Teaching A First Timer free porn video

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I am a 50 year old man who likes both men and women. I have been with a few guys before but this story is about me being someones first. It was summer time and I was lonely and needed some company. I was looking through craigslist and I came across an ad where this young man was looking for someone to be his first in gay sex. He had posted a picture of his dick and it looked really tasty. I did not know if he would be interested in an older guy or not since he did not say an age so I decided to write him anyway to see what happened. I sent him an email saying I would love to be his first and teach him everything about man on man sex. Now I have a 8" dick that I like to have sucked and his looked like it was that big or bigger maybe 10" I really wanted to find out. So I waited and he wrote me back. He said he was interested in meeting me and thought I would be a good first guy for him. So we set up a day to get together. I was looking forward to our play date.
The day cam and he showed up right on time. I answered the door and found a young man of about 28 standing in front of me about 6'2" average build and a nice smile. I asked him in and we sat down and started to talk. He said," I will be honest I am a little nervous as I said in my ad I have never been with a guy before." I told him, " I understand and do not worry I will go slow and make sure you have a really good time today." He seemed to become a little more at ease then so I asked him," So can I kiss you?" He looked at me and said " Yes I would like that." I moved next to him and leaned in and gave him a light kiss. He was stiff at first but the longer the kiss went on the looser he became. I placed my hand on his shoulder and around his neck. I placed my hand on the back of his head and kissed him deep as I pulled him closer. He moaned into my mouth as he kissed me harder. I broke the kiss after a few seconds and looked at him. I asked him, " That was nice did you like that kiss? " He smiled and said "Yes very much" He leaned in and kissed me this time. We kisses more and I started to run my hand over his body. I started on his arm then moved to his chest. I caressed his chest then moved down and placed my hand on his crotch. He moaned into my mouth as I rubbed his dick. I broke the kiss and said " Maybe we should move this into the bedroom" He smiled and said "Yes I want that" We got up and walked into my bedroom. I had gotten things ready for our date before he came so I had a bottle of lube and condoms on the night stand ready for us. I asked him " Are you clean and DDF?" He said "Yes" I kissed him again and started to pull his shirt over his head. I got it up and exposed his chest. He had a good body and his nipples were hard. I took his shirt off and kissed down his body to those hard nipples. I licked one making him moan then I took it into my mouth and sucked on it. He said" That feels so good" I kept licking and sucking on his nipples as I worked on getting his pants open. Once I had his pants open I broke off his nipples and pushed his pants down and he kicked them off his feet. I stood back and looked at the bulge in his underwear. It looked huge and I could not wait to see for sure. I reached for his underwear and he stopped me. He said "I want to take your clothes off too" So he took my shirt of kissing my chest then my pants. Once we both were wearing just our underwear we stood and looked at each other. He smiled and asked me " What do we do now " I told him to lay on the bed and I laid beside him. I reached over and pulled him over and we kissed again.
As I kissed him I caressed his body telling him he looked so good I hoped he was enjoying it so far. He replied" I have liked everything up till now very much" I asked what he wanted to do next and he said " Let me show you" He then reached over and caressed my chest moving down to my dick. He reached it and placed his hand on my semi hard dick. He said " I have never touched another mans dick before. The only dick I have touched is my own." I said " So how does it feel?" He smiled and said "It feel warm and kind of hard" I told him "It will get harder you know lol" He smiled and said " I know I want that". I reached over and placed my hand on his dick inside his shorts and I knew I needed to feel that beautiful dick in my hand now. I pulled his shorts down and helped him take them off. I told him to lay on his back and let me show him how it feels to have a man pleasure your dick. I took his dick in my hand and his dick felt so nice I asked him " How big doe it get?" He smiled and said "10 do you like it?" I told him " Yes very much" I started to stroke his dick and it started to grow in my hand. I bent down and kissed the tip of it. He moaned and said " I like that" I licked his dick from top to bottom then back up again. I watched it grow bigger and harder. I took it into my mouth and sucked it into my mouth. I ran my tongue over the tip and tasted his pre cum. It was sweet and I wanted more. I sucked on his dick for a few min feeling it grow even bigger. It was making my mouth water it was so nice. I sucked his dick for several mins stroking what I could not into my mouth. I took him deep into my throat and he moaned. He looked at me and said " not even my ex wife could do that" which made me proud. I sucked him more then started to play with his balls. I took each one into my hand and rolled it around in my hand. He had nice big balls and I wanted to empty them so bad. I switched between his dick and balls sucking on each a little at a time making him moan more. I could tell he was getting close to coming so I wet a finger and I placed it at his ass hole. I moved it around his tight brown hole and then pushed it in slowly. He groaned as it went in so I went slow. It took me a little to get my finger into his ass because he was so tight. Once I got it in I started to fuck his ass with it. He groaned and said he was close. So I took his cock back into my mouth and sucked on it hard as I finger fucked his tight ass. I then pushed on his prostate and he came. His sweet cum shot into my mouth once then another then another. I knew his balls were full but I think he came about 2 min. He shot about 4 or 5 shots of cum into my mouth. I drank down every drop. His whole body shook as he came and it took him several mins to come down from his orgasm. Once he did he looked at me and said "WOW that was the best blow job I have ever had" I smiled and said" Thanks I really enjoyed it you came a lot" He says " It has been a while sorry" I said " Don't be sorry I love a guy who comes a lot" I still had his dick in my hand and to my surprise it was still some what hard. I looked at it and asked "Does it go soft or do you just like me? " He smiled and said " I told you it has been a while lol"
I moved up and laid beside him still holding his dick. I just could not let it go it felt so good. He looked at me and surprised me by kissing me. I kissed him back and I felt his tongue reach into my mouth. He said " I can taste my cum in your mouth. It taste pretty good. Does yours taste as good?" I said " There's only one way for you to find out" He smiled and said" I want to do it and make you feel as good as you made me" He then kissed me again and placed his hand on my dick. He stroked it as he kissed down my body making it grow in his hand. He got to it and he kissed it then said " You have a beautiful dick too" " Thanks" I said and he then he asked me " What do I do?" I told him just do what feels right to you. He looked at my dick and then licked it from top to bottom. He smiled and took it into his mouth and moaned. I watched him start to suck my dick and it started to grow in his mouth. He did a good job and it wasnt long before he had me close to cumming myself. I told him " I going to cum if you want you can take it out of your mouth and just jerk me off" He looked at me with a kind of hurt look and took my dick out of his mouth and said " I want to taste your cum too I love the feel of your dick in my mouth. It feels like it belongs there and I so want you to cum in my mouth." I said " Ok just keep sucking me baby and you will get my cum in your sexy mouth." He smiled and took my dick back into his mouth and sucked on me until I came hard filling his mouth. He tried to drink it all but some leaked out down my dick. He drank my cum then licked up what came out too. He smiled and looked at me and said " That tasted great I do not know why I didn't do this sooner." I said "Your not thinking we are done yet are you baby?" " There's more?" he asked. I said yes if you want more. He smiled and said "Yes I want everything I want to know it all" I kissed him and got up. I walked out of the room and came back in with a bottle of water for him and I. We sat in bed naked and talk more about other things. After a while I took his water and set it on the stand then kissed him again. I asked him if he was ready for more? He looked at me and said "Yes please" I kissed him and started to caress his body talking to him the whole time telling him how good he looked and how much I wanted him. I reached his dick and started to stroke it. He started to get hard again and I laid down and sucked on his dick. He laid there and moaned as I sucked his dick. I asked him to get on his hands and knees. He got up and I came around and started to caress his ass. It was tight and hard and I loved touching it. I caressed his ass spreading his cheeks. I bent down and started to lick his ass.
He moaned and asked why was I doing that? I told him " Because I want to give you all the pleasure I can baby plus get your tight ass ready for my dick. I want to fuck your ass baby" He looked back at me and said " Ok but please be careful" I licked his ass hole and started to push my dick into his ass. He moaned and told me how good it felt. Then I wet a finger and pushed it into his ass making him moan more. Once I had him a little lose I put another finger in really making him moan. I kept fingering his ass as I moved around and pushed my dick into his face. I told him " Suck my dick and make me hard so I can fuck your tight ass baby" He took my dick in his mouth and started to suck my dick. He was getting pretty good and had me hard in just a couple mins. Once he had me hard I pulled out and grabbed the lube. I put some on my dick and his ass then placed my dick at his ass. I could tell he was nervous so I took it slow. I placed my dick at his ass and pushed a little. He moaned as my dick started to go into his ass. It was tight as I said but I kept going and after a few min I got my dick deep in his ass. He was moaning and I asked him " Do you want me to stop?" He yelled " NO you better not stop" So I pulled my dick almost out of his tight ass then shoved it back in hard. He cried out but I could tell it was in pleasure not pain. I started to fuck his ass slowly but got harder. I was shoving my dick deep into his ass as he moaned " It feels soooo goood please don't stop" I fucked him hard and I could feel the cum building up in my balls getting ready to paint the inside of his tight ass. I fucked him hard then shoved my dick deep in his ass and came hard. I filled his tight ass with my cream and he cried. Late he told me they were tears of joy it felt so good. Once my dick was soft again I pulled out and laid beside him. He kissed me and thanked me for a great fuck. I asked him " Do you think you may want to do this again with another?" He said " Yes I want to do it again and again but right now just with you" I smiled and said "that sounds great with me baby. Did you cum when I was fucking your ass?" He said " No but I sure leaked a lot the bed is wet where I was kneeling" I said "well I can't let you go without cumming so lay back and let me suck that beautiful dick of yours again baby" He laid back and I took his dick in my mouth and sucked him tasting his pre cum all over his dick. It tasted so good I kept licking it. It grew in my hand so I took it into my mouth and sucked him deep into my mouth. I loved the feel of a dick growing in my mouth and his big dick felt great. I sucked his dick hard as I stroked it and he came hard soon after I started. I again drank every drop and looked at him. He said "I will let you suck my dick and fuck my ass when ever you want just say when" I smiled and said " I was going to say just about the same thing to you baby? I am so happy you had a good time today" He said " I really did and I am so glad I let you be my first I know now that I like sex with men and want it more." Well he and I continued our affair for about 3 years until he found another guy and fell in love. We are still friends to this day. So if you have never been with another guy but have thought you want to be then do not wait go for it and I hope you find someone that will make your first time just as good. Please feel free to leave comments I like to hear how good or bad I did.

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I’m not sure where my interest came from. I think it has something to do with finding my dad’s porn collection when I was younger. I remember one day I was watching this girl suck this beautiful cock on tape. All of a sudden I became so curious as to what a cock in my mouth would feel like. I didn’t find it dirty (well, not in a negative way) or disgusting. From then on, whenever I watched porn, I couldn’t keep my eyes off the cocks. It just became my infatuation. All I could think about was...

1 year ago
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First Timer

I have always been curious about watching another man with my wife!! I finally got the opportunity and it was exactly what I expected. I was a little curious at the time, but I finally got my wife to go to a local swingers club. My wife prepared to go out that evening and she put on the tightest jeans that I had ever seen in my life. Her camel toe was smiling large through the jeans. I almost shot my load just looking at it that alone watching another man enjoy my wife. We got to the club and...

Erotic Fiction
1 year ago
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Teaching a Professor

Ense??ndole a un Profesor Teaching a ProfessorChapter 1: The Course?That way, opposite sexes generate attraction between them. It is an enjoyable feeling that nature imposes us to instigate our instinct of procreation. Having intercourse is in its own a very pleasurable moment for both sexes, just because of the same reason, it is a feeling natures uses to encourage reproduction.?Scott Kendall, 33 years old and Licensed in Sex Education, gave this course year after year, and it was finishing ...

2 years ago
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Teaching Sally The Final Lesson

Teaching Sally, the final LessonIf you read my previous 2 stories. You will remember that as a high school teacher who has suffered through being teased by the young hotties in my class I was frustrated but I never came on to any of my students. However, a former student, a recent graduate, named Sally approached me and confessed her crush on me and how she wanted me to teach her all about sex before she went off to college. And we met and had an incredible “lesson” with me showing how...

3 years ago
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Teaching SisterInLaw 8211 Part II

Hi Readers. My name is Arvind and this is the sequel to my first story on ISS.Thank you for all the positive responses which encourage me to write more of my experiences.This a continuation of the first part- Teaching Sister in LawI had to visit my in laws place again in 6 months’ time after the incident I narrated in the first episode.My in laws were very happy as their younger daughter Rupa was pregnant now and they were thrilled about the news. I reached on a Friday and planned to stay for...

Incest
1 year ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Four Daisy Training Prepares Her for the Workshop

Teaching the Sissy Maid Workshop at the MVP, Chapter Four: Daisy Training Prepares Her for the Workshop Synopsis: Flashing between Daisy's training before the seminar and the seminar's beginning, more is learned about how Daisy trained to be ready as Ms. Rebecca's sissy maid example and how the Sissy Maid Workshop is run to insure the transformation of the submissive male candidates into the sissy maids and cuckolds wanted by their owners. I loved the look on Daisy's face as...

4 years ago
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Teaching Me Part 2

Introduction: The summers fun continues… Teaching Me Part 2: The next day I dont remember getting up off of Kay, or putting my clothes back on, or going to my room and tucking myself in, so I can only suppose Kay did those things for me. I lay on my back in bed, blinking in the strengthening sunlight, remembering the last 2 days, which had flown past, lightspeed. I remembered my first, then second encounter with Doe, and then my little cuddle session with Kay. I remembered how firm and pert...

2 years ago
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Teaching New Position To Young Married Neighbor

We were recently married and lived in an apartment in a big city. Those were the fun days when we were very excited about sex and used to experiment a lot. We had a couple moved in our neighborhood, who were also recently married. Neighborhood lady Mira was in her early 20s, and my wife soon became friends with her. Mira was good looking, with nice figure and her boobs seem to be in good shape from what I could make out from above the dress. They used to talk a lot while I was gone for work.One...

3 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter One

Teaching the Sissy Maid Workshop at the MVP, Chapter One by Scott James Rebecca James is a successful proponent of female supremacy and believes the vast majority of males should subservient and submissive under the control of the woman who owns them. As she does twice a year, Rebecca is preparing to teach a workshop for other female supremacists who wish to transform their submissive male into a sissy maid and servant. I simply loved teaching the introductory Sissy Slave...

1 year ago
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Teaching Susan

Teaching SusanChristine awoke slowly, her head pounding. Slowly she opened her eyes and her senses began to come into focus. As consciousness returned to her she began to take stock of her situation. She is strapped naked to a ridged metal chair her head is strapped tightly across her four head to the chair, a large ball is stuffed into her mouth and strapped around her head.        Her torso is also strapped across her shoulders and below her breasts crossing over her arms just above the...

4 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

4 years ago
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Teaching her a Lesson2

Teaching Her A Lesson The girl next door may be every boy’s dream but the girl that lives next door to me is a monster. She thinks that my backyard belongs to her and that she has free access to walk through my flowerbed and stomp on anything that she wishes too. Tina Louise Carter or TLC as she likes to refer to herself. Tender Loving Care is not what I would to do to her bare ass. At fourteen she thinks she knows it all and that her shit don’t stink. The boys are all over that....

1 year ago
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Teaching her a Lesson1

Teaching Her A Lesson The girl next door may be every boy’s dream but the girl that lives next door to me is a monster. She thinks that my backyard belongs to her and that she has free access to walk through my flowerbed and stomp on anything that she wishes too. Tina Louise Carter or TLC as she likes to refer to herself. Tender Loving Care is not what I would to do to her bare ass. At fourteen she thinks she knows it all and that her shit don’t stink. The boys are all over that....

3 years ago
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Teaching Carol Ch 8

Teaching Carol, Ch. 8 By Zen Mackie When Carol told me that she was going to have to make a presentation on Parent’s Night at her school I knew I’d have to do something to make it memorable for her. I didn’t tell her I was planning to attend; I simply arrived at her room about half an hour before the meeting was supposed to begin. She answered my knock on the door in a dress of dark maroon silk—or some fabric that looked like silk. It was very conservative in cut and came down past her knees....

BDSM
3 years ago
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Teaching Teacher

TEACHING TEACHER By Ashtree The following is a work of fiction/fantasy. It is not intended to condoneor encourage forced sexual acts between females. All character and events arefictitious. Hello, Jenny here again with another story of how much I love raping otherwomen. Remember how my first conquest had been Angela, my neighbour, when Iwas only 16. Well, for days afterwards I'd been terrified that she'd go tothe Police, (this was before I realized how shameful being raped by anotherwoman...

3 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Two Jaimes Training as a Sissy Maid Begins

Teaching the Sissy Maid Workshop at the MVP, Chapter Two Jaime Learns About Life as a Sissy Maid I led Jaime from the garage to my master bedroom in the back of the house and told him to get in the Waiting Position as he had done before and to remain silent until he was told he could talk. I smiled when he nodded his head up and down for yes since he had just been denied the right of speech. Perhaps he may just become as valuable as he appears on first glance, but that was rarely...

3 years ago
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Teaching the Teacher

"Umm, hey, Mr. B." I heard a voice say as my class was leaving.  My thoughts were on two important things.  First, I desperately needed to go to the faculty restroom and second, it was finally lunchtime!"What's up?" I asked, looking up at one of my favorite students at the Community College where I taught.  Her name was Emily and she was a delight to be around.  We'd known each other for years.  I had actually taught her World History back when I was still teaching high school.  She was clever,...

Taboo
1 year ago
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Teaching Shannon a LessonChapter 1

When I met Shannon Brien I was twenty-three, had just gotten my M.S., and was teaching in a community college while I worked on my Ph.D. Shannon was in a College Algebra class I taught in my first Spring semester, and I noticed her as soon as I entered the room. I had broken up with my graduate- school girlfriend some time earlier, so I was very vulnerable to Shannon's very obvious charms; so vulnerable, in fact, that my cock actually stiffened slightly when I saw her in the front row. She...

3 years ago
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Curious 1st Timer

“Ok sexy, see you when you get here.” I’d been emailing “BlackStallion281” since 7pm. I’d always been curious about what it would be like to be with a man. Since high school, I’ve read and seen erotic material about gay sex on the internet. It always gave me a hard on. But this was it, I’m 21 and a man and I can do whatever I want. We’d been emailing each other after I found him on Craigslist. He seemed like a nice guy. Much older, which was ok with me. He was willing to “show me the...

3 years ago
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Curious 1st Timer

I didn’t know what I was getting myself into. I stared at my laptop for a few minutes, contemplating whether I was actually going to be doing this. The email on my screen read:“Ok sexy, see you when you get here.”I’d been emailing “BlackStallion281” since 7pm. I’d always been curious about what it would be like to be with a man. Since high school, I’ve read and seen erotic material about gay sex on the internet. It always gave me a hard on. But this was it, I’m 21 and a man and I can do...

2 years ago
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Teaching Kurt and Dani

Sometimes, people have no idea what they are doing.That was a truth that Monica knew well, though she had no idea it was about to hit so close to home as she drove her Lexus up the driveway to her spacious residence. The divorce from her husband five years ago, after a rocky f******n years of marriage, had left her with a nice settlement and a beautiful daughter. She had gone from having no skills in the workforce to a near-six-figure income during those five years. At the same time, her...

1 year ago
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Teaching Sara Miller

I turned forty five today and decided to write my life story or at least a chapter of my life. I called it “The Unleashing of Sara Miller”. It was all about what happened at a point in my life that caused my life to quickly spiral downward and take a turn to a place no one had expected. I got caught up in a life that I thought I had left behind well before I met my husband of twenty fife years, David. I had suppressed so much of that part of my life that it all exploded and resurrected itself...

Erotic
4 years ago
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Teaching Amanda Chapte two

Introduction: Amanda becomes Grahams real slut Teaching Amanda- Two This story follows on after Amandas first night with her college art teacher, Graham. It starts on the following day, her project/exam day. ***** I felt a cool breeze pass over my naked breasts and cursed myself for leaving the bedroom widow open. My nipples grew hard as the breeze caressed my skin, the smooth feel of the sheets on my naked body aroused me. Then I remembered why I was naked and I smiled, sitting up in bed. ...

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