If you could travel back in time to relive one amazing masturbation session, which would it be?

the time your wife was away and you were home alone?
when you first discovered internet?
when you had your first apartment?

The day I first discovered my dads Mayfair magazine.

I would have to say when the wife was away I actually tried the hallowing out of the cucumber it was a awesome experience need to try it again would highly recommend it

Do they grow cucumbers big in Texas?

Everything is bigger and better in Texas ;-)

I've done it, but it's hard finding a cucumber big enough!

my first time was an absolutely incredible surprise. i was 11 and home alone because i was sick from school. at school everyone was talking about getting sucked off and how great it would be to get sucked off. i really didn't have much of a clue what they were talking about, but thought it must feel good to have your cock sucked on. so i contemplated how i could accomplish this. it so happened that our "electro-lux" was sitting out not far from where i was, so i went over to investigate. i thought well it sucks and it has a hole big enough in the vacuum hose for my penis, maybe i should give this a try. i took off all my clothes and started the machine. i was a little apprehensive at first, but then stuck my small penis in the end of the hose. the metal hose end took hold of my penis and made it stretch and vibrate inside. it didn't feel too bad so i let it continue until my hips started to involuntarily to shake. i pulled the tube off my now convulsing cock and clear fluid was dripping out all over the floor. i was totally freaked out and was fearfully shaking. i thought i had really hurt myself good with this stupid idea. i wiped up the mess and put the vacuum away and kinda felt sick to my stomach for a couple hours and laid on the couch. scared of what had happened that day. about 3 days later i got curious again. i was afraid to tell anyone what i had done and wondered if i tried it again, would i get the same results. so being alone after school i got the vacuum out again. this time i was more prepared and had a wad of tissues nearby. i turned the machine on and stuck my dick in the end of the hose like before. the suction pulled me in and vibrated my cock and i could feel that unusual feeling starting again. just as i was about to go off i pulled the tube off and spewed the clear liquid into the tissues. wow... not too bad i thought and i'm not even afraid this time. my relationship with the electro-lux continued until my cock grew too big for comfort in the metal hose end and i graduated to using my lubricated hand.

prob my first jo with a buddy

I remember being at home alone and deciding that I was going to cum...had never before but tried it....it was amazing....went through bottles of lotion that year

Probably would go back to a night a coule of years ago when our best friends were in our bedroom with us and we were having one of our "parties". It just so happen my wife was having some issues with pain her stomach and was unable to have sex that involved penetration. So as the husband of our friend was eating his wife's pussy I began to eat my wife. After a short period of time he began to fuck his wife awhile I continued to lay on m back eating my wife's pussy. Jill was laying beside me gphead at my feet. Finally she reached up and began to slowly to jack me off. She has these hive tits and I began play games with them as she stroked me and I ate my wife's pussy.perhaps the best part, aside from getting to suck her beautiful large tits and great big nipples in a later session, was the way she stroked me off. She never missed a stroke and as I came she continued to work my shaft until every drop of gov was out. She later said she felt sorry for me that I was the only one who wasn't getting off. I still haven't gotten my ultimate fantasy a threesome with her and my wife but it as pretty close. It keeps my showers a little longer. Later on I did get to finger her and later suck those great tits. But this remains a great memory.

It would have to be in my teenage years. I was in major lust with my best friend's mom. Judy was divorced, in her early 40s, about 5-6, 140 pounds, blonde, tan, nice legs, big tits, big ass. His family went out of town on vacation and asked me to watch the house, so they give me a key to let myself in.

My first stop was right to her bedroom, where I found pairs of her worn stockings and panties in her laundry hamper and pulled out a few pairs of well worn heels from her shoe closet. I also found her vibrator tucked away in her night table.

I lay down in her bed and absolutely inhaled her intimate scent while I stroked my cock for a couple of hours. Can't remember exactly how many loads I blew, but being a teenage boy, I'm sure it was at least five. And I got to do that several times over the course of the week they were gone.

I can still remember the scent of Judy's panties, nylons and shoes ... but I wish I could go back 30 years and do it all over again.

Way back when I was single in my apartment before the internet I'd have these massive masturbation marathons in my living room. I'd go rent 5-6 XXX VHS tapes, set up a lounge chair in front of my tv with plenty of pillows under my butt to elevate my cock and cover everything with towels. I get set up with some cold adult beverages, some nose candy, and lube for my cock. I jack off for hours with a rock hard erection watching the porn and enjoying my dick. There was an occasion where I had a multiple orgasm, learned to edge (tho I didn't know it at the time). Often when I finally came the cum was so hard and intense it would shoot over my head. Now it's all about the laptop and I still love it but can't get into it to that degree at home, only when I travel.