Many people would think a kid like me growing up as a chubby teenager with; well to be honest, a not so big cock never got laid. Sexually, I had it all since I was 15. The catch on this story? I got everything I needed at home. Fucking my sister Tammy was as easy and common as drinking a glass of milk. I gave her my virginity. Tammy was the first to suck my dick and swallow my cum. She was the first person I fucked. She was the first person I fucked anally. She is the first pussy I ever got to eat out. She is first girl I ever Frenched kissed. She is the first girl I ever got to tittie fuck. Her tits (38DD) are the first I ever sucked on and squeezed. She was the first person to let me cum on her face and tits. She is the first person I ever fucked in a car or in a pool. She was my #1 all around fuck buddy.
Now I am the oldest of 5 kids, with four younger sisters. I've never done or thought to do anything like this with any of my other sisters. To this day, I don't think anyone besides God know our secret (except you reading this). We come from a conservative Catholic family. For the record, I always think a Conservative up bringing back fire. Tammy was closes in age to me, we are just 12 months apart.
Tammy and I went to separate private Catholic schools. One for all girls and one for all boys, I was a junior and she was a sophomore. I came home one day from school and went to make a sandwich. It was a day I normally stay late after school for something but whatever the activity, it was unexpectedly cancelled this day. My three youngest sisters were always home a couple hours later from elementary school. And I don't remember specifics, but something I was looking for was gone from the refrigerator. I knew Tammy had to have taken it. Now like me, Tammy was always chubby too, but very attractive. She was your typical short chubby round Irish girl. She is short around 5 feet tall, short brown hair, and green eyes. Not obese by any means, just round around the edges. So, I went looking for her to let her to go off on her about my sandwich. I guess I was just in a bad mood coming home from school and needed a good old sibling fight. So I went looking for one. Tammy was always my favorite target to blow off some steam.
Instead of just yelling down to the basement where Tammy's bedroom was, I decided to do my yelling in person. I saw her book bag on the kitchen table so I knew she was home. I marched down the steps and over to her opened bedroom door. I walked in.
She was as shocked to see me, as I was to see her riding her boyfriend Jude's cock. After first she was going at a pretty good pace. She slowed down but didn't stop. Jude just continued to play with both of her tits as she rode. We locked eyes and stared. It seems we stared for half hour, but it was probably just 5 to 10 seconds. I had never seen her naked before. I was stunned she was sexual active. This was the last thing I expected to see. I didn't say anything as I quietly turned around and went back upstairs to eat. From his angle, I don't think Jude ever knew I was there. I don't think Tammy ever told him either. I got some food and retreated to my bedroom which was just off the kitchen, sort of isolated from the rest of the house.
Of course, I couldn't stop thinking about seeing my sister ride her boyfriend. My cock was so hard. I thought about them having sex in the basement. I was so jealous. I had yet to have sex. Tammy was 14 and getting a good lay. I wondered how long she had been sexually active. At 15 years old, it didn't take much to get hard and I was like morning wood. About 15 minutes later I heard them come up from the basement and Jude left. As soon as Jude left Tammy comes charging in my room, "Chip you fuck'n asshole. What the hell did you want! You better not say anything to Mom!" I am sure I called her every name in the book from slut to whore, etc. I had cursed at her many times before but never anything like this.
We always fought and cursed at one another. But, this wasn't just another sibling argument. I seem to be madder at her than ever before. I think I was jealous that she was younger and getting laid, and I wasn't. I think she knew it too. I knew I could get her in major trouble. She begged more and more for me not to tell. Of course she started crying. I was 15, never had a girlfriend. So I had no sympathy for a girl crying. She was doomed and she knew it. Her final plea was "I'll do anything." I had never thought about it but I just said a reflex response of, "Do me, right now, right here before Mom get's home or else. If you can fuck Jude, you can fuck me too."
She cursed and said she would tell Mom I said that. "You fuck’n sicko. I'm tell'n Mom you said that, you gross pig." she yelled. I knew she couldn't. Mom wouldn't believe her. I was the only son. The Golden Child. Mom always took my side. I knew it. Tammy knew it. I told her to get out. She stared for a minute and said "Fine, do you have condoms." I did not. I was stunned but didn't think she really would though. She said she wasn't having sex without a condom. Maybe she was a slut and whore, but she was a stright 'A' student. She knew what safe sex was, better than I. I thought this was her way out. I hadn't really thought about condoms before I demanded sex. She told me to lay down and take my pants off. I had no idea what she was going to do. Everyone remembers their first blow job because it's the first. But even back then, Tammy sucked cock like a world champion...a 14 year old cock sucker champ. Jude had taught her well. I am sure it took me only a minute or two to cum. Tammy swallowed every last drop. I always thought that swallowing cum was common. It's all I ever knew until later in life when I dated some prudes. As quick as she swallowed, she got up and left just as quick without a word. She said nothing and at dinner everything was normal as it gets in our house.
Two weeks later on a Saturday night, Tammy comes home in tears saying her and Jude broke up. This was not a rare event. I ignored it and she tells her sob story to our parents. Later that night around 12:30am I am just about asleep and I am startled by my door opening. Everyone in the house was asleep. Tammy bedroom was in the basement, mine on the first floor off the kitchen, and everyone else slept upstairs. Tammy walks-in and over to the bed. "Are you awake?" she asked. I turned over and looked at her. She took off her night shirt to reveal her round naked body. Her 38DD tits seemed bigger up close. I always could tell she didn't wear a bra or panties with her night shirt. She got into bed and we just laid next to one another in a spoon position. I am sure she could feel my wood thru my boxers. She turned over after a few minutes as asked me to finger her. So all I could figure was to put my finger in her pussy and wiggle it. But it was nice, soft, warm, and wet. I sucked on her tits and then moved up to lock lips. At this point I had totally stopped thinking this was my sister Tammy. I think at this moment I knew I would always be a breast man. Her tits were heavenly. Her nipples were larger and raised, not too dark, not too lite, colored like ham. After a few minutes she said "I need you inside me." I reminded her I had no condoms. She told me she was about to have her period and it was safe. So I climbed on and fucked her with my 5 inch cock. As my cock entered my sister pussy I remember how inch by inch my cock got warmer and warmer. She asked how it felt. As I said, Tammy has a round body but it was always tan. She tanned with a one piece bathing suit. I remember the joy of seeing her huge milky white tits away. I still love looking at those swaying milky tits today. I shot a huge load in her. She asked me to hold her while she played with herself until she came. I made sure to always have condoms in my drawer from then on.
Every Saturday night she would come in and we would fuck like that. Even weeks later when her and Jude got back together, we still fucked at least once a week but usually more. Some days if she had a bad day or I did, we'd fuck. Our code phrase was to ask if there was something good on TV. If the other person said yes, we were fucking. It was mutually understood to help the other person. I was so easy to fuck after school but I just had to wait until Jude had her first. Within 2 to 3 months we were fucking semi-regularly after school most days. It part of our daily routine. We became fuck buddies.
After a few months Tammy asked me if I wanted to try anal. I had no interest but what the heck. She said Jude wanted to but she was scared. She said he was much bigger than me. She wanted to try my cock in there first. I was awesome. I love anal. Our first time she layed flat on her belly. I put some Vaseline in her opening and slowly entered. At first she screamed a little. I went slow. In a minute she quickly adjusted and said she liked it. I layed flat on her, reached around to palm each tit, grabbed them hard, and fucked her ass as hard as I could with my 5 inch cock. Tammy always had a big pussy, so anal was a nice change. It took about 5 minutes to cum in her ass. Eventually she let Jude, but I was the first in her ass.
I remember one Saturday night when she came home from a date with Jude. It was common for Tammy to go out on a date, suck and fuck Jude, and then come home to fuck me. Tammy came in that night and said she was sore. She said Jude's gotten into tying her up with rope, and fucking her hard. She said he's really gotten in rough dirty sex and cuming on her face. She said she loved it but it was very hard. She was too sore to fuck. I asked if I could eat her out. She said she thought I would never ask. She said she thought I wasn't into that. I remember the first time I tasted her. I could smell the condom that had fucked her pussy just an hour ago. Eventually we got into a 69 and made each other cum.
Later that spring our parents went to a wedding and took our sisters. We planned this weekend for months. We decided to sleep together in our parents’ bed. I told Tammy I wanted to try using ropes like she did with Jude. Tammy was all into it. This is when she first asked me to talk dirty to her. She wanted me to refer to her as my whore. "Fuck your whore's cunt" she liked to say. She says it to this day. This was also when I learned that after you fuck once, and fuck again right away, the second time you last longer. We fucked 4 to 5 times a day that weekend. Tammy was the first girl I ever slept naked with over night. This weekend, We had sex in every room, on everyone's bed, and on over couch. I remember tying her to the kitchen table and eating her out. We showered together in our parents bathroom. This was the same weekend when I came on her face for the first time. She asked me to and I was all into it. I asked her why she wanted me to do that. She said it was my mark that she was my whore. Sounded good to me. I think Jude left his mark there too, plenty of times.
Tammy dated Jude all thru high school. We fucked on a regular basis the entire time. We remained loyal fuck buddies. I did eventually get a girl friend the next year right before graduation. I asked Tammy for a quickie fuck right before my prom in case I got lucky and would not pop right away. Tammy thought it was a good idea. It was nearly impossible to fuck in house with everyone home. It was very risky and we never did it. But it had to be done. We just said she was helping me with my bow tie for my tux. I think we fucked for three minutes before I came. I fucked her doggie style with most of her clothes still on, just in case we heard someone coming. He just pulled her pants down to her ankles and bent over the bed. I left for the prom and it paid off. Tammy was happy for me.
I went off to college and Tammy would visit. I had an apartment with three friends. We each had our own room so I would tell them Tammy was sleeping on the coach in my room. I guess it seemed normal to them. None of my roommates had interest in Tammy. We fucked like crazy but quietly in the apartment. I think Tammy came to visit like every other week. I made rare visits home during breaks.
The next year Tammy went off to college and got a new boy friend that she would eventually marry. I would visit her at college but she had a typical dorm room. So we had to settle for car sex. Tammy was the first girl I fucked in a car.
Summer breaks during college were filled with sex 2 to 3 times week. College didn't stop us from being fuck buddies. Her boyfriend would visit over the weekends during the summer. so, I would make sure I get my pussy in during the week.
Sometimes she'd fuck her boyfriend in her room and then come see me right after. Some time she'd still have cum on her tits or in her cunt without showering and come directly in to fuck me. She'd tell her boyfriend that she was going to take a long shower to clean off his cum, but stop by for a quickie. She was loyal like that. We treated sex like a hobby shared between friends. Why not?
Eventually we both got married. Tammy first. I remember the night before her wedding she stayed at our parents house, where I was still living after college. We fucked all night. I came three times - first in her mouth, then in her ass, and then in her cunt. To this day, we both agree it was the best sex we had together. She returned the favor when I got married a few years later. I got a sick joy seeing her on the altar knowing I had nailed her that night and earlier that morning.
Soon after they married Tammy and hubby bought a house. Tammy's husband worked about an hour away. I worked in the same town where they lived. It was easy to stop by on the way for a fuck and be out before hubby arrived home. Sometimes I would go over, fuck Tammy at her hour, and they stay around where we'd have dinner. From time to time Tammy and would even shower together before hubby arrived home. Tammy had a pool. We got to skinny dip and fuck from time to time in the pool most times when her hubby went away on business I would sleep over.
One time, and I stress one time, after I had come over for a good 15 min fuck, hubby came home and all three of us hung out by the pool. We got wasted. They wanted to go swimming and of course I didn't have a bathing suite. Hubby and I were not the same size. I told them I was just going to leave. They said I was too drunk to leave. Tammy goes, "I'll turn the lights out by the pool. We don't need bathing suits." Their backyard was very private to neighbors. I didn't know what to do. I knew I had to act odd or uncomfortable about this but in reality I had been fucking my sister for years. Heck I just fucked her two hours ago. Tammy just stripped and went in the pool. Hubby just shook his head. Then he goes, I don't think you want to know how wild your sister can be. I just laughed a little and thought about what he meant. So I waited a minute and then we both joiner her. It was a hot night; I had been drinking for hours, so the pool was a welcome comfort. I was comfortable with the e fact that hubby was about my size 4 to 5 inch cock. We were both hard. Hubby started making sexual references making Tammy laugh. The one comment he made that made me almost crap in the pool was when he goes, "I bet you’re not crazy enough to do a threesome with your brother." I laughed but then it dawned on me that I guess they have done threesomes. So I prodded them a little because I knew Tammy wouldn't tell me anything alone. I asked if they had done threesomes. They were drunk so I was expecting full confessions. The both laughed. Hubby explained they weren't swingers but did threesome or gang bangs from time to time since college. I was taken back. I was speechless and oddly quiet. Tammy seemed uncomfortable that I had found this out. I just responded with "Whatever makes you guys happy." Hubby says to Tammy, "you can at least blow chat and I tonight, can't you." She goes "That's my brother and I doubt he wants to hear this! How would you like to talk to your sister like this?" I had to respond, "Its okay. I don't mind." I wanted it all out. I thought we were close but now I had come to learn there was this other side of Tammy's sex life for years without me. As hubby started to share stories the only way to get him to shut up was to start blowing him. I tried to act uncomfortable with seeing my sister suck cock, but it was hard. It was actually a turn on. They both asked me if I wanted one. I knew I had to resist at first, but I made that a feeble attempt. I could believe she was sucking me in front of hubby. We grabbed a towel and went on to the grass. We took turns fucking her while she layed on her back blowing the other. We fucked like this for about 45 min until we came in her. After we came, Tammy played with her pussy to cum. We each sucked her tits until she came. I got up, dressed, said good bye, and left. He never caught on that we were ongoing fuck buddies. I never spoke to either of them about that night. Tammy and I never had a threesome or any type of group sex again. We remained 1:1 fuck buddies.
We still fuck today; even though, Tammy and family live out of state. She comes home for family visits. We might fuck over the pool table, in the car, real quickies wherever and whenever we can fit it in without much risk. Tammy prefers it in her ass these days so her husband doesn't smell my cum in her cunt. These days it's usually either her ass or her mouth. Last month I took my family out to visit them. We'd stayed up after everyone and I got to fuck her doggie in her family room where her hubby had watched football that day earlier. We're in our late 30s today and sex is just as good as when we started fucking as teenagers, just not as often.