Falling to the dark side

[Taz7776]

I'm no story teller. In fact I've had girls who would talk to me just so that they can be put to sleep. But I'm at a stage where there is internal turmoil. It's been a long journey from me being a loyal man to one that has fallen hard and just screwing around. One part of me enjoys it while the other is greatly tormented. Let this be a journal. I will just update whenever I find time and in the mood. There may be descriptives of my encounters. All names will be changed for obvious reasons. I welcome all comments and criticisms as I trot along with my notes.

I come from a family where I think all the guys in the family had affairs, my dad included. My dad rotates through various but then there was one where he was more involved. I got to know much later that even then he had other younger girlfriends during his time with the mistress. It was an open secret and my mom sort of accepted that as well. However things got over board and my mum decided enough was enough and called it quits. Now my dad does take care of the family financially but I guess he just have to satisfy his sexual needs outside. All these made me hated my dad and told myself I will never be like him or any other uncles in my family.

I am blessed with my dad's good looks I guess and it was never too difficult for me to make a good impression with the ladies. But that only gets me so far. Being a goodie two shoes I guess is just too boring for the ladies and I always ended up being dumped. But that never stopped me from wanting to be the good loyal guy. I only lost my viriginty when I became an adult and it was because my girlfriend then asked if I don't love her and that's why did not want to have sex with her. Hahaha and I thought that was a line by guys to pressure girlsminto having sex. Guess that works both ways. My firs time was car sex. Back in the days, I'm sure more senior guys would have recalled the various carparks without lights.

The girlfriend whom I lost my virginity to, let's call her E. E had a decent figure and was pretty. When can easily get attention in clubs. Her breast were a nice b cup but felt very good. Little tiny earaser nips. She enjoys sex and we would do it everyday, sometimes few times a day. We were young then and threw caution to the wind. Unprotected sex. Sometimes I will cum in her as she enjoys that too but most times I just shoot outside. Thinking back our sex was quite normal. Only once we did a animal role play. I recalled once when I got so excited that I came within minutes of thrusting. I was embarrassed and did not withdraw. She pushed me away and I watched my cum dripping out of her pussy. She just quickly wear back her underwear and scolded me for cumming in her as it was a danger period.

[Taz7776]

E was sensual but we were both inexperienced. So sex was never overboard. We do have other simple sexual moments too. When in the streets shopping, she would pull my arm around her just so that I can grope her. We enjoyed the thrill. When in the movies, she would do the same, pulling her shirt apart so i can thoroughly enjoy her soft breast while being distracted from the plot of the movie that we were watching. All ended when I went overseas for study. Guess she just needed another dick to fill her up during my absence. Those were the days before good fast internet and overseas call are just too expensive. She did visit me once overseas just to let me fuck her everyday during my break but broke up with me soon after her return.

There had been near sex encounters when I was overseas but I told myself that I don't do one night stands and will only do it with girls that I plan to marry. So there wasn't any action thereafter.

Got to know C when I got back to Singapore. She was a very experienced girl with lots of prior partners. Somehow that did not bother me. C was not that pretty but had a smoking figure. Nice C cuppers that grew to Ds later on. Nice ass that were just so nice to grab. I remembered a time when she was wearing a dress and I just could control myself and kept touching her butt when we were travelling up an escalator. C made me enjoyed blowjob but I hardly let anyone blow me since as few come close to her skills, even the pros. C will always wear nice underwear, just the way I like them. Now that I think back, I am not sure if I like those type of lingerie from then or she conditioned me to like those style. C had wild friends, suggesting threesome and even with her lesbian friends. It's a shame that I'm not that kind of guy then. Thinking back now, I should have just upped all of them then and cum in their pussies.

C was fun to be with. She showed me to the good taste of life, bringing me to nice restaurants and all. Sex never needed foreplay for her which was fine by me then. Watching those tits bounce were a sight. Thinking back, she had one of the nicest feeling tits. I will be enjoying the feel of her tits now if I allowed again. We were together for a long time, but things got boring for her. I'm all about saving for tomorrow while C was living the moment to the max. She finally broke up with me when someone entered her life giving her more fun. C did not get married and from what I know. still single. But good thing she dun do married guys like I am now. If not I'm sure I will be fucking her when possible.

I had always thought that C will be the one to go the distance with me. She has her flaws but that never bothered me. She takes care of me and my life like a good partner and I thought sex with her was always amazing then. Her leaving me somehow broke me. I'm leaving full details out for this in case the details will somehow reveal our identities. Let's just say that things happened and her leaving me just broke me.

[Banaber]

a dark knight rises. [cue theme music~]

[enigma88]

Thanks for the story so far. Great start. Please continue.

[Taz7776]

C and I were together for quite a number of years. That was a time before camera phones. As both of us were sharing rooms with siblings our sexual escapades all happened in hotels or cars. Was never a great fan of hotel sex and we ended up doing it often in car, either my dad's or her dad's car. We would explore different isolated or dark spots in Singapore just to make out or go at it.

While C had wild friends and she had lots of boyfriends and sexual experiences before, she was rather conservative when it comes to dressing. Always simple single colour t-shirt or shirt with jeans or pants. Very rarely dresses or skirts. However there was one time when we were clubbing, she wore a tight outfit that was quite thin. The outfit just highlighted her ample breasts and nice ass. I will not say she is a head turner type but she sure got lots of attention that night. She was wearing white bra and underwear that night and they showed through her thin outfit and everything just clicks. Her every dance moves swayed or bounced her breast. Her ass just looked the more delicious that night with her outfit snuggly hugging them and her white underwear online clearly visible through her outfit. The club was crowded and I'm sure lots of guys were looking her way ever so often but I could not care less. The sight of her outfit, her moves and her breast and ass just drove me nuts. I danced closed to her body. Rubbing my erect dick against her curvy ass and running my hands up and down the side of her body, purposely glancing through her breasts ever so often and giving them a nice squeeze whenever I needed to. She was obviously aroused too. Turned around and threw her arms around my neck while I continued to gyrate our privates. We locked tounges and my hand just automatically went for her breast, giving it a good hard squeeze. The feeling just heavenly. Till date I don't think I've met more then a handful whose breast feeling can match hers. I slipped my hand further south and went up her short dress, moving her panties aside and quickly slipped my finger into her virgina. I was crazy, she was high from all that and was obviously wet too. She pulled my hand out quickly, but gave me the naughty looked and licked my wet fingers, then gave me a slapped on my arms, as if to say I should not done that.

We still stayed on and enjoyed the night. But end of the night we went to one of our usual spot and parked. We normally have protected sex, but that night, all rules were broken. She started sucking me while we were driving there. I groped here every now and then while keeping concentration on the road. Luckily it was late already and traffic was light. As mentioned, she has the best blowjob skills. Once we parked, I just threw her to her side of the car, climbined over, pulled down her panties and just inserted. A whole night of teasing just was too much. I did not last too long. She knew I was cumming, pushed me up and turned me around, went down on me and let me blow my load into her mouth. She looked up smiled and swallowed every bit of it.

[Revolutionx]

Originally Posted by Taz7776

C and I were together for quite a number of years. That was a time before camera phones. As both of us were sharing rooms with siblings our sexual escapades all happened in hotels or cars. Was never a great fan of hotel sex and we ended up doing it often in car, either my dad's or her dad's car. We would explore different isolated or dark spots in Singapore just to make out or go at it.

While C had wild friends and she had lots of boyfriends and sexual experiences before, she was rather conservative when it comes to dressing. Always simple single colour t-shirt or shirt with jeans or pants. Very rarely dresses or skirts. However there was one time when we were clubbing, she wore a tight outfit that was quite thin. The outfit just highlighted her ample breasts and nice ass. I will not say she is a head turner type but she sure got lots of attention that night. She was wearing white bra and underwear that night and they showed through her thin outfit and everything just clicks. Her every dance moves swayed or bounced her breast. Her ass just looked the more delicious that night with her outfit snuggly hugging them and her white underwear online clearly visible through her outfit. The club was crowded and I'm sure lots of guys were looking her way ever so often but I could not care less. The sight of her outfit, her moves and her breast and ass just drove me nuts. I danced closed to her body. Rubbing my erect dick against her curvy ass and running my hands up and down the side of her body, purposely glancing through her breasts ever so often and giving them a nice squeeze whenever I needed to. She was obviously aroused too. Turned around and threw her arms around my neck while I continued to gyrate our privates. We locked tounges and my hand just automatically went for her breast, giving it a good hard squeeze. The feeling just heavenly. Till date I don't think I've met more then a handful whose breast feeling can match hers. I slipped my hand further south and went up her short dress, moving her panties aside and quickly slipped my finger into her virgina. I was crazy, she was high from all that and was obviously wet too. She pulled my hand out quickly, but gave me the naughty looked and licked my wet fingers, then gave me a slapped on my arms, as if to say I should not done that.

We still stayed on and enjoyed the night. But end of the night we went to one of our usual spot and parked. We normally have protected sex, but that night, all rules were broken. She started sucking me while we were driving there. I groped here every now and then while keeping concentration on the road. Luckily it was late already and traffic was light. As mentioned, she has the best blowjob skills. Once we parked, I just threw her to her side of the car, climbined over, pulled down her panties and just inserted. A whole night of teasing just was too much. I did not last too long. She knew I was cumming, pushed me up and turned me around, went down on me and let me blow my load into her mouth. She looked up smiled and swallowed every bit of it.

Wow!!! Thanks for sharing.

[Taz7776]

C has a younger sister. She is quite opposite. Sometimes wonder if they came from the same genes. Let's call her sister L. L was tall, slender and very pretty. While C does have a smoking figure to me, it was on the meatier side but she was no way fat nor plump. L is your typical model figure. Part time model too. But her boobs were much smaller compared to C. Still a nice b I guess. I was a good loyal guy then. Did not venture for a grope or peek. One time I was in Cs room but C was out in living room. L came in. She was always friendly with me. She has a boyfriend so I never put much thought to it. We were talking and I can't remember what we were talking. But out of the blue she started talking about dick sizes and asked if I have a big dick. I did not answer and she asked that why don't I just take out and show her. For those expecting hot stuff after, unfortunately no. Remember I was still a good guy then. Another time L saw me coming into the room, she just took off her shorts and bared her undies to me. Excuse was that she is changing to another pair. I just looked elsewhere and did not make anything of it. When I shared that with my friends they all thought there was something wrong with L. Anyway nothing happened between us.

[Taz7776]

I got a place to stay out alone some time later. Still close enough so I can visit my mum easily but at least now I have all the freedom. C moved in with me. Somehow things started to cool down. Sex became infrequent. I had to resort to porn to relieve myself. C would be engrossed with online games and chatting with ppl online. I was very liberal and believed in having personal space and let it be. Things got from bad to worse and she would hang out with those online friends and sometimes not even come back to sleep. She obviously did not go back to her parents place as she would return in the same clothes the next day. While we always had our differences we seldom argued. But things turned bad with her late or next day returns. One day she told me what she did in the outing. I snapped and we had a big fight. She went back to her parents place. She returned a few days later and we both acted as though nothing happened. I was still angry though. That night, sleeping beside me, she moved closer to me, my arms touching her boobs. Those feelings were just too good and it had been too long since the last sex for me. I gave in and had sex with her. I guess it was an apology sex for her and she took it that I accepted her apology by having sex with her.

The situation did not get any better after that. C would continue with her ways. I would make a fuss about it and she would tell me to have my own personal life as well and not having to always spend time together. If I wanted sex, she would say if that is all I think about with her. Thinking back I really did not understand why I put up with all those behaviour. I guess I was trying to be the nice guy while dark emotions continued to build up in me.

I was working in a company that had quite a number of young female graduates then. S was one of them and she was reporting to me. S is presentable though not the very chio type. Good height, slim, but not much of breast or ass. But she loves wearing low cuts and push ups to accentuate her cleavage. She was nice to me but we were always very professional in our dealings. It was also during that period where C had to go overseas often. Sex was almost non existent between us, reducing to a twice monthly event. One weekend C came back from her work overseas. Instead of spending time with me, she decided to head out with her friends. I made a fuss and she told me to be a man. She went out anyway. Since she ask me to be a man I thought I would show her. I gave S a call to see if she was free.

[Taz7776]

Not to make excuses for myself. I think we are all responsible for our actions and we can't blame others for the things we do. But staying out on my own and only with C, the way our relationship degraded, how I was watching too much jav, probably had something to do with the way I am now. Having perverted fetishes, screwing around. Anyway, just have to document down the journey.

S answered my call. I asked if she was free but she is out already. I told her it's ok then and hung up. I was regretting the call, thinking what I wanted to happen. So what if she was free, what would I be doing. Anyway moments later S called back. She asked if I was ok. Something so simple and yet so needed at that time. I asked what made her think I was not ok, she just replied that she could feel it. She told me that she has moved her stuff a bit and she can meet me out if I wanted to. I don't know what I was gonna say to her if I meet her or what we should be doing. But I told her to meet up anyway.

We met up in a mall in town at night. Somehow she just took charged. She never asked me why or what I wanted to do. She just suggested going to a movie. I said ok and we just went to the ticketing booth. She clung on to me like a loving girlfriend and scanned through the movies showing, picked one and suggested that we should get those gold class tickets. I just obliged. She picked a restaurant and we went for dinner as the movie is later in the night. During dinner she was talking about her day, sometimes sharing things about work, but never really asked why I asked her out. I interrupted her in her talk and asked:"you know I have a girlfriend and we are cohabitting right?". S answered yes and that it's ok. She knew something must have happened but I probably did not want to talk about it so she just wants to be with me and take my mind off. She is not asking for anything and I do not need to worry.

We then hang around after dinner while waiting for the movie. Doing stuff almost like a dating couple. Sometimes she would cling on to my arm and rest her head on my shoulder. It was a nice feeling to have that attention. While she was in her usual outfit, revealing a fair amount of pushed up cleaverage, she was always careful not to have her boobs rubbed on me, even when she was clinging onto me. How she does that I will never know. Skill I guess.

[Freakz]

Nothing progress for S?

[Taz7776]

I was enjoying the night with S. It did take my mind off whatever was happening between C and me. While we were only dating, my thinking was like we were married. I should have just broken up with her but I held on and wanted to get things back on track. I thought that's what a stand up guy should do.

It was my first time in gold class theater. While C and I had watched countless movies in the theaters, we always got the normal seats. By the time we were staying together, I had gotten a home movie theater system and thus we hardly go to the theaters. S seemed excited just to be at the movies with me, or she was just trying to take my mind off and just enjoy. We watched the movie normally, just with S occasionally leaning over.

It was pretty late after the movie. I thanked her for keeping me company and wanted to send her home. However she suggested that we hang out a bit more and enjoy Sinagpores night scene. So we drove from location to location chatting about anything under the moon. S suggested to go to a spot where we can have a good view of Singapore's night view and so I drove to one of those spot. It's late and dark with only a few cars there. S lowered her seat and suggested we just chat in the car. At that point I did what all loyal guy would. I told her that I still very much in love with C and I don't want to give her the wrong impression. S looked at me then clinged on to my arm and pulled me close. This time resting my arm between her fully exposed cleavage.

S: It's ok. I know. I'm not asking for you to breakup. I just want you to not feel bad about your life. I'm happy to be your backup. Even if you were to be married, I am willing to be your woman in the shadows.

S confession, or whatever that was, shocked me. I did not know what to say but just lay quiet. S patted me like a kid, giving me gentle kisses on the cheek every now and then and just assuring me that it's ok. The sight of her cleavge, the feeling of the push up bra pressed against my arms and the kisses were just too much for me. I am after all a hot blooded male. Physical reaction took place and I was having a hard-on.

I am not sure what it was. Guilt, physical or physiological reasons, I felt my stomach aching. I told S that I'm feeling a bad stomach ache and perhaps I should send her home. S obliged.

The journey to her place was a short one. The stomachache was getting pretty bad by that point and I felt like I really needed to use the toilet. I asked if I could go her place to use the toilet to which she said yes. What I did not mention is that S is a foreigner and she was renting. But she told me that she rented the master room and this I could use the toilet in her room without disturbing her landlord.

It was a good thing I did not control till I was home. The ache was just too much. After I got out of the toilet, S passed me a glass of warm water. Simple gestures of care and concern. Again that felt really good. S told me to lie down in her bed to rest a bit. I told her it's ok and I was feeling much better but she insisted. She said it was ok and I should rest a bit more before heading home. She told me she would go washed and first and naughtily told me not to try to peep.

[Taz7776]

S came out of shower in a tight white spaghetti strap top and a tiny shorts. She was still wearing her push up bra. It was quite a sight. Her slim figure, still curvy even with the ass department lacking. The boobs department is strongly accentuated by the push ups. It was hard on downtown again. S came and lay beside me in bed. Turned around and hugged me. Her hand slowly caressing my arm, then my body and she started to roam further south.

[Taz7776]

I was definitely stimulated, high. She was wearing a nice fragrance as well or it was from the scent of her soap. I did not know how to react. Multiple thoughts were running through my head. Morals, principles, being a loyal guy Vs the feeling of the care and concern, the attention, and the physical pleasure. Before I knew it S had unzipped my pants and put my erected dick in her mouth.

The easier explaination would have been my little head doing the thinking. But it was more complicated. Whatever was happening between C and me had a great part at play too. The moment S was sucking me, the temple of my moral shooked. The anguish that had been building in me from what C had been doing sped up with every movement of S. The walls of my morals finally cracked.

S was trying her best to pleasure me. But her bbbj skills just cannot compare with that of C. I pulled S up, threw her to her side of bed and pinned her arms down. The lights were off in the room, but through the street lights that were peaking through, I can still see her heaving, her eyes yearning. I released her arms and pulled down her straps, revealing her sexy bra that is tightly hugging her breasts. We locked lips and our tougnes fought ferociously. It was for not more than a few seconds and I pulled up, pinning her arms down again.

Perhaps it was the influence of porn, perhaps I was projecting my anger toward C onto S. I was rough with S. I looked intensely into S. I then ripped her bra apart and pulled down her shorts, keeping her sporty underwear that she was wearing on. S had small boobs. But it was still shapely and perky despite her being pinned down. I went in for a hard grope then hurried my face into them. Licked her nipples and sucked them hard. Despite the small size, her breast still felt great. Not great like C's breasts but definitely up there. While Ive had only 2 sexual partners till then, I've had a number of girlfriends before that and had felt some of their boobs. S's breasts' feeling was definitely up there amongst the top few, even when compared to the numerous breasts that I have groped since then.

I was really rough with S, almost like trying to rape her. But S seemed to be letting out soft moans of both pleasure and pain. She was not complaining but held me tighter.i tried to rip apart her panties but turns out not as easy as the porn movies. Giving up on the ripping, I just snapped away her panties and inserted 2 fingers into her. She was all wet already which facilitated the entry. I was thrusting my fingers hard into her, with each thrust I can see S trying to hold in her cries of pleasure more. She had to. It was late and I'm sure she would not want to wake up her landlord.

I parted her legs and was about to enter her when she stopped me.

S:"do you have a condom? We can only do it if you have one"

I was thinking why would I ever have a condom with me? Its not like I planned this or that I'm the type that fucks around outside.

Me: I can't take it anymore.

And with that I thrusted my fully erected penis into her. She was tight. Really tight. Even tighter than E. I don't know how much experience S had before. Her vigina just felt amazing. Wet, slippery and her inner walls caressing and massaging my penis with every thrust. S was obviously shocked. You can almost see her wanting to resist but in too much enjoyment at the same time. Almost a perfect jav actress in one of those scenes.

S: don't...cum...in...side

It was like she was timing her speech with my every thrust. Those words were like a magic switch and I felt a strong urge to come. I pulled out quickly and my sperm just sprayed. Literally sprayed. My cum covered large area of her body, hit her face, one sprayed even to her eye. I tried to control the spray to within he rbody so as not to dirty her sheets. I had never cum this way nor had I cum this way since. It was really quite a sight.

[Nitrolicious]

More please! Camping here.

[funfox]

More please. Great posts 👍🏼