Princess loses her virginity [MF]

I had dated Princess for a little over three years, starting a bit after high school. She was a stereotypical country girl, blonde hair, brown eyes, DDs and a Kardashianesque set of ass and hips.

As I had mentioned in previous stories, she had given me head every single day we were together. It didn’t matter where or when, if I took my dick out then she knew what I wanted and would perform without a word need to be said. Several times in a crowded theater, or most often while I was driving. The most memorable time was in her living room while her mom was working on the computer, and all she would have to do was turn her head to see her daughter performing an ungodly act.

After about six months of dating, she told me that she wanted to finally have sex. Since we were both living at home, we decided to go to a motel to do the deed. She said there was no need for condoms since she took birth control to regulate her hormones.

We went to a lousy motel in the middle of the day and spent some time getting warmed up, her giving one of her amazing blowjobs and me going down on her for a very long while, using my fingers to try to open her tight hole as much as possible. When she thought she was ready, she laid on her back and the moment we both were waiting for happened…

Except it didn’t. She was dripping wet (I would later realize that she was a particularly wet girl), and wanted me inside of her like she was in heat, but after trying to slowly work myself into her for 20 minutes, we both gave up. She had managed to take half of my head before her face scrunched up in anguish, and she ended up taking two inches before saying that she couldn’t take anymore. If you saw the pic I had posted in my last story, you’ll see that I’m not a small guy, and her tiny virgin pussy was being stretched beyond its limits.

Over the course of the next two months, we would try at any opportunity we would get. But she was never able to take more than half of my dick, the resistance of her maidenhead was too painful to let me continue past. In every one of these instances, she was in missionary, telling me that she wanted to have her first time be in a dignified position. I made claim to the fact that she had taken half of my dick already so she might not be considered a virgin, but she held fast to the belief that she was a virgin until her hymen was broken.

One night we were hanging out with a friend and his date, and in order to give them some alone time, we decided to take a walk in the neighborhood park. Seeing how abandoned the park was, we sat at a granite picnic table and started making out hot and heavy. Before long I was sucking on her big tits and had my hand up her skirt two fingers deep inside.

She got so worked up that she moaned “I want you to try again”. Knowing exactly what she meant, I didn’t hesitate. I decided that this time I was going to do things my way, and bent her over the table, lifted her skirt and moved her thong to the side as I lined up my dick head to her wanting hole. I coated my dick in her juices and started pushing forward. Her moans and whimpers as I slowly slid inside just made my cock harder, as well as the fact that anyone could decide to walk by at any time. Eventually I was pressed up against her hymen and I wasn’t taking no for an answer this time, putting pressure on it harder and harder until the resistance suddenly gave way.

She gasped in pain and I stopped where I was, holding my place. I asked if she was ok, she told me that she’s in an intense amount of pain but give it a minute to let it pass. So we stood there for a few moments, her bent over a table trying to concentrate the pain away, and me with my dick mostly inside of her.

“Can you stop that?”, she asked me. I didn’t know what she was talking about.

“The pulsing your dick is doing, it hurts”, she responded.

I told her that I was wrapped by a tight virgin vagina, and I haven’t cum that day so I needed some release, I can’t help it. She decided that she couldn’t take it anymore and said that we should stop. As I pulled out of her, she winced and groaned. I didn’t look at the aftermath and we put ourselves away, but we had to walk extra slow back to my car.

As I’m taking her home, I asked if she considered herself a virgin anymore. She said that she thinks that her virginity has been obliterated. I laughed at her choice of words and took her home.

The next day I didn’t have class so I slept in, but she called me up and said she was on her way over for her lunch break. When she arrived, she wasted no time and said she wanted it in her again. Seeing as I had an empty house for only a few moments, I bent her over on the floor and tried to work myself in. To my surprise, she was already wet and good to go. I was able to work myself fully inside with only minimal grunting and pain on her end. I found out that day that when she got dicked, she’s a very loud moaner. An outside noise spooked us, so we stopped.

The next time was when we were up late watching the World Cup. She decided that she wanted to get on top of me while I was sitting on her couch. She took her time working her hips up and down, taking me inch by inch. Before long she was riding me with abandon, and I had to hold her mouth closed because her moaning was loud enough that I thought it would wake her parents. It didn’t take her long until her moans became whimpers as her face went flush as her orgasm hit her. This was the first time I realized that I could make girls cum by just sitting back and letting them ride me until they’re satisfied.

I kept pumping myself into her and my own orgasm soon followed, filling her with raw cum. Her eyes went wide as I shot my jizz into her, and she asked if I came inside of her. I said yes, that it snuck up on me fast (this was actually true as an overly horny teenager, not just a lame excuse). I asked how it felt, she told me it felt foreign.

The next three years would be remembered by the fact that I came inside of her, one hole or another, at least once every 24 hour period. She became rather determined to get fucked anally, but despite all our attempts we never succeeded on that end and eventually we went our separate ways.

A little after we parted ways, we still kept some level of contact. She confided that she had to start doing kegal exercises because her new boyfriend was only average downstairs, and it was difficult for her to get off since she was accustomed to being more filled out. I didn’t reply other than give her a shit eating grin, and she then got angry and told me to forget it.

I’m sure I’ll remember more, and perhaps I’ll add to it. I haven’t spoken to her in years, after Crazy took my phone and told her in not so uncertain that I can’t talk because I was about to get my dick sucked. I still laugh about that when I think back on it.

Source: reddit.com/r/gonewildstories/comments/bf0lf5/princess_loses_her_virginity_mf