My Sexual Biography – True Life Experience

My name is Jay, 40 years old, single man, from south India. This is not a story. This is more or less like 27 years of my experience with women.

Right from child hood, woman’s breasts fascinated me. I wouldn’t miss a chance to see one. While growing up the only options was to steal glances at women breast feeding children. At the church, in a restaurant, parks, bus stand, where ever I could. I would always get a hard on. I could never understand my attraction though. I was always confused if it was sexual or just curiosity.

My first ever encounter with a woman was when I was a teen. We had a maid servant at home who had lived with us from the age of 10. She was 18 years old at the time this happened. We used to play together and once while we were playing with a ball and for some reason I put the ball inside my t-shirt. She jokingly said she has balls inside her blouse too. And I asked her to show it and she got shy and said no. That’s how it all started.

I got curious I spend the rest of the evening trying to convince her to show me her breast and touch it. She kept saying no. finally while she was having dinner she let me touch her breast and I remember, standing beside her and feeling her breast above her blouse and pressing them. I felt them and before leaving I felt guilty and promised her that I would never repeat it again. Life went on as usual after that and may after a few months and I don’t clearly remember how I ended up touching her breast again. All that I remember is that I touched her breast once more and from then on it became a regular habit.

Once she was cleaning my room and she was behind the door and I fondled her breast and got the courage to lift her blouse and suck her nipples. I don’t think I felt it as a sexual act at that age. I was waiting for the day I would be left alone at home with my parents gone to work. I kept stealing chances to touch her breast or suck her nipple when ever I could. Once my parents went to work leaving us at home and I got my first opportunity to lift her blouse and suck her nipple with out the fear of getting caught.

I spend a lot of time sucking her breast she though did not show much interest, always let me with reluctance. I used to sneak in to the kitchen where she sleeps every night and lift her blouse and suck her breast. She used to sleep with out her bra and I would kneel down beside her and suck her breast. Once with no one at home, we were lying down on the floor I was on my stomach and my penis was hard and was rubbing on the floor while I sucked her breast and I experienced my first orgasm. I did not realize what was going on at that time. I got up after a while and went in to the toilet and my penis was all wet. Next few days I spend in confusion wondering what is happening to me till one day I got in to the toilet and started shaking my penis and had my first ejaculation. I did not know anything about sex or reproduction at that time. I liked the experience.

One day while I was masturbating some thought about my chemistry teacher who was pregnant at that time. I remember thinking about her exposed stomach and it felt wonderful while I ejaculated. The rest of the days were spending fondling and sucking her breasted when ever I had the chance. It was always limited to that and it never went beyond that to even kissing. I was in 12th standard when my parents decided to marry her off and she stopped coming to work. Three months later started her coming to work again and I kept my distance from her the day she joined back work, she was cleaning my room and she was inside the toilet in my room. She smiled at me and went in to the toilet. I couldn’t control my urge to feel her breast and I put my hand in to the toilet through the door and touched her shoulder.

She offered no resistance and I touched her breast. After my parents left for work I caught hold of her. I was sitting on my caught and she was standing close to me. I removed her sari to one side, opened her blouse, unhooked her bra and hungrily sucked her breast. She held me close and kissed my forehead that day. I laid her down and got between her legs; lay myself on her with my penis touching her vagina above the panties and dry humped her while I sucked her breast.

She told me about having sex with her husband while we did that. Our encounters continued till one day I was fondling her breast and for the first time I pulled up her skirt and saw her naked thighs and I took out my penis to show her. I couldn’t do anything beyond it because there were people at home. That day when I got back home from college my mother told me she is pregnant and won’t be coming to work. I went off to a college far away after that and did not come home for a year. After 2 years I came back home for my vacation and she had joined back.

After my parents left for work, I caught hold of her and went straight for her breast. I sucked her breast hoping to draw milk. I couldn’t get any. She asked me to take more of her breast in to my mouth and suck harder. For the first time in my life I tasted breast milk and I have never left an opportunity to suck on her breast after that. I went back to college and came back six months later just to suck on her breast. She was trying to stop lactating and I did not let her and continued to suck her milk. She got pregnant again and she stopped coming to work after that. She joined back after delivery and I continued my breast sucking when ever I came home. It never went beyond breast sucking for all these years.

Once when I came back home from college, my mother told me that she had a miss carriage and had not been coming to work. She joined back before I left and for the first time in my life, I tried to have sex with her. I had her against the wall and I was having a passionate breast sucking session and I was trying to enter her. I remember her telling me to stop saying, she has one more appointment with the doctor and she would know if I entered her. I still tried to and I could not enter her properly.

In the whole process my lips touched hers and we kissed. It was more like an experiment or curiosity. She was always least interested. Next day I tried to enter her again and I managed to insert my penis in to her vagina and tried to have sex. I relished the moment of feeling her vagina muscles around my penis. I did not go any further of the fear of making her pregnant. Few days later I stole one of my father’s condoms and entered her vagina and tried to make love. I was still scared to come off in her vagina but she showed a slight hint of having enjoyed the moment by hugging me close to her.

Then I went back to college again and cam back after 6 months. First chance I got I shoved my penis in to her vagina her from behind despite all her struggles to stop me and kept pounding her. She kept saying no and I did not stop and pulled out from her vagina just before I ejaculated. The kissing and feeling her vagina and breast sucking continued till I went back to college again and then I came back after 6 months. She was still working and I went near her and she yelled at me and said I made her pregnant.

I left am silence and I did not know what to do or say and thought of ending my life. 2 days went by like that and I got her alone and asked her again. Then she said she was scared if I came inside her and seduced her husband to have sex with her just in case she got pregnant and she was actually pregnant. She was angry with me for making that happen and that was the reason she yelled at me. She stopped coming to work after that and I never got a chance to be with her. She would visit occasionally and I couldn’t do anything. Then I left the country and did not see her for about 5 years.

I never could manage to get in to any relation ship all these years. I was reluctant and shy and inhibited. My sex life was limited to regular masturbation. I had fear of commitments.
I came back home after my fathers demise and that is when I entered the world of online chats. I started having women friends and I always wished to meet some one with I could have sex. In between I came to know that my old maid had some health issues and she had to have her uterus removed. I was walking out of my house one day and I bumped in to her. She told me she had gone to the hospital to have her blood sugar checked. She said she needs to do fasting sugar and asked me how. I remembered that we had a sugar testing equipment at home and asked her to come the next day morning. She came after my mother left for work and I checked her blood sugar.

After doing it her finger was bleeding and I sucked her finger. She smiled and I opened the buttons of her gown and found her nipple and started sucking it. She cooperated with out much passion as usual and I led her to my bed room and entered her vagina and started making love to her. She just lay there and I asked her if it’s ok to come and she said yes, and for the first time at the age of 29 I felt how it feels to ejaculate in to a woman’s vagina. It again felt like an act, with out any passion involved. I got to have sex with her one more time after that by chance. I tried to have sex with her at home many times after that and she never came near me.

Mean while I was quite active in online chatting. I got close to a widow called Chandra from another town who was about 60 years old at that time. The first time we had a chat on yahoo she said she has webcam and we started video chat. She would slip in some naughty statement while we chat. We went on chatting and I felt guilty about having obscene conversation with her tried to stop. It did not stop and our conversation went on, and I managed to talk her in to opening her blouse and showing me her breast.

It went on for months and she would suddenly stop one day, and disappear, saying she’s feeling guilty, come back again and it continued on and off. Though she was living about 5 hrs away from my home town I never made an attempt to meet her. Our encounters were limited to video chats. She always made it like she’s being a mother offering me her breast and it never got sexual. Once I had a chance to go to her town and I called her and she asked me to come over to her apartment where she stayed alone. I went there and we got talking and I wanted to feel her breast. She showed no sign of initiating it.

She told me her shoulder hurts and I got up and went n stood behind her. While she was seated and pressed her shoulder and my hands moved down to feeling her breast. She started moaning and I knelt down in front of her kissed her exposed stomach and pressed my face on her breast and tried to open her blouse and suck her breast. She asked me if I would talk about this to anyone and I promised her I won’t.

We shifted to the couch and she put me on her lap and she asked me to open her blouse. I opened her blouse and went around and opened her bra and placed my lips on her nipple, which for about 2 years I had seen only on the computer. I sucked feverishly and she asked me to get up and shift to the bed room because we were sitting right in front of her husband’s photo. I continued my sucking and fondling lying beside her and she said I am like her baby who is suckling her breast and kissed me on my lips. I continued for a long time and it stopped eventually.

We went to the kitchen and were talking. I came back to bed and she came and sat with her back to me and was making a phone call to some one. I sat behind her and started feeling her breast from the back above her blouse. She finished her phone call and I continued to play with her breast. I opened her blouse and pressed and kneaded her nipples above the bra. I opened her bra and felt her nipple and roughly fondled her breast and she was moaning. It was a new experience for me because my maid never made any sound or shown any sign of enjoyment, what ever I did to her.

She suddenly got up and pushed me back on the bed. I could see the hunger and passion on her face and she lay down on top of me, pushing her nipple in to my mouth and I sucked both her breast. I placed her hand on my penis and asked her to feel it. I pulled out my penis and made her shake it. I asked her to suck it and she refused. I continued to fondle her breast and had half a mind to put my penis in to her vagina. I looked at her vagina and decided not to go any further. I left her house a bit later, though she asked me to come back to her place I never went back. Then we lost connection and haven’t heard from here ever since…

As I grew older my health started going down. I was diagnosed with a life threatening illness. My yearning to be with some one increased and my loneliness started killing me. I was still active on chats hoping to find some one. There was this girl called Annu whom I had met on line. We were very close friends and it continued as a very healthy friendship. Then she got married and we completely lost touch for a while till she called me one day. She sounded quite depressed and she told me about her marriage not working out. It was more or less like a confession of her love for me. I tried to fight it of the fear of losing a friend.

Finally I started giving in. I am unable to explain the exact feelings I or she had. I decided to go and meet her and I reached her house and she was alone at her house. We sat there talking and at one point I kissed her and she repelled back. She said she has issues with being touched and kissed and feels nauseous. I tried kissing her a few more time but it never got passionate.

I visited her a few more times and the last time I visited her I managed to kiss her with a lot of reluctance from her side. Once we were on the floor with me trying to kiss her and I snapped opened her bra once. She found it disgusting and asked me to put it back. In between we went out for lunch and met her husband. We came back home and started our reluctant make out session again. I managed to open her bra and lift her churidar top and suck her breast. It was very brief. I left her house a bit later and did not hear from her for while.

In between I met this lady called Anna on line. She was married with 2 children. We kept talking the whole night and we met the next day. It was the beginning of a friendship and it went on for a while. I lost touch with her in between and then we got back in touch. We started meeting often driving around and she told me one day she wants a boy friend. I jokingly said I will be her boy friend. She took that seriously and we started having naughty conversations.

I started feeling her up when ever I got the chance. I would touch her hands, feeling her hands and touch her breasts. One day while chatting I told her I am attracted to her breast. She was shocked with my boldness and twice she lifted her top and showed me her bra clad breast on webcam. Finally one day she called me home and I went there in the after noon. She fed me lunch with her own hands and then we were on the sofa. She was over me and was licking my face and kissing my eyes and biting my cheek. I caught her face and kissed her on the lips. She continued to lick and kiss and suddenly thrust her tongue in to my mouth. We kissed passionately and I tried to touch her breast. I lifted her top and sucked her breast and she pushed me back.

We continued kissing and I felt her breast above her top. I had to leave soon because; it was time for her kids to come home. I left her house and we continued to talk and she kept saying she wants to make love to me and we kept planning. Suddenly she stopped talking to me and disappeared. Later she contacted me once saying she has shifted from here and I never got to meet her. We still have our occasional chats…

Mean while Annu shifted back to my home town and we started meeting on and off. I brought her home one day when no one was around and tried making out with her and kissing her again. It was as before all in vain. Once on New Years Eve I went to her house and for the first time she let me kiss her on her lips with out pushing me away and feel her breast and asked me if I would kiss her in front of her husband. We continued to meet and it never went beyond occasional brief kissing in the car. We lost touch again and never heard from ever since.

Then life returned to normal and I went back to being lonely. My health issues peaked and I was working off site on a project away from my home town. I met Grace there. 40 years old, married with 2 children. Average looking with huge breasts and my attraction was instant. We all used to hang out together after work and we became close friends soon. I had to go for a surgery and before leaving I came back to my home town. Grace was also in the same town with some work.

One day she asked me to come over to her hotel for dinner. I went there for dinner and was about to leave and she asked me to come up to her room. I went up to her room and we were on the balcony talking and she said she loves me. She held my close to her ample chest. She kissed me on my left cheek and right cheek and before I knew she kissed me on the lips. I was shocked and I slowly walked in to the room with her and sat on the cot and I was a little nervous. She sat next to me and said it is okay and she doesn’t expect anything from me.

We started kissing and for the first time in my life I kissed with both her and me with out being reluctant. I laid her down and continued kissing and tried feeling up her big breast while I was kissing her. She looked at me for a second and pulled up her top and bra and pointed at her breast with her face and asked me to suck. It was nothing but kissing and sucking breast and making out for the next 3 hours. I would suck both her breast together and she would be moaning while I did so.

It went on for the next few days till I left. I met her again after I came back and we met again a few times and nothing happened beyond her jerking me off. She went back to her work place and we continued to have sex chats. I was multi timing between Annu and Anna and Grace. Finally Grace started forcing me to take it beyond a make out relationship. I could never bring myself to tell her that I loved her. I did not. We started to have fights and would stop talking to each other. She would come to my home town and we would meet and make out.

Finally one day she asked me to make love to her. I did try making love. I never bothered to get any protection and I did not want to do it out of the fear of making her pregnant. We lost touch again. We got back in touch again after a break. She had some health issues and she had her uterus removed. She told me she wants to make love to me after she recovers. She flew down to my home town, we checked in to a hotel near the airport and we didn’t wait to jump in to bed.

I spend hours sucking her breast and kissing. She asked me to make love to her and for the first time in my life I had some passionate sex. We made love 5 times in 8 hours. We would have sex and then I would be on her lap and I would start nibbling on her breast and suck them both together. We both would get horny have sex. I tasted a woman’s vagina for the first time. I had only seen and heard about it. I did not find it very exciting. She tried to suck me off many times and I could not come in her mouth. We had a break again.

My health issues took a serious turn and it became terminal. I had another online friend called Sreeja and I became friends with her friend also. Her name is Gayathri. Sreeja was a rude and arrogant girl. Gayathri was married with a kid and she was very soft heart ed and warm person and her husband was living abroad. I told Sreeja about the illness and she asked me to go meet Gayathri at her house. I was in a state of depression and I went and met her. She was very motherly with me and at one point she let me lie down on her lap and talk to her. I was on her lap and talking to her and she pulled me close to her breast. I lay their feeling the warmth of her bosom and she kissed my forehead.

I left her house and went back again another day. The third time I went there I was in a state of severe depression. I was on her lap and she was holding me close to her breast. She was kissing me on my fore head and at one point she had her lips almost touching mine. I moved up and kissed her on her lips. And she kissed me back. I put my tongue out and we went in to deep kissing frenzy. I stopped and she kept me held on to her breast. I could feel her nipple pressing through her churidar top and I was feeling it with my lips. She asked me what I am doing.

I told her I felt like suckling your breast. She asked me if it’s sexual. I told her I don’t know. She was quite for some time and then she slipped her nipple out of her bra and let me suck it above her churidar. She did not expose it. I sucked as much as I could. May be it was the state I was in I broke out crying. She tried to stop me.

Then she pulled out her nipple and pushed it in to my mouth and I sucked on it. She placed my hand inside her churidar and made me feel her other breast while I sucked on one like a baby. We both sat up after that and she was feeling guilty. I left soon after and later she called me and said to consider it only as her being motherly to me.

I did not meet her for a while. Her birthday came up and I called to wish her and she asked me to go meet her at her house. I went there and brought her a small gift and I kissed her. She kissed me on my lips and it broke out in to a passionate kiss. She was wearing a sari and she sat back on to the sofa and I lay down on her lap.

She moved back, shifted her sari and started unbuttoning her blouse and said. Last time I was in a trance. This time I know what I am doing. I want u to suck on my breast and pushed down her bra exposing both her breasts to me. She pushed her nipple in to my eager mouth and placed my other hand on her free breast and made me fondle it while I sucked hard. I looked up while I was sucking her and all I could see was passion. I sucked like a baby carefully hiding my hard dick from her.

Then she lay down flat and I sucked her breasts in alternation and kissed her pushing my tongue in to her mouth. It continued till I slept off sucking her breast. I woke up after a long time and sucked her breast for a while and left. I went back after 2 weeks. She was confused and did not want me to come. Sreeja smelt something is wrong and asked me to stay clear from Gayathri. Gayathri called me and asked me to come and told me not to let Sreeja find out. We did not have much of a conversation. It was pretty much deep tongue kissing and me sucking her breast all the time.

I sat on the edge of the sofa and lifted her churidar top and pushed down her bra and held her close to me. Pushed my hard on in to her crotch and sucked her breast one my one. I would bite it and pull it and suck it hard and she was in a state of bliss.

Then we met for the last time. She was due to leave my town and go away for good. It started as the usual kissing and breast sucking and fondling. Then she lay down on my lap and she felt my hard dick. She traced it with her mouth over my jeans and touched it and felt it in silence. She never attempted to take it out. Then I got up to leave. Her hand was constantly on my hard dick and we kissed till I left. Before I left she told me that this relationship has to die with us and none should know…I haven’t heard from her after that.

I reconnected with grace again and we had sex one more time. We spend the night together and we realized our passion dying with every passing encounter. There was not much of a conversation and it was just breast sucking and sex and oral sex. We lost touch again as usual.

I was continuing my search. I had purchased a small apartment and had an issue with finding some one to clean it. I decided to ask my old maid if she could help. After a bit of a forcing she agreed to come. We reached the apartment and I did not waste a second to hold her and fondle her breast. She resisted first. But I managed to take her to the bed room and open her blouse and suck those boobs. She had become old and her boobs were saggy. But I couldn’t stop. I sucked her boobs and spread her legs and entered her. I made love to her feverishly. She started cleaning the house and I waited till she finished.

After she finished she came to my room to tell me it’s done and I pulled her in to bed and made love to her again. I dropped her back home. 2 weeks later she came again and just like last time I made love to her again. She refused to come after that.

A year later again I convinced her to come and clean the place. She came and I as usual straight away went on to fondle her. I spend a long time kissing her and sucking her breast and finally entered her. While making love she asked me why I haven’t married and I told her about my health issues. She became sad and she held me close to her breast with love for the first time in 27 years. She kissed me on my lips and held me.

I stopped making love to her. She let me suck her breast and put me to sleep and I slipped off in to a blissful sleep. She woke me up later and lay down next to me. I decided to show her some love and I started touching her vagina. I fingered her till she had an orgasm. She confessed she’s having and orgasm after years. We kissed and we made love and she let go her inhibitions and we both reached our climax together. She refused to come to clean the place after that.

Then came Facebook. I’ve been on Facebook for a long time and one lady called Bindi added me. A 41 year old divorcee. I did not know who she was and she took interest in a certain posts I was doing on Facebook and decided to add me. We never spoke for a long time. In between I went in to another bout of depression and started posting hate messages on Facebook and she messaged me. We got talking and about 3 months later on my way to another town I met her briefly.

She invited me home and I went there for a brief stint and continued my journey. On my way back I stopped at her place again and stayed over. We talked the whole day and whole night and it was the beginning of a beautiful friendship. We went on being friends till I went there the third time. We were lying next to each other on the floor talking and some unfortunate incident which happened recently came up. I couldn’t stop crying and she held me close to her. I stopped crying eventually and she kissed me on my forehead and put me to sleep…I left the next day

I did not think of it as anything different till she sends me a message saying she miss being in my arms one day. I did not reply to it and thought I will let it slide. Then she called me over to her place again. I went there on a weekend and we were as usual talking away. I was leaning on the sofa and she was sitting opposite me and suddenly she hugged me and kissed me. She said she always wanted to right from the first time we met. It went on to an entire night of kissing. I felt up her breast while I was kissing her and she pulled down her bra and offered me her breast.

We went on the whole night kissing and fondling and hugging. She did not let me touch her vagina even once. Said Ill have to wait till the next time and asked me to bring condoms the next time. She also told me this doesn’t mean that she expects me to call her ten times a day or say I love her. She kept touching my penis and stripped me .After 2 days of making out I left her house ever more confused about my feelings for her.

She started acting weird after I came back home. She started blaming me for everything that happened and said she was just an experiment for me. She calmed down later and said we should stay friends. She asked me to visit her again. I went there and held on with out touching each other for a while. Then at some point we ended up kissing and again went back to the usual breast sucking, kissing and make out session. She took off her clothes and took mine off too.

We continued kissing and she placed my hands on her vagina. I started fingering her and she started moaning. Her vagina was too tight for even my finger because she had not had sex in a long time. She pushed my head towards her vagina and asked me to lick her vagina.

I spend a long time licking her and she came a few times. Finally I entered her and started making love to her. I couldn’t penetrate her properly and with great difficulty I managed to enter her vagina and started making love. She was moaning and kissing and biting me and she came twice before I could finish and went dry. I had to pull out. It went on like that for the next two days. I kept trying to make love to her and she would have multiple orgasms and I will have to stop. I completely lost interest in making love towards the end of it and I returned home after 2 days.

After another round of blame game being played, she asked me to come over for one last time. I went there and an hour later we were in bed together with me pounding away. I finally managed to insert my penis in to her properly. I came after she came twice we kept making love for the rest of the day and night and I could never come after that.

Next day we were lying naked in bed and I was rubbing my penis on the crack of her ass trying to penetrate her ass. I got really hard and with one strong push my penis penetrated her vagina all the way in. I quickly put on a condom and started pounding her from the back. She kept having orgasm after orgasm and I could feel my own orgasm building up and finally I came and collapsed on her. We kept having sex doggie style after that and we made love till we both collapsed and went to sleep. Next day morning I made love to her doggie style 2 more times and left. Everything was going on well after I came back home.

A week later out of the blue she said she is leaving and going away. I haven’t heard from her ever since…

This has been my life’s journey of sex. I do agree that it hasn’t been perfect. I wrote it down because I wanted to look back on it in one go and realize what my yearning in life is. I don’t really understand if I was right or wrong. I did have my moments. I am not sure to cherish them or forget them, because; there has always been a stain of confusion or fear in every single one of them.

I am almost in the last stages of my illness and I still live in hope. That I would find some one who would for once; hold me with passion and love and affection, with out inhibitions or motives before I die.

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