Okcupid

Being single I joined a few free dating sites. Had some good dates but had a lot of real bad dates. One date that recently happened was so unique I decided to share.

I was scrolling through pictures when I saw a partial picture and from what I could tell she looked attractive. When I pulled up her profile there was just the one picture showing her from the nose down to her neck. Her profile read that she was not looking for a relationship. Just someone to have fun. She is 38 years old and prefers older men.

So far, so good in my book. I sent her a message reading, "Read your profile and it doesn't say much. Curious what you are looking for. I am an attractive older man. Might be too old for you as I am 62. However, most people think I look to be early 50's to late 40's. Guess I was lucky with good jeans!"

She replied back, "I am a divorced mom of 3 kids. I don't want and don't need a relationship. I am too busy. I just want to meet a man and have him come into my van and fuck me from behind in my pussy or ass or both then leave."

I immediately got excited about this. I have always been curious up anal sex. Tried it a few times but was never able to enter a woman as my girth is to much. Yes, I have measured and it's 6 inches around. Length of 8 /12". Was 9 "not sure what the hell happened to the extra half inch. I am going with age plays a factor.

I replied, "This could be my fantasy come true." I explained to her my interest in anal sex and why it has never happened.

Her reply, "6 inches! I think I can handle that. Send me a picture of you hard so I can confirm."

I replied, "I am a visual person. Send me a picture of your breasts to get me hard."

I get back a picture on her holding up her shirt showing her very nice breasts. They looked firm with erect nipples. I also noticed she had a nice narrow waist. But no face in the picture. This was enough to get the blood flowing and in no time, I was hard and took a few pictures and sent them to her. She replied back. "Very nice."

Over the course of several months we would emailed each other trying to find a time. Logistically was part of the problem as we lived an hour and twenty minutes away. The other problem was timing it when she didn't have her kids. Weekends were out because I coach during the weekends. I started to feel this was never going to happen. During our emails I learned more and more about her. I was able to figure out she worked in HR for a large company near where I used to live. I find out her real name is Ann. Her profile name was Becky. She seemed legit so I continued on with our emails. She even sent me a picture of her putting a toy up her ass and told me it was 6 inches around.

After 5 months of emails one morning I open up my email and see she has sent me an email. "I had a dream about you last night. You fucked my ass and I loved it. I want to do this before I change my mind."

As luck would have it, I was going to be traveling in her area in a few dates. We set up to meet at the Wayside rest just out of town this coming Friday. We were thinking 5 p.m. would work best as it would be dark by then.

As I drove past the Wayside rest on the way to my meeting it occurred to me, I would have to double back to get to it and that would be an extra 15 minutes away. No way would I make it on time.

I sent her an email. "Any chance we can meet in the back-parking lot of Holiday Inn? If you want, I will get a room for us."

Didn't take long before I got an answer. "That will work. Just remember my rules. No kissing. Just sex from behind. Don't need a room. Fucking in my van is part of my fantasy."

It's 4:30 and my meeting is going long. I brought a Viagra pill along because I didn't want to disappoint her incase nervousness keeps me from getting hard. Without drawing attention, I take it from my pocket and fake a little cough covering my hand with my mouth and pop the pill into my mouth.

I see the clock on the wall 4:50. I am feeling warm effects of the pill. Finally, my customer says, "I suppose I should let you go. You have a long drive home."

It's 5:00 when I get into my car. Fortunately, it's only about 5 minutes away. I send Ann an email saying I just left and will be there shortly. She replies right away, "No problem I am parked on the East side of the building. No cars around me."

Okay, I am a man, but always bad with directions. Which way is East. I get to the Holiday Inn and start to drive around the building. I see a grey van as she described sitting by itself. Looks like there is one person in the van. This must be the East side!

I pull up and park next to the van. I see a lovely lady in there and she smiles at me. Then gets out of the van. She comes around the van and I really like what I see. There is no way this cute lady can't find a guy. But who am I to complain? She chose me over the hundreds of emails she got.

"Hello Brian, sorry if I seem nervous. I have never done this before, but I am looking forward to it." As she opened the side door of the van she pointed out the gap between the middle seat and the door. "You could kneel here, and I will get on my knees over the back seat. I meant to bring a pillow for your knees but forgot. I do have a couple of blankets though."

"That should work I." I replied.

We got in and shut the door. "Did you bring condoms?" I pull out 3 condoms of my pocket and show her. "Great, how should we get started?" She asked.

"Well, I need to get hard first." I lied as I was already hard. "Let me play with your boobs a bit." I slid my hands up her shirt and under her bra. They were firm and her nipples were hard. It was hard to tell if she was enjoying it or not. After about a minute she said, "I can see you are hard by the bulge in you pants. I want to see it before you stick it in me."

I undo my belt and pull down my pants and my hard cock pops out. All Ann did was smile.

She watched me as I put a condom on. I told her I probably won't be able to cum as the condom is tight and I have a hard time cumming. I asked her if it was okay to pull out and take the condom off and finish on her ass. She was okay with it.

Ann pulled her pants down and turned around and put herself over the backseat. I guided my cock into her pussy. She was already wet. Probably from the anticipation. I fucked her for about 15 minutes like that. Several times she seemed close to having an orgasm but didn't. She told me to stop for a bit. She reached for her cell phone then handed it to me and told me to record me fucking her. Which I did for a few minutes then turned it off and went back to fucking her wet pussy.

"Play with your clit while I fuck you." She did as I said and played with my balls a bit. In a mater of a few minutes Ann had a nice little orgasm.

I kept pumping her pussy hoping eventually I would cum. Ann looked over her shoulder at me and said, "I think you should fuck my ass now."

I wasn't sure that she wanted to after having an orgasm but was glad she suggested it. I pulled out and lined my cock up with her ass and slowly began to push. I was thinking I would have to go really slow. But in seconds I was deep inside her.

I loved how tight it felt. I slowly fucked her ass. I had to shift positions as my knees were sore and I wanted to get deeper inside her. I moved up and put more weight onto her body. As I got deeper in her it felt even better. I started to fuck her ass harder and faster. The van was shaking pretty good. A quick look around and there was nobody outside to see the van shaking.

"Oh yeah, oh yeah, fuck my ass. You feel amazing. Fuck me hard." She moaned.

"I am close, I think I am going to cum." I said.

"Not yet. I am almost there too." She moaned.

Thinking the tightness of the condom would keep me from completing my orgasm I pounded her hard and fast. She began to shake as she had a loud orgasm saying "Fuuuuuuuck."

This is all I needed to send me over the edge. I buried my cock deep inside her as I felt jet after jet fill the condom. Her ass cheeks squeezed every last drop out of me.

After a bit and catching my breath I pulled out of her. It has been a long time since I have produced so much sperm. I was pretty proud of myself!

Ann thanked me then said, "Next time I will bring a pillow for you."

"Next time? I thought you wanted a one-time thing?" I asked.

"I did. But this was perfect. I can see doing this on a more regular basis. If you are interested?"

"Of course I am." I told her.

We said our goodbyes. Not even as much as a hug. That night I got an email from her. " I forgot to have you record you fucking my ass. Next time I guess."

I can't wait for the next time!