Favorite Masturbation Story?

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I was out walking the dog this morning, in the woods, thinking about sex of course. It reminded me of a time years ago, on the same path late at night, when I stopped and jerked off thinking about one of my coworkers at work, and how she had given me a nice sexy peak of her cleavage while we flirted over lunch. I remember cumming so hard that night, it still remains one of my best solo experiences. What is one of your best masturbating experiences? Was it solo, or did others watch?
 
My very first one. Didn't know what was going to happen then got this stuff pumping out. FUCK!
Oh yes. I was like 9 or 10. Knew it felt good to rub things on my little cock. Didn’t know why. One day was in my parents camper. This later became my masturbation hideout. Laying on the bed and found some course material from a camping chair. Started rubbing it up and down my shaft. Felt really good on the head. Kept going and then it started pulsing and white stuff went everywhere. I thought I peed. But it felt amazing. Did it again later. The rest is history!!
 
In a previous post I talked about the time I was caught masturbating by my best friend. A couple of weeks after that, I had the house for myself and I was very bored, so I texted him to come over.

After hours of small talking and browsing random stuff on the internet, he brought to the conversation what happened between us. I was a little embarrassed at first, but we're very close and he's a very easygoing person, so we just laughed about it. He started to joke around, then he opened a porn site on my PC and browsed through until he found a video within the gangbang category. We were talking about our sexual experiences while watching, one thing lead to another, and we ended pants down, jerking off together.

It was my first time masturbating with someone else, and I love to revive it because it was one of the most intimate experiences I've ever had with a close one.
Please tell us about your other times wanking off pricks. Do you have good sources of vids of helping hands, amateurs preferably?
 
Oh yes. I was like 9 or 10. Knew it felt good to rub things on my little cock. Didn’t know why. One day was in my parents camper. This later became my masturbation hideout. Laying on the bed and found some course material from a camping chair. Started rubbing it up and down my shaft. Felt really good on the head. Kept going and then it started pulsing and white stuff went everywhere. I thought I peed. But it felt amazing. Did it again later. The rest is history!!
Do tell us about your other ejaculatory experiences whether masturbating or fucking or wanking with mates. TIA
 
I had been playing with my little dick for a couple years at least prior to this experience, often taking myself to what I'd call an orgasm, sans semen. I was probably eleven by this time and on this particular day, I was home alone and found, to my delight, a new magazine; one featuring playmates. I undid the button and zipper on my pants, fondling myself as I perused the pictures. I turned a page and there before me was a photo of a young woman with a full frontal view of her body, including a nice bush of pubic hair. It was the first time I'd ever seen what I, at the time, thought was a woman's pussy. So much more to learn! I couldn't leave that page and as I wacked my dick, I was expecting the same old usual sort of ending, but Jesus, it was nothing like that! At the same time my toes curled a white wetness oozed out of my dick. Slippery and wet, my hand found the best way to use it to my advantage. It didn't worry or scare me, in fact, it made my orgasm way WAY more intense than those I'd experienced prior. I don't know if the girl's picture caused me to be super horny, if it was just my time to start ejaculating, or both. It remains one of the most exciting memories I have of that time of sexual discovery. Another would be when the oozing developed into shooting but that will be for another time.
 
In the 90's I had a delightful lover named Diane. We would sit on her sofa and watch porn. She stayed fully clothed and I would get naked and stroke real slow....never coming because we would fuck later and have all kinds of kinky fun. But her taking her eyes off the video now and then to watch me jack off is one of my hottest and favorite memories.
 
I was a late bloomer and 18 the first time I experienced the joy of masturbation. My girlfriend in college was away on a trip. Apparently she obtained some erotic literature and read a story or two about masturbating. I received a call from her that night. She knew I had never masturbated before (Catholic upbringing and guilt). She told me about the stories she read and how she pleasured herself. Then she told me how exciting it would be for her if she heard me masturbate. She guided me, directing me to rub my cock through my pajamas until it was nice and hard. I then pulled out my cock and began stroking as she continued to encourage me. I still remember how damn good it felt. Needless to say, I had a massive orgasm. I came two more times that night. Eventually I masturbated for her as she watched on many occasions. Ever since, I’ve been trying to make up for the lost teenage years of self pleasure 😁
 
I think my favorite maaturbation story was from when I was in tech school in the USAF. I had just bought the December 89 Penthouse and reading Madame Xaviera. A lady was recounting about an older business partner of her husband and how large his cock and balls were. His sexual prowess and the size of his loads. This was my introduction into wife sharing and hot wife's. My cock was so hard that night that it ached. I beat off at least 10 times. I was forever hooked on wife sharing and hot wives! Madame Xaviera, you are the best!
 
I think my favorite maaturbation story was from when I was in tech school in the USAF. I had just bought the December 89 Penthouse and reading Madame Xaviera. A lady was recounting about an older business partner of her husband and how large his cock and balls were. His sexual prowess and the size of his loads. This was my introduction into wife sharing and hot wife's. My cock was so hard that night that it ached. I beat off at least 10 times. I was forever hooked on wife sharing and hot wives! Madame Xaviera, you are the best!
I remember jerking off to Xavier Holander books.....
 
I was a late bloomer and 18 the first time I experienced the joy of masturbation. My girlfriend in college was away on a trip. Apparently she obtained some erotic literature and read a story or two about masturbating. I received a call from her that night. She knew I had never masturbated before (Catholic upbringing and guilt). She told me about the stories she read and how she pleasured herself. Then she told me how exciting it would be for her if she heard me masturbate. She guided me, directing me to rub my cock through my pajamas until it was nice and hard. I then pulled out my cock and began stroking as she continued to encourage me. I still remember how damn good it felt. Needless to say, I had a massive orgasm. I came two more times that night. Eventually I masturbated for her as she watched on many occasions. Ever since, I’ve been trying to make up for the lost teenage years of self pleasure 😁
The first phone sex is very memorable! I was reading AOL chat room conversations, and gave my phone number to a woman. She called me at work, and we had a blast. Fortunately me office was empty for the afternoon, but a few coworkers came back 10 minutes later. My wastebasket was filled with Kleenex.
 
I have had many enjoyable masturbation experiences. One of my favorites was one summer a buddy and I were looking at some Hustler and Playboy Magazines. We were standing there arguing over who had the biggest dick. We both took em out and we wanted to measure. We startled drooping a little. He told me to jack myself to a boner so we could compare. He jerked his hard for me and told me to do the same. He offered to jack me hard and when he reached for my dick I pulled away and started pumping. Once we both got hard he was just a little longer but not as big around as me. After throwing jokes back and forth we each finished ourselves off. i knew that masturbating caused me to cum but I never knew how good it felt until then.

I have had countless fantasy orgasms to related to that story. We pumped each other off, we 69ed, we took each other up the ass. If only.....
 
I always had great masturbation sessions staying out of town. To scared at the time to pay a hooker. Before i discovered CL and DL. I would buy some hot lingerie. Dress up and watch porn. Edge and tease myself exploring every part of my body. Id sometimes have anal beads or my goto which was a vib egg. Id take as much time as i needed, no inhibitions until my body ached. Then finally explode! Shooting my semen all over the room. Then my wife called and asked what i was up to. I just say, nothing much, watching TV.
 
I'm going to bend the rules a little since my most memorable masturbation story was watching an old girlfriend.

In college, my GF was visiting for the weekend. She and other girls in our apartment complex had heard us talk about going to the Campus Theater (inappropriately named since it was across the street from campus and not on it) for Friday night porn movies. It was always packed by drunk (mostly) guys, but girls did occasionally brave the craziness.

Everyone was about ready to go but then one of the girls came running to our apartment to say one of the couples had been in a fight so the girls had to console her and would meet us there.

The guys (about 6-7) went and saved seats for everyone and participated in pre-mobie warm ups (screaming 'taste great' or 'less filling' during oral scenes). Then the Theater got quiet then a low murmur broke out. We looked at the back of the theater and saw our girls prancing in dressed like professional women. They sat is our laps (instead of the seats we saved them) and ran their hands through our hair while kissing us - definitely putting on a show for the crowd. We didn't stay long at all.

Back at our apartment my GF went to my room while I went to the bathroom. When I cam out she had stripped naked and was in my bed furiously fingering herself. I had seen her do it before, but always when I asked her to. This was the first time she did it because she wanted to. Plus. She had left the door open and any could have walked by an seen her. I just watched until she finished then jumped in bed with her.
 
In a previous post I talked about the time I was caught masturbating by my best friend. A couple of weeks after that, I had the house for myself and I was very bored, so I texted him to come over.

After hours of small talking and browsing random stuff on the internet, he brought to the conversation what happened between us. I was a little embarrassed at first, but we're very close and he's a very easygoing person, so we just laughed about it. He started to joke around, then he opened a porn site on my PC and browsed through until he found a video within the gangbang category. We were talking about our sexual experiences while watching, one thing lead to another, and we ended pants down, jerking off together.

It was my first time masturbating with someone else, and I love to revive it because it was one of the most intimate experiences I've ever had with a close one.

Jealous! I wouldn't know which friend to do this with or how to start the conversation. I guess getting caught was the catalyst.
 
When I first came to Lit, I was commuting weekly for work and had time on my hands at night so I started writing stories. I'd get so worked up putting the images into words, I thought I'd split the skin on my cock, it was so hard. It would get so red. I'd force myself to keep writing til I couldn't stand it anymore. A couple times, my first touch would send ropes onto my chest.

The link below to my first 4. Very little, if any plot, but there is a lot of sex in them.

oldbondguy
 
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