Many decades ago I enjoyed spending my free time hitchhiking all over the east coast. Pennsylvania, Virginia and North Carolina were my favorite states to drift around. All three are beautiful to travel through, the local food was always good and the people I met were very friendly.
One Saturday afternoon when hitchhiking through Virginia I was offered a ride by an average looking guy that I guessed to be in his about fifteen years older than me (I was twenty-one at the time). You can't be too careful when accepting a ride from a stranger but he was neatly dressed, clean and when he spoke, sounded to be well educated so I hopped in his car.
We made small talk about the weather and news and stuff I don't remember but soon ran out of normal topics to discuss. As is almost always the case with young men, the conversation turned sex. I thought talking to an older man about sex would be interesting and educational because I was eager for him to share his experiences. Boy did I get a lesson.
He asked if I had ever been totally naked while getting a blow job. I only ever had one blow job and it happened in a car at the drive-in theater. Needless to say, I was dressed at the time, just unzipped so I answered no.
He asked if the person that gave me the bj was a guy or a girl. I thought it was a stupid question, the idea of getting a bj from a guy was something I never contemplated so I quickly responded by saying it was a girl.
He asked if I would ever consider getting a bj from a guy and while asking, his hand accidently brushed against the side of my leg. It only took a second for me to realize where this was going and I was about to say no when I realized my cock was starting to get hard. It had been a while since I last had any sex and I was really horny so I responded by saying that I would consider it.
Then the big question came - he asked if I would let him be the first guy to give me a bj. Now I was hard as a rock and I eagerly said yes.
With that, we exited the highway we were on and within five minutes pulled into his driveway. I guessed that he really knew what he was doing because the timing was perfect.
All of the lights were off in his house when we entered, a night light was on in the back of the room and provided sufficient light for us to make our way to an enclosed staircase. We entered the staircase and he closed the door behind us.
The light in the staircase was bright enough for us to see everything clearly. When he saw the bulge in my pants he knew I was rewady. He asked if I wanted to simply drop my pants or remove them altogether. The thought of being naked was so exciting to me that I opted to remove my shirt, pants and shorts. He was tickled to death at the sight of me being naked an asked me if it was alright for him to be naked too. I smiled and told him that I was fine with it.
He undressed, sat on the steps directly in front of me and inspected my cock. When he liked what he saw, he licked the tip, then the head and then took my entire six inches into his mouth. I was in heaven. He told me that it was okay if I wanted to pump into his mouth, he said to pretend that I was fucking a pussy. To be honest, I never felt a pussy that felt as good as his mouth.
As he was sucking me, he began to play with my butt. He ran his finger around the edge of it a couple of times then gently poked it in the middle. I guess I jumped when he did that because he asked if I was okay with what he was doing. I told him that it felt great and to not stop what he was doing.
He slowly wiggled a finger into my butt and worked it around, sliding it in and out and stretching it. With this, I unexpectedly shot an enormous load into him mouth causing him to gag until he could swallow all of it.
One would think that after a first rate blow job, my hard-on would soften but it didn't and he continued to suck it.
Still hard and still getting sucked, he inserted a second finger in my ass and worked it more vigorously. The sucking felt great but what he was doing to my ass was totally wonderful and I didn't want him to stop.
He asked if I wanted to experience an unbelievable feeling in my ass, better than his fingers and more satisfying and I eagerly agreed.
With that, he had me kneel on the steps and bend over while he positioned himself behind me. I knew what was coming.
He told me that I was going to feel some pain for a minute or so but that it would be replaced by pleasure like I have never felt before. I told him that I was okay with a little pain if he wasn't kidding about the pleasure. He wasn't kidding about both.
He slowly inserted the tip of his cock into my ass being as careful as possible. The initial pain pinched and burned and hurt but only for a minute or so. As the pain eased it was replaced by pleasure. He gently worked his cock in and out, each time going a little deeper until he was totally in. His pubic hairs rubbed against my ass each time he pushed in and his skin ground against mine.
He fucked my like that for several minutes and I could feel myself getting ready to cum again. When I told him that I was going to cum he told that he was cumming too. As I shot the largest load I have ever produced all over the steps, he shot an enormous load in me. Geez, what a feeling!
I stayed with him for the rest of the weekend and felt him inside me two more times. Each time lasted longer and was better than the previous.
I say him again a couple of weeks later for a repeat. The last time he fucked me he lasted over twenty minutes before he came. Ask me if I was sore. I have been bi ever since.
What a great time!
13 comments
I have had quite a few of those and I loved each one
I would have sex with that person and have had sex in those situations
Very hot sounds like very hot sex so how did feel the first time very hot. Some real pictures of your ass and cock would be hot, no internet pictures.
I felt a little sore but also felt like something inside of me was set free. I loved it and still enjoy having someone bang my butt. I also felt a little guilty. That feeling repeated itself every time I had anal sex for several years.
Even if he didn't look good. I'm ok with a bit of fun from anyone
I am too.
I have, but sadly decades ago.
That's really nice! Wish you were closer.
This reminds me of way back when I was hitchhiking home from college some weekends. I was 17 and super naive, I was so naive that they could have put my picture along side the word in the dictionary. While I did encounter some different people no one ever hit on me, at least that I realized!! But it was some of the best times in my life and I enjoyed them. I have no idea where I got the courage to do that as I was always starting out after 9 pm. A lot of the people were super cool and interesting, very decent people. Shame Readers Digest ruined that mode of travel. I often picked up hitchhikers in the following years and never encountered any one creepy, just interesting people.
Actually, I was in the Army at the time, I was a paratrooper stationed at Ft. Bragg, N.C.. I never hitchhiked in uniform but also never worried about anybody being creepy. Deep down inside I think I always wanted something like that to happen. That's probably why I enjoyed it so much.
@northmman1053 Shame our paths never crossed
@Terracamo814 It's never too late.
@northmman1053 True
@northmman1053 Where are you at??
@Terracamo814 I'm a couple of miles north/east of Coudersport in the hills.
@northmman1053 Oh wow, that’s really cool, someone that is actually close to actually meet!!
@Terracamo814 I'm about two hours from DuBois.
@northmman1053 mmmm, I want to meet you, how can we make this happen?? Is there a more private way we can communicate to arrange meeting??
@Terracamo814 I would like to meet too. I typically use hunting or fishing as my excuses to get out of the house. This limits my meeting time to daytime and on decent days. I can get away on any day as long as it's during hunting or fishing season. Trout just opened last week and turkey opens in the beginning of May.
@northmman1053 Mmmmmmmmm, I promise to leave you with enough strength to get home
@Terracamo814 Not too much, I hope.
@northmman1053 Just enough, barely. Need to get you home and enough energy for a brief chat with the Mrs so you can tell her you’re going to bed and will chat tomorrow, lol
@Terracamo814 LOL, that works fine for me. What are you planning to do to me that will drain all of my strength? I'm asking because I want to make sure I'm prepared.
@northmman1053 I’m gonna intimately know your naked body, my tongue and lips exploring you and when I find the special places I will shower them with attention to make you moan, squirm and grind as waves of excitement surge through your body, your penis getting harder and harder till it finally explodes
I might suck his cock, or him mine
good story enjoyed first time
Thanks, I appreciate your comment.
A very hot sexy cock
@97Breakout I was thinking the same thing.
Fuckinh hot as hell i want this
Come to Pa and I'll show you one of the nicest asses you have ever played with.
I look for casual encounters and am stimulated greatly when another person shows a great deal of interest.
I'm with you. I think casual encounters are the most exciting. I've had two and both were outstanding.
Now that is a hot cock.
I'm greatly interested.
@OldJoe1010 That's a really nice looking handful you are holding. I wish I was there or you were here, I would love to hold it for you and if you let me, I would do more.
@northmman1053 I'd let you do anything you want.
You have such a beautiful cock head would love to swirl my tongue around it
@OldJoe1010 Beautiful cock. I would love that load filling my mouth. Then I would bend over to feel it deep in my tight ass.
@ready4this42 I'd love getting sucked off, but then you'd have to bend me over and fuck me in my accommodating ass.
He didn't look all that good
he looked great from the neck down.
Why not, hugs Gene.
Yup, that's what I thought.