Having Sex With Big Lou, My Dad's Best Friend
I had turned 18. I was in my last semester of high school. I was a young white teen in a middle-class suburban home. My parents had some friends who had three small c***dren. My parents and these friends would all go out dancing and socialize together. Unfortunately this other couple, Lou and Mary, needed a baby sitter to watch their k**s or they couldn’t go out – my mother volunteered me.
I felt that I was too old to be babysitting. I had a regular job after school every weekday and on Saturdays. However, my parents and their friends Lou and Mary Palermo only went out on Saturday night. I didn’t have an excuse other than telling my friends that I couldn’t go out with them. I didn’t have a steady girlfriend even though I had an occasional date. It still felt humiliating babysitting. I had done that in junior high. I felt like a grownup, not a c***d!
My dad forced me to baby sit. Lou and Mary were of Italian heritage from New Jersey. Lou always reminded me of a wise guy in the Mafia. I never said anything to my parents, but I thought his background was suspicious - and an Italian from New Jersey! Anyway, my parents drove me to the Palermos’ house the first time that they had me baby sit. It was an uneventful night and Mr. Palermo gave me $40 for the four hours that I babysat – More than fair. That changed my impression of Mr. Palermo. I thought he was an okay fair man. I began to like him. He was kinda cool with the Jersey accent and he was a stocky, powerfully built man. He looked like a Mafia boss, but he was a nice man!
Several weeks went by and my parents and the Palermos made it a weekly thing, but it was out of the way for my parents to pick up the Palermos, so the Palermos volunteered to take their own car and meet my parents at the lodge that they went to. Both my dad and Mr. Palermo were members. The Palermos came and picked me up and then dropped me off at their house to baby sit, which meant Mr. Palermo also drove me back home. It was this first time alone with Mr. Palermo driving me home that I had my first gay sexual encounter.
Maybe it is because of my looks. I am 5’11” and *******5 pounds. I have shaggy long brown hair and kind of a high voice, but as Mr. Palermo drove me home he unzipped his pants and began asking me strange questions. He asked me if I liked pipe! I replied, “pipe?” “Pipe, dick, cock?” He asked me if I sucked dick! I said no! He then pulled out this huge penis. It was twice as long as mine; it looked over 9-10”! Their car was an older Cadillac with a large bench front seat. He told me to "move closer and touch my cock!" I was in shock. I couldn’t believe what Lou, my dad’s closest friend, was saying! I don’t know why, I guess I was brought up to respect my elders and do what they asked, so I slid over beside him. He was an intimidating figure, 6’1” 245 pounds, large, powerfully built man. I reached over and played with his cock as we drove. I couldn’t believe how it felt in my hands. I marveled at its massive size, smoothness and blood vessels bulging on it.
I caressed it and stroked him. He told me “good boy!” Instead of continuing to drive home, he drove into this city park. It was about midnight and pitch black. We were the only car in the parking lot. He pulled up, parked, and turned off the engine. With only a little light from a street lamp across the parking lot I could see the outline of his big cock. It was already half hard. “Suck me, son!” I did exactly what he asked. I bent over and went down on him. It was weird in the quietness and the still of the night in the front-seat leather interior taking the head of his big dick in my mouth.
I began sucking on him as best I could. I mean, this was a big cock, meaty, long! It got harder as I pleasured him. He moaned and gave me words of encouragement. I sucked my first dick and it was my dad’s best friend's. Wouldn’t my dad be surprised if he knew what I was doing? I actually found pleasure in sucking on him. It was like a cock this big deserved to be worshiped! I took more and more of him into my mouth and down my throat. I gagged trying to breath with this monster down my throat.
As time went by I managed to relax and take most of him down my throat. I bobbed and bobbed as he sighed and told me to keep sucking daddy’s big dick. Then after ten minutes or so his dick throbbed in my mouth. Then I felt it begin squirting hot semen down my throat! Lou reached over and held my head down on him as he ejaculated the remaining cum down into my gut. I gulped and gulped swallowing every last drop! Then it was over. Lou told me “good boy! You are a natural cocksucker! Don’t tell anyone! You understand?” I nodded my head yes, I understood. He could kill me in two seconds. Anyway, I actually enjoyed this! I know I couldn’t believe this myself! My own dick was rock hard and I actually had an orgasm as I sucked him!
Lou drove me on home. He gave me his pager number and told me to call him whenever I wanted to suck his dick again. I thought that this was probably going to be a one-time event. It couldn’t continue, but it did. After a few days that was all I could think about, Lou’s giant penis and me sucking on him. I was ashamed and racked with guilt. What would others say or think if they knew I was a cocksucker for my dad’s best friend? I went into the bathroom and beat off with images of Lou’s cock in my mind. I couldn’t get him out of mind. I wanted to do it again.
Sure enough, the same scenario happened the next Saturday night. Mr. Palermo came and got me to baby sit their three k**s again. Four hours later the Palermos returned home and he drove me back home. This time he asked me if I wanted to suck him again and I nodded my head yes. He drove to the park and parked. I devoured his cock, helping him unzip his fly – I had to have it in my mouth. This time, however, as I sucked on him, I felt his hand slip down into the back of my pants. I felt his cold hand on my bare bottom. He began to insert his large fat finger into my hole. He worked it deeper and deeper into my pucker. It felt really good, better than I could have imagined. As he fucked my hole with his finger, I sucked on his large daddy dick, all 10”. I came in my pants two or three times! It was the best sexual experience that I had ever had up to that point. It felt incredible having him fuck me with his finger and then he added a second finger, working my opening stretching it larger and larger.
Then I felt his huge penis explode down my throat. Again I gulped down all of his gooey cum! This time with his fingers still in my ass I was so much more turned on. As he drove me home, he again reiterated for me to call his pager (this was 30 years ago, before cell phones). He then asked me if I had ever caddied for a golfer before. I said that I had for my dad. He then said that what we could do is get a motel room and pretend that I would caddy for him and instead of playing golf have sex in the privacy of a hotel room. I agreed to going with him to a motel or hotel room and have sex instead of a golf game.
The next Sunday my dad, who sometimes plays golf with Lou, was out of town and wouldn’t be back for almost a week. Lou called and asked my mom if it was okay for me to caddy for him Sunday. She told him, “sure, if he wants to!” Of course I was eager to caddy for him, because I knew we were going to have sex in his hotel room. Lou got us the hotel where he booked his business partners and he could write it off. He had told me it would be better if I cleaned myself thoroughly and brought some lube.
So Sunday morning came and Lou picked me up. We ended up at the hotel. To not draw suspicion Lou got the room and came down and told me the room number. I followed up to his room a few minutes later. And as soon as I got in there he had me get naked and my rear was already clean and lubed. I sucked him hard and he fucked me with his huge 10” thick meaty monster. It hurt at first. He went slow and in a few minutes had it buried in me. He began fucking me. It felt incredible even much better than with his fingers fucking me.
I whimpered at first and moaned as he pounded my rear. He got more and more rough and soon he jack hammered my rectum. Even though it bruised me, it felt so incredible. Even though Lou was a large stocky Italian, he was powerfully built and was more flexible than anyone could imagine. He loved fucking my tight hole! He even had me face him; he pulled my legs apart buried his cock in me and dragged me to the edge of the bed. He then picked me up off of the bed, fucking my hole bouncing me up and down on his stiff giant phallus. He confessed that his wife didn’t like sex and hated sucking his huge penis and he never fucked her in the ass. He told me that my ass felt incredible wrapped around his cock. He called my ass his honey hole and boy did he enjoy fucking it! It got to where I was sneaking out several times a week and meeting Lou at the hotel for sex. I craved his cock and he likewise craved my anus. I had kinda of a bubble butt; I had no hair on my legs or body except for my pubic hair, which he had me shave. For all practical purposes I looked like a girl with a smooth hairless body and a feminine-looking rear, and boy did Lou love to fuck me! We carried on for several years. Lou’s wife was suspicious that he was having an affair with another woman because they stopped having sex altogether. He preferred me, which made me feel proud until the private eye that Mary hired took photos of me and Lou having sex and reported that back to his wife. Needless to say, she divorced him and my parents found out about me having sex with Lou and they kicked me out of the house!.
All is not bad for now. I live with Lou in his new townhouse and we have sex every day. I still don’t know if Lou is connected and in the mob! He has brought several mob-like guys home and they all gang fucked me all night long! I love it and love Lou and his big daddy cock!
I felt that I was too old to be babysitting. I had a regular job after school every weekday and on Saturdays. However, my parents and their friends Lou and Mary Palermo only went out on Saturday night. I didn’t have an excuse other than telling my friends that I couldn’t go out with them. I didn’t have a steady girlfriend even though I had an occasional date. It still felt humiliating babysitting. I had done that in junior high. I felt like a grownup, not a c***d!
My dad forced me to baby sit. Lou and Mary were of Italian heritage from New Jersey. Lou always reminded me of a wise guy in the Mafia. I never said anything to my parents, but I thought his background was suspicious - and an Italian from New Jersey! Anyway, my parents drove me to the Palermos’ house the first time that they had me baby sit. It was an uneventful night and Mr. Palermo gave me $40 for the four hours that I babysat – More than fair. That changed my impression of Mr. Palermo. I thought he was an okay fair man. I began to like him. He was kinda cool with the Jersey accent and he was a stocky, powerfully built man. He looked like a Mafia boss, but he was a nice man!
Several weeks went by and my parents and the Palermos made it a weekly thing, but it was out of the way for my parents to pick up the Palermos, so the Palermos volunteered to take their own car and meet my parents at the lodge that they went to. Both my dad and Mr. Palermo were members. The Palermos came and picked me up and then dropped me off at their house to baby sit, which meant Mr. Palermo also drove me back home. It was this first time alone with Mr. Palermo driving me home that I had my first gay sexual encounter.
Maybe it is because of my looks. I am 5’11” and *******5 pounds. I have shaggy long brown hair and kind of a high voice, but as Mr. Palermo drove me home he unzipped his pants and began asking me strange questions. He asked me if I liked pipe! I replied, “pipe?” “Pipe, dick, cock?” He asked me if I sucked dick! I said no! He then pulled out this huge penis. It was twice as long as mine; it looked over 9-10”! Their car was an older Cadillac with a large bench front seat. He told me to "move closer and touch my cock!" I was in shock. I couldn’t believe what Lou, my dad’s closest friend, was saying! I don’t know why, I guess I was brought up to respect my elders and do what they asked, so I slid over beside him. He was an intimidating figure, 6’1” 245 pounds, large, powerfully built man. I reached over and played with his cock as we drove. I couldn’t believe how it felt in my hands. I marveled at its massive size, smoothness and blood vessels bulging on it.
I caressed it and stroked him. He told me “good boy!” Instead of continuing to drive home, he drove into this city park. It was about midnight and pitch black. We were the only car in the parking lot. He pulled up, parked, and turned off the engine. With only a little light from a street lamp across the parking lot I could see the outline of his big cock. It was already half hard. “Suck me, son!” I did exactly what he asked. I bent over and went down on him. It was weird in the quietness and the still of the night in the front-seat leather interior taking the head of his big dick in my mouth.
I began sucking on him as best I could. I mean, this was a big cock, meaty, long! It got harder as I pleasured him. He moaned and gave me words of encouragement. I sucked my first dick and it was my dad’s best friend's. Wouldn’t my dad be surprised if he knew what I was doing? I actually found pleasure in sucking on him. It was like a cock this big deserved to be worshiped! I took more and more of him into my mouth and down my throat. I gagged trying to breath with this monster down my throat.
As time went by I managed to relax and take most of him down my throat. I bobbed and bobbed as he sighed and told me to keep sucking daddy’s big dick. Then after ten minutes or so his dick throbbed in my mouth. Then I felt it begin squirting hot semen down my throat! Lou reached over and held my head down on him as he ejaculated the remaining cum down into my gut. I gulped and gulped swallowing every last drop! Then it was over. Lou told me “good boy! You are a natural cocksucker! Don’t tell anyone! You understand?” I nodded my head yes, I understood. He could kill me in two seconds. Anyway, I actually enjoyed this! I know I couldn’t believe this myself! My own dick was rock hard and I actually had an orgasm as I sucked him!
Lou drove me on home. He gave me his pager number and told me to call him whenever I wanted to suck his dick again. I thought that this was probably going to be a one-time event. It couldn’t continue, but it did. After a few days that was all I could think about, Lou’s giant penis and me sucking on him. I was ashamed and racked with guilt. What would others say or think if they knew I was a cocksucker for my dad’s best friend? I went into the bathroom and beat off with images of Lou’s cock in my mind. I couldn’t get him out of mind. I wanted to do it again.
Sure enough, the same scenario happened the next Saturday night. Mr. Palermo came and got me to baby sit their three k**s again. Four hours later the Palermos returned home and he drove me back home. This time he asked me if I wanted to suck him again and I nodded my head yes. He drove to the park and parked. I devoured his cock, helping him unzip his fly – I had to have it in my mouth. This time, however, as I sucked on him, I felt his hand slip down into the back of my pants. I felt his cold hand on my bare bottom. He began to insert his large fat finger into my hole. He worked it deeper and deeper into my pucker. It felt really good, better than I could have imagined. As he fucked my hole with his finger, I sucked on his large daddy dick, all 10”. I came in my pants two or three times! It was the best sexual experience that I had ever had up to that point. It felt incredible having him fuck me with his finger and then he added a second finger, working my opening stretching it larger and larger.
Then I felt his huge penis explode down my throat. Again I gulped down all of his gooey cum! This time with his fingers still in my ass I was so much more turned on. As he drove me home, he again reiterated for me to call his pager (this was 30 years ago, before cell phones). He then asked me if I had ever caddied for a golfer before. I said that I had for my dad. He then said that what we could do is get a motel room and pretend that I would caddy for him and instead of playing golf have sex in the privacy of a hotel room. I agreed to going with him to a motel or hotel room and have sex instead of a golf game.
The next Sunday my dad, who sometimes plays golf with Lou, was out of town and wouldn’t be back for almost a week. Lou called and asked my mom if it was okay for me to caddy for him Sunday. She told him, “sure, if he wants to!” Of course I was eager to caddy for him, because I knew we were going to have sex in his hotel room. Lou got us the hotel where he booked his business partners and he could write it off. He had told me it would be better if I cleaned myself thoroughly and brought some lube.
So Sunday morning came and Lou picked me up. We ended up at the hotel. To not draw suspicion Lou got the room and came down and told me the room number. I followed up to his room a few minutes later. And as soon as I got in there he had me get naked and my rear was already clean and lubed. I sucked him hard and he fucked me with his huge 10” thick meaty monster. It hurt at first. He went slow and in a few minutes had it buried in me. He began fucking me. It felt incredible even much better than with his fingers fucking me.
I whimpered at first and moaned as he pounded my rear. He got more and more rough and soon he jack hammered my rectum. Even though it bruised me, it felt so incredible. Even though Lou was a large stocky Italian, he was powerfully built and was more flexible than anyone could imagine. He loved fucking my tight hole! He even had me face him; he pulled my legs apart buried his cock in me and dragged me to the edge of the bed. He then picked me up off of the bed, fucking my hole bouncing me up and down on his stiff giant phallus. He confessed that his wife didn’t like sex and hated sucking his huge penis and he never fucked her in the ass. He told me that my ass felt incredible wrapped around his cock. He called my ass his honey hole and boy did he enjoy fucking it! It got to where I was sneaking out several times a week and meeting Lou at the hotel for sex. I craved his cock and he likewise craved my anus. I had kinda of a bubble butt; I had no hair on my legs or body except for my pubic hair, which he had me shave. For all practical purposes I looked like a girl with a smooth hairless body and a feminine-looking rear, and boy did Lou love to fuck me! We carried on for several years. Lou’s wife was suspicious that he was having an affair with another woman because they stopped having sex altogether. He preferred me, which made me feel proud until the private eye that Mary hired took photos of me and Lou having sex and reported that back to his wife. Needless to say, she divorced him and my parents found out about me having sex with Lou and they kicked me out of the house!.
All is not bad for now. I live with Lou in his new townhouse and we have sex every day. I still don’t know if Lou is connected and in the mob! He has brought several mob-like guys home and they all gang fucked me all night long! I love it and love Lou and his big daddy cock!
5年前
