Losing My Virginity

I was 19 at the time and had moved to Orlando in the summer of 2011. Went there for school.

By November I had my own place a little studio apartment near the airport. Was my first time living alone. That night I went out and bought the essentials at Walmart. And I bought my first box of condoms! And my first tube of lube! I had never bought those two items before and I figured I was on my own so why not. Definitely was embarrassed to put them on the belt at the check out lol.

Fast forward to a week later and I was checking out Craigslist casual encounters. I would masturbate to guys postings on there. I used to fuck my butt with a sharpie marker as if it was a dick. Three weeks later I found out it was no where near comparable.

One Saturday I decided to switch from boxers back to briefs. Was tired of baggy boxers and to be honest my dick was constantly hard so I needed underwear to hide it. Now I first bought colored FTLs but bought white ones a week later. The white ones played a role in losing my virginity oddly.

It was thanksgiving week. I had the week off from school. Instead of driving all the way back to Ohio I stayed in Florida for the holiday. I had things to put away in my apartment and decided I’d go to a beach one day for the heck of it.

So the day before thanksgiving I decided to go to a beach.. stopped at Walmart to get some swim trunks but couldn’t find any with the mesh liner in them so board shorts and tighty whities it was. I changed into the shorts at my apartment before I went to drive to a beach.

The beach wasn’t too pack but there was definitely people there. I sat out on the beach for 3 hours then walked around some. Had my shirt off the whole time and a guy in his mid 50s started to chat me up. He had a condo near the beach and I mentioned I was from Ohio. Very nice guy. My shorts and underwear were wet from being in the water and I mentioned to him I was going to head to my truck to get my dry clothes then find a public shower and changing room. Then he offered me his shower. I kinda knew where that was going and I looked at him and said okay but I’m a virgin.

He looked at me abs kinda laughed then said I kinda figured. So he walked with me to my truck and he got in and said we can park by his condo. Easy enough. My clothes were on the front passenger seat which now were sitting on his lap. My underwear were on top and he said a tighty whities country boy from Ohio and a virgin. He told me I would be popular in the hookup scene down there.

So parked in front of his condo we got out of my truck. He carried my clothes in. To my surprise he stripped naked as soon as he walked in! He looked at me abs said he didn’t want sand and wet shorts on anymore. Plus he didn’t like to wear them through the house. So I took the hint and dropped my shorts to reveal wet see through tighty whities. Then I took my tighty whities off. He smiled and said your a total virgin.

My dick instantly went hard. His was still soft. It was a decent flaccid size with huge low hanging balls and a nice hairy bush on top. He took me to his bathroom and got a towel out for me to shower. Then he shut the bathroom door. Once finished my clothes were out in his kitchen so I walked out of the bathroom with a towel on. He was sitting on his bed a d he told me I could have a seat while he rinsed off real quick.

As I’m sitting on the bed he comes out of the bathroom naked with lube and a condom in his hand! He sits beside me and tells me to take the towel off. I’m hard as a rock. He doesn’t hesitate. He grabs my dick and stroked it then tells me to lay on the bed. He begins sucking my dick and I cum instantly. He swallows then laughs and said virgins are fun. By this time I’m looking at his hard thick dick. He asks if I want to suck it some and I say yes. So I suck it. He’s precumming like crazy.

Then he gets the lube and tells me he needs to work my hole loose. He started to finger my butt. Boy a finger was a lot to take at first! I was obviously tight. He was telling me a 60 year old took his virginity when he was 22. Told me he was pretty rough too so it’s good I am with a gentle guy. After 20 minutes of fingering me he puts the condom on.

The initial penetration hurt. I couldn’t believe how much it hurt to take a dick. But obviously it was a thick dick going in a virgin tight butthole. He went slow but I still was moaning and groaning. He told me to relax and breathe. Once I’m past that part it will get better. Took about 5 minutes for him to get in and for the pain to stop.

In missionary he fucked me. He fucked me good. He definitely knew how to have sex. He lasted only 5 minutes before he said he was gonna cum. He pulled out. Took the condom off and shot his load all over my stomach and chest! It was a big messy load! As he was coming off the high of his orgasm he said sorry I couldn’t last longer. Your hole was just so tight. I just laughed some

Then I took another shower. This time he was in the shower with me. He used soap for lube and jerked me off in the shower. My second load was just as big as the first and the orgasm was just as intense.

Once showered I dried off and got dressed. Which as I’m standing in my white briefs he commented about my underwear. Saying a tight Ohio country boy in tighty whities is very sexy. He told me once again my ass would be popular in the hookup scene.

Once dressed be told me not to be surprised if my butthole is sore later tonight or especially in the morning. He said it was your first time so you’ll be sore tomorrow morning. Which he was right. I was so sore the next day. He gave me his number and told me if I wanted to go out or talk to call him. He said he’d enjoy another round sometime then told me he’s got a house in Orlando too.

Turns out the guy who popped my cherry was a wealthy guy because I went to his house in Orlando two weeks later to have sex. A house that was like six thousand square foot.