How I Lost My Virginity And Became A “gigolo” At The Same Time - REPOSTED

I was a 15 yrs old kid, and had just arrived on December 22nd with my entire family to the US and, needless to say, we were broke. Immediately, my parent rented a 2 bedroom apartment for the six of us in Queens.  We moved in with nothing but some old clothes we brought with us from our homeland.  The super of the building had to give my parents a used twin size bed that otherwise would have been thrown out in the trash, and for us, the kids, a large carpet that was to be used as a communal bed.  There we were, four kids, I was 15 yrs old at the time; my sister was 13, my brother 7, and my younger sisters 5 yrs old, sleeping on the floor.
A week later, my parent realized they were going to have problems maintaining our basic cost of living, so my dad decided to sub-rent the apartment to his two female cousins who also had just arrived to this country, until our situation and theirs became stable.  We called my dad’s cousins, behind their backs of course, “Las Chiquitas” (“the petite ones”). They were in their early 30’s and shorter than 5 feet; both were married; however one of them was alone. When they moved in, the Chiquita with the husband was accommodated on the sofa-bed in the living room and the younger “Chiquita” moved in to sleep with us, on the large carpet… next to me, with a separate blanket dividing us.
At first, I was too depressed to think about anything other than my own misery.  I was not interested in having friends or a girlfriend.  I remember that all I wanted was to sleep.  Although, I had discovered ************ when I was 11 yrs old, and became a daily habit, I didn’t have it in me to continue with that pleasant activity.  On top of that, I didn’t know English, I looked way younger for my age, I was short and awkward looking. Hormones hadn’t kicked in yet, I guess.
Things started to change just around months later. One winter morning, just at dusk, while we all slept, I turned around and caught “la Chiquita” standing fresh out of the shower in a corner of the semi-dark bedroom.  She had a towel wrapped around her body with the loose knot right above the breasts.  She was juggling between trying to pull up her panties, covering her damp body with the towel and not making any noise, all while standing up.  I pretended to be asleep, but I covered my head with the blanket to keep on watching her.  When she pulled up her panties, to my surprise, she let the towel drop to the floor.  It was the first time I was looking at an almost naked woman in flesh.  The silhouette of her body stunned me.  She was short, had skinny, but athletic genes, perky small breasts, a narrow waist when compared with her hips.  Her small frame gave her body the youthful appearance of a teenage girl and since she had never been pregnant, her abdomen was intact, no pouch, and no belly fat at all.  I was mesmerized.  A feeling I thought I lost began to emerge again, and my brain began to send signals to my penis again, and it filled with blood and the sensation of having its head rub against the fabric of my briefs returned, and I received it with relief.  A desire to keep on living also returned to my soul.
From then on, I became obsessed with her.  I would spy her every move.  At 6:30 am, La Chiquita would wake up and go to take a shower. At 6:40, she would come out of the shower to begin dressing, At 6:50, she’d be ready to leave.  At 6:55, she would leave to work.  At 7:00, I’d wake up, walk to her closet, open it, and get her just washed pair of panties from the hanger she usually let to dry next to the wet towel. At 7:11, I’d go into the bathroom, pull down the toilet lid, smell her panties, lay them neatly on top of the lid, pull down my boxers and jerk off.  I’d *** just past 7:12, all over the panties, specially around the crotch area, then I’d wipe the rest of the ***** off my ****, wash her panties again, go back to her closet, put the panties back on the hanger, next to the towel, and then, go to sleep again.  At 8:30, I’d wake up to go to school.  All day I would daydream about la Chiquita.  Many times, after school, I’d go back to her closet again to grab another piece of her clothing to jerk off.
The nights became unbearable. Having her sleep right next to me was just making me mad.  I was so desperate I had to do something.  One night, while we all were sleeping, I pretended to “accidentally” get under her covers.  At first, I would just pretend to hug her “innocently”. However, one horny night, I started to spoon her tight and grope her body.  After several nights of gently touching her, I became more comfortable, and I wanted more.  I decided to go for her breasts.  It took some courage, but I got there.  I was afraid she’d wake up, but apparently she was a “heavy sleeper.”  I would just grab them and gently massage them, until she would move or twitch, then I’d immediately remove my hand down to the belly really fast, hoping I wouldn’t get caught.
I became convinced that la Chiquita was a heavy sleeper.  Up to this point, I thought she didn’t know what was going on, so I decided to take the groping further.  First, I began by rubbing my crotch against her butt while I caressed her breasts, but then I decided to go for her private parts. Stroking la chiquita’s butt.  I would grab the top of her *** cheeks and gently work my way down to the thighs into her inner thighs.  Trying to reach for her vagina was what took this game to a different level.  Since I didn’t know at all about female anatomy, I remember thinking the ***** was all the way in the front of her crotch, so I thought it was impossible to reach it from the back.  There was too much risk in getting my hand caught between her legs, so I decided to do it from the front.  I remember that night so well, like if it was yesterday.  I was more excited than nervous.  I went for the usual hug, did the usual rubbing, then I put my hand right on her lower abdomen and I started to move down slowly.  Every time she moved, I would stop.  I felt her ***** hairs.  Instinctively, I almost removed my hand, but I stopped and kept working my way down.  I still remember the feeling on the tip of my fingers when they finally reached the *****, where the “V” starts.  She twitched and released a moan. I immediately stopped and moved my hand up to her lower abdomen again.  Then, I went at it again. This time I reached the tip of the “V” faster than the first time, but she twitched again with a moan and I retrieved my hand once again.  I didn’t know that she was releasing those moans because I was unknowingly pleasuring a fully awake woman.  However, I just decided to give up for the night, I thought she was twitching and moaning too much and I didn’t want to get caught, so I turned around a bit disappointed to see if I could cool down and fall asleep.
To my surprise, I felt La Chiquita turn around.  I immediately froze. I felt her get close to me, her breasts pressed against my back, her crotch pressed against my ***.  She was spooning me now.  I was freaking out, but couldn’t move.  Suddenly, with one magical stroke she went directly for my hard *****.  I jumped.  She felt it over my shorts, noticed its stiffness, and followed the shaft with her fingers slowly, pressing the fabric against it.  Then, she slid her hand inside the underwear and started playing with my *****.  She was ******* me off… just like that, like if she was trying to catch up with me for all the nights she's been letting me fondle her. It was a good thing we were sleeping on a carpet on the floor, there was no shaking mattress to give us away and my brother, who slept next to me, was pretty far from me.  I was just laying on the carpet with a 32 year old woman giving me a hand job.  Now, it was me who was releasing some moaning, her grip was soft but firm and her rhythm consistent; she definitely knew what she was doing.  When she noticed I was about to climax her stroking pace changed from fast and hard to long and slow strokes and I exploded.  My *** smeared all over with boxers.  I was mesmerized, feeling the spasms from my ******. I heard her release a smirk.  Then, she removed her hand from my defeated *****, cleaned herself with the back of my shirt.  Then, she turned around, covered herself up with her blanket and fell asleep.  A while passed before I was able to do the same.
When I woke up, “La Chiquita” had already gone to work. I had missed the morning show. I couldn’t concentrate the entire day in school thinking about the night before.  It seemed like a dream; maybe it was a dream.  After school, I went home ready to jerk off to one of her panties again.  I did.  I was horny as hell.  I was desperately waiting for her to come back from work, but when she did, I didn’t even want to look at her, I became completely shy.  Whenever I glanced, she would give me some soft, but sinister smiles.  I avoided her all night, even as we went to sleep.
Like every night, I laid down by her side.  My siblings and “La Chiquita” talked about trivial stuff for a while as I pretended to fall asleep right away giving my back to her,  I was so nervous and horny at the same time, quietly breathing hard, but I wasn’t going to do anything, I was afraid. Suddenly, in the middle of the night, I trembled to her touch.  It was her who had changed covers now, and was spooning me again.  Again, she reached for my ***** and started caressing the tip with his fingers.  The ***** got hard immediately.  I wasn’t moving, but as soon as I felt her firm grip close around my rod I was ready to explode again, but then she stopped and whispered in my ear “volteate”.  I didn’t move.  She turned me around.  Her face, her eyes were on fire.  She said “ahora es mi turno” and covered me with her blanket.  She turned around and pressed her *** hard against my ****, then, she took my arm and wrapped it tightly around her waist.  I thought for a second that that was all she wanted, to fall asleep spooning each other, but then, she lowered my hand down to her ***** and said “Esto es lo que querias?”  She started to rub herself with my fingers as she dry-****** my **** with her ***.  The experience of feeling a wet ***** for the first time was incredible. Instinctively, I started to move the fingers on my own, trying to follow her rhythms. She would give me further instruction by grabbing my hand and placing it in the right places saying “Asi… Asi.” She curled all my fingers except the middle one and inserted it inside her *****, then two fingers.  It was not longer until I felt her heavy breathing and orgasmic shakes against my body.  After, she didn’t move for a whole minute or more, and then removed my hand, said “Que rico!!” and got ready to sleep.  I remember smelling my hand, my fingers, licking the tips, curious about the taste.
Days passed.  Our relationship had become based on us ******* off each other every night and that’s it.  However, “La Chiquita” wanted more. A couple of weeks after she jerked me off for the first time, while I was finger ******* her, she whispered in my ear “Quiero que me lo metas.”  I didn’t respond.  I never did much talking during our sessions.  Suddenly, she worked her way down to my crotch under the covers and began giving me a blow job. I still can feel the first time her tongue curled around the tip of the head, getting ready swallowed my rod like a hungry snake, and how hard she yanked my balls to stop me from *******. She came back up and as usual pressed her *** against my *****, but then she bent further over, to leave her ***** exposed and ready to be penetrated.  She lifted one leg up a little bit while reaching for my ****.  Then, she tried to put my **** inside her, but I wasn’t helping.  I was clumsy, laying still. She kept moving and accommodating herself, doing all the work, ************ me by pressing it hard against her wet ***** with her hand, until I felt it penetrate, but then in an awkward move it went out again. By then, she had gotten so frustrated, she decided to mount me.  I was so nervous, I panicked “se van a dar cuenta” I told her with worry while trying to get her off me.  She was so light, I easily could have lifted her and put her aside, but she voluntarily got off, laid down, turned around and went to sleep angry.
Two days passed and she wouldn’t let me touch her anymore. “La Chiquita” would aggressively remove my hand as soon as she felt it.  I would hug her or try to spoon her, but she would just forcefully remove herself from me.  I thought our rendezvous were over, but a week later I was so horny that I wasn’t going to take no for an answer.  I waited for her to fall asleep to go for it again.  I must have been around 2am, when I decided to move fast.  I grabbed her body with both of my arms with a strong hug and pulled it against me.  Keeping her tight, I moved one hand up to work on her **** and one hand down to work on her *****.  She woke up and elbowed me, but I was stronger and just pressed her tight against my body.  I already had a good idea of how to rub her ***** the way she liked it… Hell!!  I had been already doing it for the past two months or so and that’s what I did.  She gave up in less than a minute.  By the next minute, she was rocking her *** back and forth, pushing my finger inside her wet ***** as deep as possible, thrusting her ***, dry-******* me, letting me be violently finger-**** her.  By the 3rd or 4th minute she came all over my hand.  Suddenly she said “Vamonos para el closet.”  I nodded.  I wasn’t going to make the same mistake I did a few days ago, even if that meant getting caught.  All I had in my mind what the need to have her suck my **** the way she does.

The bedroom closet occupied the entire width of a wall at the opposite side of the carpet, it was 9 ft wide by 2.5 ft deep and more than half of it was empty. “La Chiquita” got up, silently walked, slid the door open carefully, and disappeared inside the closet. I followed. There was plenty of room inside. A soon as I went in, she violently French-kissed me for the first time, while pulling my shorts down and closing the door shut. Things started to move really fast.  With one hand she threw some clothes of her on the floor to lay on, and with the other she had a good grip on my ****, ******* me, all while violently kissing me and biting my lips. I was feeling liberated, unrestricted.  I was finally licking her **** and fondling her body the way I wanted to. She laid me down, and it was finally about to happened.  She mounted me.

The session didn’t last that long. She rode me hard, tight, and mostly, fast; not up and down, as I was expecting (like in the few **** movies I've watched), but back and forth (I still remember thinking this was weird) until she came.  Then, she modified the riding position. She leaned back holding my legs with her hands.  “Que rico” she said again “te gusta ver como entra y sale de mi chocha?” she added when she saw my eyes fixed at the penetration point.  She was enjoying her moment of triumph.  She saw it in my face I was about to ***.  At the right moment, she pulled my **** out of her “chocha” and finished me with a good hand and blow job at the same time.  I came.  I was laying on the closet floor, beaten, with *** all over my chest, belly, her hand, some on her mouth and she was just seating on my thighs, looking at me with a satisfied smile; then, she passed her fingerer through my abs gathering my *** and licked them saying “Sabes rico.”  She then stood up, thanked me (I remember this) told me to wait there for a few minutes so no one would notice, I did, and left for the bathroom to clean herself up.
After that night, we became regular sexual partners.  We had sex every day and not only around 2 or 3 am, but every time we had an excuse to be at home alone.  This lasted for the next 7 or 8 months that she lived with us. It all ended when they moved out and went to live upstate (I wished she would have moved nearby), with other family members, looking for better job opportunities I guess.  I became depressed for a while again, but something fundamental had changed in me.  I felt different; I felt I was a man, with man’s needs.  I wanted to study to go to college, I wanted work part-time, I wanted to have a girlfriend (older than me of course,) and I did.  I did find a girlfriend almost 3 years older than me.  I remember how surprised she was when she realized I knew how to sex her right.  I did find a part-time job.  I decided to go to the Marines before I went to college, but I did graduate from college.

I almost forgot to mention a funny note about this experience.  La Chiquita would wake me up every morning to let me watch her change. She would improvise a striptease, and when she was done clothing herself, ironically, she would put money inside my pants that usually were folded on top of a chair. It wasn't much.   It was usually 5 or 10 dollars, but it was plenty for a 15 year old.

The next time I saw her, I was 24 years old, I heard La Chiquita got divorced and remarried again with a guy younger than her and had a baby.  I went camping to Bear Mountain with a bunch of college friends and forgot to buy enough liquor for the weekend.  What else is there to do during a camping trip?  La Chiquita lived around the area, in Peekskill, so I asked my family for her phone number to see if she could give me directions to a nearby store.  This was the perfect excuse to see her again.  She was so nice and helpful.  She came to pick us up and take us where we needed. She looked the same as I remembered her.  I didn’t I knew I had changed, a lot. Now, I was 5'-8” and after four years in the Marines, I was not the shorty and skinny kid anymore.  She chatted with my friends present, but we knew we had a thing pending, so when she brought us back to the camping area, I told my friends I needed to go with her for a bit to do a family related “thing.”  We went directly to a motel. I wanted to prove a point.  I wanted to **** her brains out.  I wanted her to feel the man I had become.
As soon as we drove off, we started kissing, like the old lover we were.  We kissed her all the way to the motel bed.  I started to undress her.  The roles had switched.  She was the quiet and nervous one now.  I managed to get her fully naked while I was still fully dressed.  I wanted her to be at my mercy.  Naked, I began to finger-**** her and grab her and lick her all over.  I removed my shirt and she just stared at my chest.  She laid on the bed.  The Marine-Corp push-ups had paid off, she was shocked.  Then, I pulled down my pants right above my knees.  I didn’t take off my boxer briefs; instead I just pulled out my ****, already hard, from the boxer’s hole.  She suddenly said “has crecido… has crecido bastante.”  I asked her “Quieres sentir que tanto he crecido?” Then, I pulled her body from her legs to the edge of the bed and got on top of her.  I allowed her to feel my **** hit her crotch while I kissed her, thrusting back and forth.  Then, as I put my chin on her mouth, I penetrated her deep and hard, in one stroke.  The first **** was intense and short.  We both came.  I was proud I made her scream.  “tantos recuerdos” I said and laid next to her.  I missed her body so much.  We chatted for a few minutes.  La Chiquita thought we were done, because when I initiated a second session she was a bit surprised, but delighted at the same time.  So, she immediately bounced on top of me and began giving me a blow job.  With the first nut out of the way, this second time I wanted to take it easier.  I played with different speeds, positions.  I wanted to show her what I had learned in the past 9 years we hadn’t seen each other.  I did.  When we were finally done and leaving the hotel, she put 50 dollars in my pocket and said thank you, for old time’s sake.  I accepted, as I always did.
La Chiquita got me so used to getting paid for sex; there have been a few times now that I've had sex with older women and they end up paying me somehow.  I’d do it for free, because I like older women.  They are my preference.
So, this is the story of how I lost my virginity and became a gigolo at the same time.  Hope you enjoyed it.

Adritar Adritar
26-30, M
2 Responses Mar 3, 2010

i'll put in parenthesis the translations when i have a chance.

I absolutely love this story. Although I didn't understand some of the Spanish or whatever, it was still and excellent story.