First Time Sucking A Cock
My mother had a friend, who was like her, divorced she had a son a year older than me. His name was Tim. Whenever one of these women needed to have time alone, we'd be sent for a weekend or overnight at the other's house. Her son and I were friends because of their relationship.
I was staying at their house for a couple days, I was 18. Tim and his mom lived in a very large old house in the city. It had 4 or 5 bedrooms, 3 floors. It was way too big for just two people, but she came from money, so they lived in this big old house. In his bedroom there were two closets, one was full of his stuff and the other his mother used for her overflow. I soon learned every other closet in the house was used for her overflow, she never threw anything away. We were alone in his bedroom and I looked inside his mom’s overflow closet, it was full of beautiful dresses and shoe boxes. Just by looking at it, I could feel my cock getting hard. I knew that I would have to look inside every one of those boxes to see the shoes they contained. Mrs. Wilson was always dressed to the nines and always wore very high heels just like my mom. I always paid attention to what women wore just in case I might find myself in a situation where I could try their things on and if they were my kind of high heels in those boxes, I would have to find a way to be alone with them so I could put them on and prance about the house like the lady in charge. The boxes that I could see were all marked size 8 and that was my size, I knew that for sure, I had out grown my mom’s a while back and she was a 7. I just had to find a time to be alone in the bedroom. It was a complete necessity an obsession and there was no way I was not going to check out her shoes and dresses and bras and girdles and stockings and slips and bathing suits. I loved to wear bathing suits and high heels, but I digress.
One morning, his mother came into his bedroom and woke us up, said she was leaving for the day and wouldn’t be back until dinner time or later and we should make our own breakfast and lunch and maybe even dinner, hang out and have some fun. When I heard her car, I got up and looked out the window to make sure she was driving away.
The desire to try on the shoes in those boxes was so strong, I didn’t care, I ran to the closet and grabbed a box, and opened it to find a beautiful pair of very high heel stilettos. They were my favorite style with a pointed toe and at least a 5-inch heel, I remember this pair as green leather with a paisley pattern and a bow on the back of the heel. I put them on and tried to make sort of a joke about it, but I kept them on and was walking around the bedroom. Tim thought this was very funny and suggested I try on one of her dresses. So, I went back to the closet to picked out a dress and that’s when I noticed I was hard as a rock. Tim noticed the tent in my pajamas too. He came over to me. I don't remember even being embarrassed, I'm sure I wasn't. He asked if he could see my hard dick, I pulled off my pajama bottoms. My dick popped out. Just the thought of wearing a pair of high heels always made me hard as a rock. I noticed he was getting a tent in his pajamas so I asked him if I could see his hard dick. He took off his pajama bottoms and his dick sprung out, it was longer and thicker than mine. Even at 18 I was completely unexperienced; I had never even kissed a girl. At 5 feet 4 inches and 105 pounds. I was not the focus of any girls attention and it never bothered me. I thought his cock was really kind of pretty, so hard and long and veiny with a big head. At that moment I was experiencing sexual attraction for the very first time in my life. All I wanted was to touch his hard cock, I wanted to lick it, kiss it, and most of all for some reason I wanted to have it in my mouth? He thought that my dick might be harder than his and asked if he could touch mine to see, I said SURE, OK. He put his hand around my cock, the feeling was instantly, wonderful and amazing. Without thinking I reached out and did the same to him, I put my hand around his hard cock we were standing face-to-face holding each other’s hard dicks. Him 19, me 18, I don’t know how it was possible but we both got even harder. I really didn't know what to do next until he kissed me. I hadn’t had any real experience with kissing. But I caught on fast and I liked it, I like it a lot, so I kissed him back. Instinctively both of us started to stroke the others cock up and down, but now we were also quite passionately kissing too.
He let go of my dick stepped back and said that he had seen a picture of a woman giving a blow job. He asked me if I knew what a blow job was, I said yes but I wasn't completely sure, but I hoped it had something to do with putting a cock in our mouth because that thought was becoming my foremost desire. He knelt down before me and kissed the tip of my dick I don’t know how I didn’t just cum in his face right at that second. He licked my dick up and down, he took it in his mouth and sucked it. After a few minutes, he stopped, he stood up he asked me if I would blow him, I was way ahead of him and immediately dropped to my knees and took his cock in my mouth. After just a few seconds I was sucking him for all I was worth. I licked his shaft, I lick his nuts, I sucked them into my mouth, I was almost swooning, I was so loving his ball sack in my mouth. I was a fast learner, I went back to hid hard dick, up and down, up and down up and down. We took turns until we realized we could lay down on the bed and both have a cock in our mouth. We figured out 69. We took a break; I went to his mother’s bedroom and found her lingerie. I was in heaven. I could have stayed all day in there just trying on her clothes and high heels, but now I knew about big penises and there was a hard one waiting for me down the hall. I put on her garter belt, stockings and a bra. The garter belt was red satin and lace with three belts on each leg. The stockings were dark with seems up the back. The bra was a old style rigid padded torpedo bra and but the looks of her drawer I think that's all she wore. The drawer was full of them. his mom must have been a D cup, I put one on again red satin and lace and came back wearing just her high heels, garter belt, stockings and a stuffed D cup bra. I walked up to him knelt and lick the big head of his still hard cock before I took into my mouth and pushed it against the back of my throat. I was falling in love with cock sucking. I must have blown him for 45 minutes. I took my time and tried anything I could think of. I remembered ever thing that made him groan, so that I could do it again later. He rubbed his cock on my face, he slapped my cheek with it and he put his hands on both sides of my head and pushed his hard dick in and out of my mouth. My first face fuck!
I must’ve been doing something right because I felt him tense and then explode in my mouth. I really was not expecting how much he came, having had no experience before, my head came back his cock came out of my mouth, he came in my mouth and all over my face. Once I tasted jizz I was hooked on that too. I wanted more. After that first experience, we saw a lot of each other, seemed like a couple times a week after school when his mom wasn’t home. We would go to his bedroom, we'd both get naked, I would put on a pair of high heels and a bra, kneel before. He'd put his cock in my open mouth and I'd feel it get hard in my mouth, I love that still today. It was after a few sessions that I finally came with my cock in his mouth, he swallowed like I had been doing, we had so much fun! We did this regularly until he went to college.
I think back and I remember those breakout sessions kissing our hands all over each other, kissing and hand jobs that always led to a long blowjob session. It wasn't that I didn't like girls, I just liked being one for a bit, with pretty lingerie, stockings and high heels and oh yes, a big dick to suck.
When he was 27, he got engaged, my mother and I were invited to the wedding. It was out of town and we had to stay at a hotel. His mother and my mother shared a room and I had a room to myself down the hall. I brought with me a pair of high heels, panties and a bra, I knew I'd be alone and thought it might be fun to be to dress up in a hotel and beat off.
I was supposed to meet my mom for lunch so I didn’t have to get up terribly early but I did because there was a knock at my door. It would be the last time we would be intimate. Tim had grown to a tall lean man and I had remained 5 foot 4 inches just the same as when I was 15. I heard the knock, I went to the door looked through the peephole and saw him, I immediately got an erection. I let him in and took off my pants, he smiled so I went and put on the pink leather high heel stilettos, panty and bra set I had brought. He had me do a little spin to show him what a sissy I still was. He knew for his cock I'd humiliate myself however he wanted. He said I still had beautiful legs and great taste in high heels. I walked over knelt before him and one last time sucked his cock. His cock was bigger than I remembered and he could hold out longer, which was OK with me because I loved to have his dick in my mouth for as much time as possible. I licked up and down the shaft, sucked his balls and ever turned him around and rimmed him. I had developed a real thing for the head of cocks and like to spend a lot of time showing my appreciation of them to whatever guy had his dick in my mouth at the time. He responded well to my new refined talents and eventually came and came. I didn't swallow until I showed him his huge load in my mouth and then gulped it down. I clean him up and zipped up his pants. Wow did I ever love that! He said it was the best wedding gift he had received and it would always be his favorite. I remember it so well, he had the best tasting cum.
I was staying at their house for a couple days, I was 18. Tim and his mom lived in a very large old house in the city. It had 4 or 5 bedrooms, 3 floors. It was way too big for just two people, but she came from money, so they lived in this big old house. In his bedroom there were two closets, one was full of his stuff and the other his mother used for her overflow. I soon learned every other closet in the house was used for her overflow, she never threw anything away. We were alone in his bedroom and I looked inside his mom’s overflow closet, it was full of beautiful dresses and shoe boxes. Just by looking at it, I could feel my cock getting hard. I knew that I would have to look inside every one of those boxes to see the shoes they contained. Mrs. Wilson was always dressed to the nines and always wore very high heels just like my mom. I always paid attention to what women wore just in case I might find myself in a situation where I could try their things on and if they were my kind of high heels in those boxes, I would have to find a way to be alone with them so I could put them on and prance about the house like the lady in charge. The boxes that I could see were all marked size 8 and that was my size, I knew that for sure, I had out grown my mom’s a while back and she was a 7. I just had to find a time to be alone in the bedroom. It was a complete necessity an obsession and there was no way I was not going to check out her shoes and dresses and bras and girdles and stockings and slips and bathing suits. I loved to wear bathing suits and high heels, but I digress.
One morning, his mother came into his bedroom and woke us up, said she was leaving for the day and wouldn’t be back until dinner time or later and we should make our own breakfast and lunch and maybe even dinner, hang out and have some fun. When I heard her car, I got up and looked out the window to make sure she was driving away.
The desire to try on the shoes in those boxes was so strong, I didn’t care, I ran to the closet and grabbed a box, and opened it to find a beautiful pair of very high heel stilettos. They were my favorite style with a pointed toe and at least a 5-inch heel, I remember this pair as green leather with a paisley pattern and a bow on the back of the heel. I put them on and tried to make sort of a joke about it, but I kept them on and was walking around the bedroom. Tim thought this was very funny and suggested I try on one of her dresses. So, I went back to the closet to picked out a dress and that’s when I noticed I was hard as a rock. Tim noticed the tent in my pajamas too. He came over to me. I don't remember even being embarrassed, I'm sure I wasn't. He asked if he could see my hard dick, I pulled off my pajama bottoms. My dick popped out. Just the thought of wearing a pair of high heels always made me hard as a rock. I noticed he was getting a tent in his pajamas so I asked him if I could see his hard dick. He took off his pajama bottoms and his dick sprung out, it was longer and thicker than mine. Even at 18 I was completely unexperienced; I had never even kissed a girl. At 5 feet 4 inches and 105 pounds. I was not the focus of any girls attention and it never bothered me. I thought his cock was really kind of pretty, so hard and long and veiny with a big head. At that moment I was experiencing sexual attraction for the very first time in my life. All I wanted was to touch his hard cock, I wanted to lick it, kiss it, and most of all for some reason I wanted to have it in my mouth? He thought that my dick might be harder than his and asked if he could touch mine to see, I said SURE, OK. He put his hand around my cock, the feeling was instantly, wonderful and amazing. Without thinking I reached out and did the same to him, I put my hand around his hard cock we were standing face-to-face holding each other’s hard dicks. Him 19, me 18, I don’t know how it was possible but we both got even harder. I really didn't know what to do next until he kissed me. I hadn’t had any real experience with kissing. But I caught on fast and I liked it, I like it a lot, so I kissed him back. Instinctively both of us started to stroke the others cock up and down, but now we were also quite passionately kissing too.
He let go of my dick stepped back and said that he had seen a picture of a woman giving a blow job. He asked me if I knew what a blow job was, I said yes but I wasn't completely sure, but I hoped it had something to do with putting a cock in our mouth because that thought was becoming my foremost desire. He knelt down before me and kissed the tip of my dick I don’t know how I didn’t just cum in his face right at that second. He licked my dick up and down, he took it in his mouth and sucked it. After a few minutes, he stopped, he stood up he asked me if I would blow him, I was way ahead of him and immediately dropped to my knees and took his cock in my mouth. After just a few seconds I was sucking him for all I was worth. I licked his shaft, I lick his nuts, I sucked them into my mouth, I was almost swooning, I was so loving his ball sack in my mouth. I was a fast learner, I went back to hid hard dick, up and down, up and down up and down. We took turns until we realized we could lay down on the bed and both have a cock in our mouth. We figured out 69. We took a break; I went to his mother’s bedroom and found her lingerie. I was in heaven. I could have stayed all day in there just trying on her clothes and high heels, but now I knew about big penises and there was a hard one waiting for me down the hall. I put on her garter belt, stockings and a bra. The garter belt was red satin and lace with three belts on each leg. The stockings were dark with seems up the back. The bra was a old style rigid padded torpedo bra and but the looks of her drawer I think that's all she wore. The drawer was full of them. his mom must have been a D cup, I put one on again red satin and lace and came back wearing just her high heels, garter belt, stockings and a stuffed D cup bra. I walked up to him knelt and lick the big head of his still hard cock before I took into my mouth and pushed it against the back of my throat. I was falling in love with cock sucking. I must have blown him for 45 minutes. I took my time and tried anything I could think of. I remembered ever thing that made him groan, so that I could do it again later. He rubbed his cock on my face, he slapped my cheek with it and he put his hands on both sides of my head and pushed his hard dick in and out of my mouth. My first face fuck!
I must’ve been doing something right because I felt him tense and then explode in my mouth. I really was not expecting how much he came, having had no experience before, my head came back his cock came out of my mouth, he came in my mouth and all over my face. Once I tasted jizz I was hooked on that too. I wanted more. After that first experience, we saw a lot of each other, seemed like a couple times a week after school when his mom wasn’t home. We would go to his bedroom, we'd both get naked, I would put on a pair of high heels and a bra, kneel before. He'd put his cock in my open mouth and I'd feel it get hard in my mouth, I love that still today. It was after a few sessions that I finally came with my cock in his mouth, he swallowed like I had been doing, we had so much fun! We did this regularly until he went to college.
I think back and I remember those breakout sessions kissing our hands all over each other, kissing and hand jobs that always led to a long blowjob session. It wasn't that I didn't like girls, I just liked being one for a bit, with pretty lingerie, stockings and high heels and oh yes, a big dick to suck.
When he was 27, he got engaged, my mother and I were invited to the wedding. It was out of town and we had to stay at a hotel. His mother and my mother shared a room and I had a room to myself down the hall. I brought with me a pair of high heels, panties and a bra, I knew I'd be alone and thought it might be fun to be to dress up in a hotel and beat off.
I was supposed to meet my mom for lunch so I didn’t have to get up terribly early but I did because there was a knock at my door. It would be the last time we would be intimate. Tim had grown to a tall lean man and I had remained 5 foot 4 inches just the same as when I was 15. I heard the knock, I went to the door looked through the peephole and saw him, I immediately got an erection. I let him in and took off my pants, he smiled so I went and put on the pink leather high heel stilettos, panty and bra set I had brought. He had me do a little spin to show him what a sissy I still was. He knew for his cock I'd humiliate myself however he wanted. He said I still had beautiful legs and great taste in high heels. I walked over knelt before him and one last time sucked his cock. His cock was bigger than I remembered and he could hold out longer, which was OK with me because I loved to have his dick in my mouth for as much time as possible. I licked up and down the shaft, sucked his balls and ever turned him around and rimmed him. I had developed a real thing for the head of cocks and like to spend a lot of time showing my appreciation of them to whatever guy had his dick in my mouth at the time. He responded well to my new refined talents and eventually came and came. I didn't swallow until I showed him his huge load in my mouth and then gulped it down. I clean him up and zipped up his pants. Wow did I ever love that! He said it was the best wedding gift he had received and it would always be his favorite. I remember it so well, he had the best tasting cum.
3 years ago
