Tale 2 - Hoo Up

Well once I was done with the Origin Story on how I became a Plenty of Fisherman I was set and ready to begin my adventure and a journey of self discovery and enlightenment. It would prove that everything I thought I knew about dating and women was all wrong. I would see things I could only imagine and things quite frankly I could not imagine.

This is the second lady I would meet. Number 2 was someone that had knew some of the same people I did. I was a driver and she dispatched for a different company.

This would be one of my strangest experiences and looking back on it now I still do not understand what happened and will likely never know even as I am getting closer to 50 years old.

Dear Penthouse forums I never thought it would ever happen to me.........

Crap.......... Hope that does not get me a copyright strike. Oh well the joke is likely old as the opening line. I did not think it would happen period. This was the second woman I ever met on POF. I was new to dating and that was the second time meeting someone. I talked to her a while before we met and thought she was sane. Hell that was the purpose of the chat function on the site. I was young and naive back then. And while she appeared sane from the conversations she had some shall I put it delicately hobbies.

She invited me over to her house. I brought a pop with me because I do not drink and I did not want to impose. I had a belt pouch which I kept a lot of useless crap like cough drops, a small pill container with some gravol and aspirin, toothbrush, and condoms. Just because I had something in the pouch did not mean I expected to use them. Never did use the cough drops or toothbrush.

We were talking for a while. Small talk nothing special then things started getting a bit strange. She had a mini lap top. She got a message on it gave a quick reply and sat back down. She said it was a message from a guy that wants to be my master. He wants me to pick someone to have sex with. I said the guy was an idiot. You might be thinking that was probably a hint. You are right but I was young and incredibly innocent then. Lets be fair. It is hard to describe how clueless I was. There was no way I could wrap my head around the idea of that even being something that happened in real life. There was no way I could expect to be in the same room when it happened.

So she gave me a hint or at least given what I now have concluded was a hint. At that point she might have been a bit amused and shocked that I did not notice the hint. Well we started talking some more and she took off her tank top. She did not have a bra. That was a better hint. I could not fuck up that hint. Still I was young back then...........

So I asked May I?

Seriously she whipped her tits out and I was still asking permission but I am polite. It was a bit weird. The girls are out there swinging in the breeze and I am still being polite and not just jumping on the obvious invitation. I lived a very sheltered life and in no way was I prepared for this moment or even able to imagine it happening. Still naked breasts and an open invitation. Nice erect nipples and at that point my penis told my brain to take a break. Send the blood flow down south and he had this. It was not Sophies choice and my brain had no problem sitting back grabbing some popcorn and enjoying the ride while my penis took control of the show from that point on.

She wanted me to bite her nipples. I do not like causing pain so I used my tongue to put more and more pressure on her nipple and when I found the right pressure she started moaning. I was weirded out by that because that had to hurt like hell. She was squirming and getting really wet so she must have liked it a lot. My first lesson is that some women like nipple biting and pain. No matter how strange it is to me I just went with it.

Tip of advice for anyone is pay attention to the reaction of the lady. If you see she is not responding change things up. When you see something she likes then use that happy button like it is the F-Word in a rap song.

That was my second time with a woman and she actually knew this. It was not like it was hard to tell that I was greener then a St Patricks Day parade. Probably why she picked me. I was not quite a virgin but I still had that new car smell of one. When her master ordered her to pick a guy to have sex with I was a nice guy that has not banged 3 digits worth of partners with the STDs to prove it.

After the nipple biting she was very eager to get her pants off and see what I was like behind the drivers wheel. Wish I could remember more but between my brain screaming yay titties and the blood for any memory retention being controlled by my penis. Well I was lucky to even remember basic things. Sorry penis but you are being thrown under the bus here for not leaving my brain enough blood left to remember too many details. Still in the defense of my penis he put on a hell of a performance getting up 4 straight times.

This is about the last thing I remember before my penis started calling the shots. She bent over the bed. As soon as I got the condom on I got behind her. I had my hands on her hips. I was painfully hard. She reached back and lined me up. There was a lot of excitement. After working on her breasts she was ready for a hard pounding. She was making it easy by taking the lead and backing up on to my penis. That first thrust was all on her. She took me inch by inch. Her pussy was gripping me tight and was so hot around my penis. She was driving the length of my penis into her in one motion. Then after I was all the way in her and buried to the hilt I started thrusting in and out. I came hard of course but I stayed hard. After replacing the condom it was time to grab her by the hips and start ramming her doggy style again. And this time I lasted longer and went more smoothly creating a rhythm she liked a lot.

So after 3 condoms she asked me if I wanted to put it in her ass. If I was more experienced I would have known it was because I wore out her pussy. I had a bunch of condoms and would go out and get another 12 pack if needed. Anal is not really my thing though. I would rather stick with the hole that tastes better. Like I said I was new to this. In hindsight I could have gotten laid a 4th time if I was open minded and just shut up. If a woman tells you to put it in her ass and you have condoms do not argue. Just shrug and enjoy it. Hell when I was done with the anal she might have been ready for a 5th time after giving her pussy a breather. And yeah there are guys that go through their lives wanting to have anal sex and I had it offered up on a platter and I passed on it.

Yeah I was an idiot. But be fair here. This was only the second time having sex I was nowhere near ready for Anal. I had no idea how to prepare myself or her. She probably would have guided me through it so I did not hurt myself or her. But then again she seemed to be into pain and me being as green as I was I could have ripped her up bad. I am probably still not ready for Anal but at least I am experienced enough not to pass it up. Still not my preference.

Nothing really too strange here. Heaven knows it is likely by far the tamest story to be posted by anyone. Someone could read this and think it is cute that this is considered strange. To me though this had totally blown up any notions I had on what dating and meeting women and what dating was. If I was told this story before it happened I would have laughed my ass off at how ridiculous it was. Fact is stranger then fiction though.

This is the fucked up part though. It has been over 10 years now and I still have no idea if her master was watching me having sex with his slave on the Lap Top webcam. That was my second time having sex and for all I know there is a sex tape. If there is a sex tape I would love to have it though. It does lead to amusement. I got hit on by a cashier at Walmart. My girlfriend who was with me at the time was not happy about it. When she told me that I was being flirted with I said one word. Really? Yeah she knew the story. I am the guy that missed every hint in the book until a woman takes her top off and the girls start swinging in the breeze. I am not exactly the most observant when it comes to being flirted with.

Despite not having experience this was the second woman I met off POF and I got off 3 straight times. What I lacked in experience I made up for in enthusiasm and an unrelenting hunger for sex.

The thing that makes this truly strange is this is only the second woman I met. To recap. She was the first woman I had sex with when dating. She was the first one to offer me Anal. It was possibly the first and only time I had sex with someones slave. Also the first time I was possibly videotaped. One of my favorite memories.

Kind of a little regret because most guys dream of being offered Anal and I should have at least tried it.