussy without worry as she was on the pill. I quickly Started Cumming filling up her cunt with cum.

As I moved away from her she quickly cleaned her pussy and pulled her naked son over her body. I watched them and felt getting hot. She told me that her son is loosing his hardness so I should help him regain it. I rubbed his balls and fingered his bum Finding a lube tube, I buttered up Deepak’s ass, I slowly entered his ass and slowly fucked him, his ass was tight and the pleasure was intense. His hardness came back.

“That’s it … it’s working … it’s good … oh yeah” his mother told me.

My fate brought me to a house with two women, both of whom are loving me and I am loving them.

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