Category Archives: Mature

Mom’s best friend…

This is the true story of how I lost my virginity.

I was 13 and my Mom’s best friend Terri had recently walked out on her husband after finding out he was cheating on her. Terri at the time was 46 years old and very attractive (to me at least) for her age, red hair with some gray, about 5’6” tall, she was a large lady but not nasty large I guess a small BBW would be a good description of her. She had a nice round booty and big tits DD or DDD depending on which one of her bras I checked out. Terri came to stay with us for about a month while her husband moved out of their house and she got her stuff together. While she was staying with us she walked in on me in the bathroom as I was getting out of the shower, she only saw me for a minute but she saw everything.

I was nothing much to talk about, average kid, a little short for my age but in the shower at school I was always bigger than the other kids. Some of them would tease me about it but it never bothered me much as I knew they were just jealous. It was about a month after Terri moved back home that she called my mom and asked if she could “borrow” me for a day as she had some chores she needed a “man” to help her with. My mom volunteered my services and the following Saturday she dropped me off at Terri’s at around 8am. Terri was turning the basement into an office and needed help moving stuff in the basement and carrying stuff up to the attic. It was July and it was hot, Terri didn’t have AC anywhere but in her bedroom so it was hot and stuffy in the house. The basement was cooler so working down there wasn’t bad but once we started carrying things up to the attic we got sweaty.

Before we started moving stuff upstairs we took a break for some cold drinks. Terri had always been a favorite of mine, I always thought she was hot and when she hugged me I would get lost in those huge titties. We talked as we rested and she started asking if I had a girlfriend. I said no, and she said that was a pitty from what she had seen. I knew exactly what she was talking about because she had become a masturbatory favorite of mine where instead of walking out of the bathroom that day she closed the door behind her and we did everything my perverted little mind could think of. I blushed and she told me she didn’t mean to embarrass me, that I certainly had nothing to be ashamed of and that most men would give their right arm for what I had. I just kind of stammered out something unintelligible and seeing my discomfort she suggested we get back to work. She gave me a big hug which got my already growing cock rock hard and I know she felt it pushing into her thigh.

The attic was basically a hole in the ceiling on the second floor, it didn’t have one of those drop down ladders so we had to get a regular ladder from the garage to get up there. We fell into a ritual where we would pile stuff up in the hall then Terri would hold the ladder steady as I carried things up and arranged them in the attic. I was wearing a pair of loose shorts and I had gotten into the habit of not wearing underwear because all my mother bought me were tightie whities and they were mostly uncomfortable especially when I would get excited. I was up at the top of the ladder moving some boxes away from the hole so I could climb up when I felt Terri’s hand on my thigh just above my knee. I had been semi-hard ever since our discussion and hug and when I felt her hand touch me I went full on hard. I looked down and she was looking up but not at me but at the incredibly obvious hard on I was sporting in my pants. Her hand slid up my thigh into the leg of my shorts and I felt her begin to rub my balls. My knees got weak and I almost fell off the ladder, she looked right into my eyes and asked if Iiked that. I nodded yes and felt her hand wrap around my cock and begin to stroke me. She asked if anyone had ever done this to me before and I shook my head no. My mouth was so dry I couldn’t talk. She then told me to relax and enjoy. She took her hand out of my shorts grabbed them with both hands and pulled them down. My cock sprang out hitting my stomach. She grabbed it again and standing on her toes she slid her mouth down over it. I had jerked off many times but nothing had ever felt as good as this and I came almost immediately. I tried to warn her but she either didn’t hear me or care because she took my load in her mouth and swallowed every drop. She kept sucking until it became uncomfortable then as she was rubbing the head on her lips she looked up at me and asked if I liked it. I couldn’t tell her how much I liked it quickly enough and sounded mostly like a babbling idiot. She said she enjoyed it as much as I did but it had to be our secret and we could do it more if I didn’t tell anyone. I readily agreed and she said it was time for my first lesson.

She took my hand and led me into the bathroom where she stripped and we got in the shower as she had me wash her she explained the different parts of her body paying special attention to her pussy and clit. Once I had washed her she started washing me. Of course I was rock hard again. She said that she had forgotten how good a young man was got on her knees and sucked me off again. Thankfully this time took a little longer and once again she swallowed my load. We dried off and she led me to her bedroom, she lay down on her back and had me get between her legs. Then she gave me the first of many lessons on pussy eating. She had me start by kissing and licking her thighs slowly making my way up to her pussy, she had me run my tongue over her lips nibbling on them and pulling them with my lips, sliding my tongue back and forth between them and pushing it inside her. All the time she had her hand on the back of my head guiding me and telling me what to do. After sliding my tongue in and out of her a few times she guided my head up to her clit where she had me make little circles around it with the tip of my tongue then flick it back and forth across it. She started to become very animated moving her hips up into my face and holding my head tighter against her pussy. Her clit was big and all I could think about as it was rock hard against my tongue was that it was like she had a little cock. So without her direction I wrapped my lips around it like she did to me and started sucking it in and out of my mouth. She started to shake all over and cried out as she mashed my head into her pussy. She started telling me to not stop as she continued to cum all over my face. She didn’t squirt but she got really really juicy. She grabbed me with both hands and pulled me up on top of her thanking me as I got my first real kiss. Her lips were soft and gentle and she told me to slow down, loosen up my lips to make them soft and we kissed for a bit as she ran her hands over my back and butt. I was grinding my hard cock into her belly. Next lesson she told me. Rolling over so I was on my back and she was straddling my waist she asked if I was a virgin. I said yes and she said not for long. She reached behind her and started to stroke my cock and then slid her bottom back grinding it on my cock. I felt her rotate her hips back as she sat up and the head of my cock fell into the hottest wettest most amazing feeling I had ever experienced. Then she started to slide back and down and I lost my virginity as her tight wet pussy slid down onto my cock until I was balls deep inside her. She moaned as I slid into her and I knew I wasn’t going to last very long like this. She didn’t move up and down but started to just rotate her hips forward and back then in little circles. Her big tits just swaying above me as she did. This was the most amazing thing I had ever felt and I told her I was going to cum. When she heard that she started to ride me hard and fast and we ended up cumming together. She collapsed down on top of me and we kissed for a long time with my cock inside her and her slowly grinding her pussy on it. I grew hard inside her again and she sat up and started to ride me moving up and down with long slow strokes the length of my cock. Her tits started bouncing and swaying and I was mesmerized. She leaned down lifting one of her tits to my face telling me to suck it. I gladly took that fat nipple into my mouth as she started riding my harder and faster. She told me to bite her nipple gently and I did and she started cumming on my cock. As she collapsed on top of me I was fucking up into her and she rolled me over on top of her and told me to fuck her. Instinct took over and I started to bang the shit out of her pussy until we both started cumming again. We lay there side by side after making out and talking when the phone rang. It was my mom asking if Terri wanted her to come pick me up. Terri told Mom that we didn’t get nearly as much done as she had hoped for, that we hadn’t eaten yet and if she didn’t mind she would like to keep me for the night so we could get an early start in the morning. Mom agreed and I started getting hard again thinking about spending the night with Terri. Terri noticed my reaction and dove down onto my cock sucking it like a woman possessed. She threw her leg up over my head straddling my face and pushed her pussy onto my mouth. I started eating her and I could taste my cum inside her. I wasn’t grossed out because I regularly lick my cum off my hands after jerking off. We came together and ended up falling asleep in each other’s arms.

I woke up to the most amazing feeling and it took me a few seconds to realize where I was and what had happened but it all came together when I felt Terri sucking my rock hard cock. Best way I had ever been woken up. She swallowed my load again and crawled up on top of me kissing me. I could taste my cum in her mouth and I started kissing her hard. We ended up fucking 2 more times before morning. Then spent the rest of the next day fucking and sucking our brains out only taking breaks for food and water. Terri was sucking my cock when my mother rang the doorbell to pick me up. I came down her throat and got my pants on as Terri opened the door thanked my mom for letting her use me and gave me a hug and a kiss on the cheek as I walked out with my mom. Terri and I spent a lot of time together that summer I would sneak out at night and she would come pick me up and we fucked like newlyweds.

She told me her husband has a very small cock and when she saw me she was amazed that my soft cock was about the same size as her husband’s was when he was hard. She had only had 5 sexual partners before me and 2 of them were women. She ended up divorcing her husband and we continued to see each other on and off even after we both married. She became very sexually active and eventually introduced me to several of her girlfriends. But those are stories for another day.

Fuck mom friend story

Memoirs of the Kosmetics Killer (Entry #6 and #7 Final)

Diary of the Kosmetics Killer (Entry # 6)

I was rather guilt ridden for a while after what I did to my pretty young and unsuspecting step niece. For a while, I tried to stop having dark thoughts about beautiful dead women but in the end, I could not control my lust. Two months after my step niece was drowned, I began to notice a very beautiful teacher working in a school nearby. She was beautiful in every way , sexy and graceful. She always dressed in a proper yet sexy manner which fuelled my desire for her all the more. For several weeks, I watched her every move and noticed that she leaves the school quite late on Thursdays for some reason. I therefore sneaked into the school one Thursday evening and proceeded to walk around to find her. The school was rather deserted by then. I was prepared to lie and say that I was a father looking for my son if anyone approached me but no one did.

Anyway, I spotted her walking out of her office towards the washroom at the end of the corridor. She was wearing a long black slinky sleeveless dress and she was looking really hot. I checked around to make sure there was no one around and no security cameras as well. I then walked towards the toilet and pushed the door open. She was standing with her back to me washing her hands but saw my reflection in the mirror. I only had seconds to act before she starts screaming and there was no time to prepare my chloroform or risk a karate chop which might not knock her out. I immediately ran forward, grabbed hold of her hair and pushed her head into a water trough in the washroom, probably meant for the cleaners to collect water. My other hand pushed down on her back to keep her body down.

She struggled hard but I managed to keep her head submerged and watched as her struggles grew weaker. The gurgling sound she was making, the scent of her perfume and the sensation of her body beneath my hand almost drove me mad with lust. After a couple of minutes, her hands fell limply to her sides and I could feel that she was dead weight in my hands. I pressed her head down in the water for a few more minutes before I pulled her head out of the trough and let her fall onto the floor with a thud.
Her face has turned ashen but she was otherwise still a beauty. She must have gulped down a lot of water because her belly looks bloated and was pushing uncomfortably against her tight dress. There was also water dribbling out from her open mouth. I removed her belt which looked ready to burst as it was not meant to be tied around a swollen belly. I then bent down to check and found that she was not breathing. This means that she is ready for me.

I locked the toilet door and pulled her dress halfway up. She was wearing a nice set of blue panties which I quickly pulled down. She was a neat person and her pussy was nicely shaved. I rammed my penis into her and started thrusting with urgency and speed as the school was not a very safe place for what I was doing. Every time I pushed forward onto her, my weight would push down on her stomach an water would spurt out from her mouth. I thought that this was very sexy so I placed my mouth over in a kiss. This way, all the water forced out by my movement would spray into my mouth. It tasted like tap water but slightly sour due to her gastric juices, I suppose. Still, it made my day to share a drink with such a beauty. Soon after, my cum sprayed into her still warm pussy.

I took a breather and admired her pretty face once more. Her face was now slightly bluish and her lips have turned slightly purplish. There was also frothy water streaming out from her open mouth. Looks like I have forced out water from her lungs as well as her stomach. I felt that since she has shared her drink with me, it is only right that I gave her a drink from me too. I placed my slowly hardening penis into her mouth and moved it in and out from her mouth. Her even, white teeth rasped against my penis, slightly painful but arousing. Soon, I could see her throat bulging with my fully erect penis. She gave me a truly great blowjob without a hint of gagging and my semen was soon flowing down her throat.

When that was done, it was time to work with the cosmetics. I pulled off her panties as a souvenir and rolled down her dress. I then used some napkins to wipe her face dry. I used some new violet coloured eye shadow on her with some purple mascara. Then I helped her apply some hot pink lipstick and blusher. She looked really great and somewhat alive. Then I quickly left the school compound.
Maybe this will be a lesson for teachers who are too beautiful and dress too sexy.

Diary of the Kosmetics Killer (Final Entry # 7)

After the teacher was found dead, the city was really in a panic. The Kosmetics Killer could now strike in a public place! I took my time to find my next target but it was getting increasingly difficult. 6 months later, it was random encounter one late afternoon at the supermarket which resulted in my next victim.
I was getting some groceries when I noticed a sexily dressed woman nearby. From the back, she looked svelte and sexy, with a white tank top with visible black bra straps. She was also wearing shorts that revealed her shapely thighs and legs. When she turned around, I was pleasantly surprised to find that she was actually heavily pregnant and her belly was bulging rounded and sexy and I could see the shape of her belly button pushed against her tank top. Her breasts were also enlarged by her pregnancy and were swollen with milk, and were appeared to be ready to spill out of her bra and top anytime. She did not have much makeup on other than some pink lip gloss but was the most beautiful pregnant woman I have seen since the baby shower victim. Looking at her face and sexy pregnant body, I nearly spontaneously ejaculated in my pants. I knew I got to have her.

I followed her out of the supermarket and saw her getting into her car alone. Looks like it has been too long since the last killing and the people are getting complacent. I drove and followed her closely until she arrived at her house. There were no lights on so there was probably no one at home. She opened the door and walked into the house.. I went up to the house but could not find an unlocked door or window anywhere. This means I have to try the frontal approach. I quickly took out my trusty bottle of chloroform which I have used before on my step niece and always keep on me for emergencies like this, and soaked a piece of cloth with it. I then went u to knock on the door.

Luckily enough, the mother to be opened the door, probably thinking that it was some neighbour or her husband. I pressed the cloth against her face and pushed her into the house while pressing her head into the cloth with my other hand. She punched and twisted but I was too strong for her. Soon, she slumped unconscious into my arms, her lips slightly parted and looking really lovely. I lay her onto the floor and decided that I would try a new method of killing today. Smothering.

I kissed her on her lips and felt her last breath n my cheeks and then I pinched her nose shut while covering her mouth with my other hand. I slowly crawled onto her and lay down on her pregnant belly while continuing to smother her. To my surprise and unease, I felt her baby kicking me though its mother’s belly. It won’t do him any good, I thought sadly. It’s his (or her) mother’s fault for being too hot and beautiful. The kicking soon stopped and I noticed that the woman’s face has turned bluish. I slowly released my hands and heard her final sigh as her last breath of air escaped from her nose and mouth. It sounds like she was urging me on.

I held up her pregnant body and pulled her top off. She was wearing a black bra which could barely contain her milk filled breasts. And I saw her round, pregnant belly it its full naked glory. It looked really large and swollen and I could not help but to kiss, lick and stroke it. I also squeezed her breasts and sucked on her nipples, tasting her still warm and sweet milk. I even let her try some of her own milk by kissing her after I suckled and spitting some milk back into her mouth.
I decided that it was too risky to have sex with her as I was for once unsure if anyone would be back. So I contented myself with inserting my penis into her mouth and within seconds, she has been impregnated orally with my seed. The sight of her throat bulging as my cum shoot into her is something I would never forget.

I decided to apply make up on her quickly before any one arrives. I held up her cooling body and pulled the tight fitting tank top back over her body. I then started on my make up. For her, I selected a hot red lipstick, light purple eye shadow, blue mascara and black eyeliner. She was gorgeous.

Suddenly, I heard a sound from upstairs. Before I could react, a heavily built man came down the stairs and saw what I was doing to his dead wife. To cut a long story short, her husband was sleeping above the whole time and he caught hold of me, beat me up and tied me to a chair before checking on his pregnant wife. Maybe he could have saved her if he tried to resuscitate her straight away but I must say that I enjoyed the sight of him giving his wife’s corpse intense but futile CPR, mixed with lots of kissing, caressing and crying on his part. It was so erotic and arousing that I did not mind when he came over and beat me nearly to death.

Now I sit on death row, with nothing to do but fantasize about my 8 lovely victims and writing my memoirs. I hope you have enjoyed reading it as much as I have writing and drawing it.