A Seeker's Sexual Pilgrimage Ch. 02

(Author's note: following the break up of my marriage, I went on a sexual rampage through the Internet dating sites. The following are some of the women that I fucked while searching desperately for one I could actually make a deal with.)

*

The first Internet woman I bagged was Maggie. Maggie worked as a medical transcriptionist but after work every day she went to the gym. She claimed she could do fourteen pull-ups.

I went to Lexington one time to visit her and had to sleep on the couch. The next weekend she came to Bloomington. We went out and did the scene. We were in a bar dancing and she started grinding her hips and ass into my crotch. She kept telling me though that she didn't want to get physical. When we went back to my place though I put her in my bed and went to sleep in the study. She kept calling to me.

"Come on, come sleep in here with me."

"If I do that I won't be able to keep my hands off you."

"Sure you can. We'll just cuddle."

I broke down and got in bed with her. He was wearing two piece pajamas, for about five minutes. At one point I asked her to get on top. She jumped on me in a reverse cowgirl. I will never forget the sight of her asshole pumping up and down as she powerfucked my cock.

The next weekend I was supposed to go visit her but she cancelled on me claiming some family thing. After that it came out that she regretted having sex with me and wouldn't see me again. Another born again virgin.

About a week later, on Saint Patrick's Day, I met Sally. Thank God for the Internet. Sally was all wrong for me physically. We met at an Olive Garden in Greenwood. (She lived on the Northwest side of Indy. Later I was to meet half a dozen women that all lived there within a mile of each other.) I was immediately ready to get out of there, but as the meal ended, she said she would like to come see my etchings, a line straight out of the thirties. So she followed me back to Bloomington and we got naked and did it.

A couple of days later I got lonely and called her and we met again in Greenwood and she gave me a blowjob in the car.

So we started to get together regularly. I called her my 'Monday Night Woman.' I wrote a song about it:

My Monday night woman she won't let me sleep
She begs for it deep she won't let me sleep
My Monday night woman she won't let me sleep
Thank God I got a divorce.

My Tuesday night woman gets down on her knees
I make her say please when she's down on her knees
My Tuesday night woman crawls around on her knees
Thank God I got a divorce

On Wednesday night I entertain the twins
Everyone wins when I entertain the twins
They got the smoothest of all of the skins
Thank God I got a divorce

Thursday night I play music with the boys
We drink a lot of beer we make a lot of noise
It's hard to say what I most enjoys
Until I get home and there's Joyce

Friday night I shop around
You never know when a replacement must be found
It may start to sound like I'm kind of a hound
But on Friday night I shop around

Saturday night is orgy night
Everyone gets an invite to orgy night
I got a fistful in my left hand and a juicy right
You just gotta love orgy night

Sunday I save for the best
I know I should be getting some rest
It's be a good idea to be counting sheep
Cause my Monday night woman she won't let me sleep

In spite of the fact that I didn't find her very attractive, we had some great sex. She called herself a 'double breasted mattress thrasher.' She could beat you the death with those boobs. My favorite thing was to get in 69 position with me on top, my face buried in her snatch and my cock deep in her throat. We could fuck like that for two hours at a time only coming up for air.

I started working her asshole with my finger. She had never had that before and it took a while. Like a lot of girls she had the whole 'dirty asshole' thing in her mind. But also like a lot of girls, once she started relaxing and just feeling it, she wanted more.

One night we were down here in my bed. We were in the lazy man position, side by side. I had my dick in her slit and two fingers up her ass. Her ring was getting really loose and she was working my fingers as much as my unit. There was a terrible danger sign here that I missed, she offered me her ass, but she did it because she wanted to please me not to please herself.

"I know what you want."

"What do I want?"

"You want my ass. Go ahead. You can put it in there if you want to."

We paused just like that for a second. I had two fingers up her ass but two fingers were nothing like the size of my erection.

"Are you sure?" I asked.

"Yes, I want you to have it." She squirted me out and moved into doggie position, so I got behind her and admired the view. I doused her with lube, got the pointer in position on the target and pushed.

Sally was terrified actually. She had never been buttfucked and was sure it would hurt. I was no pro. This was my second real piece of ass. The head went in, just the ruby cap. Sally gasped. I pulled the head out and put it back in again. It didn't go any farther than the first time though. She didn't seem to be enjoying it, so I pulled out and worked her up with my fingers some more. After a while the sphincter loosened and I tried my cock again. I surprised her and she didn't have time to tighten up before I slipped in to the hilt in one motion. An ass virgin no more. That tight ring closed on me and I stroked her and watched the in and out and the still amazing sight of my cock in ass and fired my load deep in her. She loved it.

The problem was she started loving me and as much as I loved fucking her ass, pussy and mouth, I didn't love her.

I kept looking around. Early in April I met Dierdre.

Dierdre was the kind of girl who was plain looking. Nothing wrong with her, it was just that her features were all kind of blah. On the other hand as the competition started getting older and falling apart, Dierdre hung in there. Plus she moisturized ever night and had skin like kid leather. Seriously the softest skin I ever touched. Except between her shoulderblades where she couldn't reach. I helped her out there.

She lived in Terre Haute, so after a few emails and a phone call. We agreed to meet halfway at McCormick's Creek State Park. We hiked the trails a bit and I was very polite and courteous. I brought along bottles of water and M and Ms for both of us and that impressed her. I made salmon mousse and salads for our picnic.

After we ate, as it started to get dark, Deb suggested she get a bottle of wine from her car. Sally called while Deb was away. An amazing break until I didn't get off the phone quick enough and Sally heard Deb laughing as she came back and figured out what I was doing on a Saturday night.

Now I'm an artsy kind of guy, in touch with my feminine side although a long way from queer. I've got enough money to take care of me, but not enough to take care of anyone else. I've got all my hair, but I am growing a bit of a potbelly. I like to cook, but I also like to keep it simple. Not really what most women are looking for, but when one that is looking for a man like me finds me, they tend to like me a lot. So when later, I noticed that her body language was wide open to me, I reached over and touched her arm. She jumped into my lap and stuck her tongue down my throat. I slipped my finger down the back of her pants and touched her anus, another score for the assman.

It was a first date and we were sitting on a park bench in a state park, so we contented ourselves with jerking each other off, but it was still quite delightful. Dierdre licked my cum off her fingers. We made a date for next Saturday.

Two days later it was time to see my Monday Night Woman again. Sally had worked herself into a state by the time a got there.

"What was going on when we talked Saturday?"

"I was out with a friend."

"Did you fuck her?"

"No, I did not fuck her."

"Are you going to?"

"I don't know. I'm a bachelor. I can do what I want."

"How do you think that makes me feel?"

"I think I've mostly made you feel real good. Look, I never made you any promises. I even sang you my Monday Night Woman song. What are you freaking out about? Let's make each other feel good."

Astoundingly this bullshit actually worked. Within minutes we were the double ended sucking machine. I guess she wanted my cock so bad that she decided being the Monday night woman was better than being alone seven nights a week. That sounds pretty big headed. I didn't say it because I think I am such a great lover (although recently, two different women both said I was giving them the best sex of their lives) or because my dick is so big (although it is), I said it because I think that was what she actually decided. Now if you ever meet a woman that makes a decision like that, you should cherish her. Get a couple of them going and you have the makings of a happy, contented life, two girlfriends and no wife.

On another level though, it was the beginning of the end with Sally and me because I didn't want two girlfriends (to be fair, I never considered the prospect as a possibility.) I wanted my one true love. That was my quest. Getting laid while I looked was the reality. So even though Dierdre came over to my place on schedule next Saturday and even though we had a nice conversation that went like this:

("I'll take off my shirt if you take off yours."

"Let me think. Okay." And then she let me fuck her doggie style with my thumb up her butt,) it wasn't to last either. This time it was an email from her that she was giving her old boyfriend another chance.

I had a short fling with Patty. She was a skinny piece with no tits or ass. As we sat on her couch on our second date, I noticed that she was having a lot of trouble with her skirt. It kept falling open. Then she would readjust it only to have it fall open again. So I reached over to help her out.

She didn't like to do the 69. "I can give and I can receive, but I can't give and receive at the same time," she said. I'm not really sure why she thought that. I guess it was too intense or something.

Once, I discovered a shoebox that obviously had toys in it. She got all embarrassed and wouldn't let me open it.

After I fucked her doggiestyle one time she told me it was a power trip. Really I just liked the view.

Her daughter was going to college and lived with her to save money. Also, you had to go through Patty's room to get to the back door (no pun intended) and so one time the daughter (whose name I have forgotten) walked in on us while we were pounding away. Instead of excusing herself and leaving, she started asking her mother questions about the groceries and what was going to happen on Saturday.

There I was, frozen on my knees with the tip of my cock inserted in her mother's vagina and the rest of the shaft plainly in Daughter's view. Daughter was staring at it too. "Don't mind me," she said after a minute and sat down on a chair by the door.

Mom had coolly answered the questions about the school event and the mustard and then, as though she had no choice in the matter, had gradually gone back into grinding mode. So after that I thought, "What the hell. Let's give her a show." Showing off was as close as I got to the elusive mother/daughter double, but it was inspiring nonetheless.

I would have definitely gone back for another crack (pun intended) at it if I could have, but the next weekend Patty claimed she was sick and by the weekend after that, I was firmly into a different reality.

First eHarmony hooked me up with a girl in Massachusetts that was pretty interesting. She had started a homeless shelter for women and was making it go fast enough to provide her with a living wage as well as housing several dozen homeless women. That was pretty impressive. Then she set her sights on me and within days had me talked into meeting her halfway at Wheeling West Virginia. She did this by suggesting she was ready to let go of her self-imposed celibacy. She mentioned how much she used to like to wrestle naked and said she couldn't wait to take her shirt off.

At the same time I had just met another woman on Match.com. She was actually that rarest of things, a single Bloomington woman who wasn't gay or obese. We had a really good first date, although not as dramatic as the one I had recently had with Dierdre. So while I was driving to Wheeling to meet Robin, I had a corner of my mind on Cookie. There was little room for Sally and so when she called me, I told her it was over.

She was not too pleased about that and it got a little long distance ugly. This was the first time I had actually had to tell a woman to go away and I was surprised by the intensity of her anger over my rejection. I thought we both understood that we were just having fun.

I've had the anger of rejected women directed at me several times since then. Avoiding that has become increasingly important to me. I think they are being silly a lot of the times. For divorced people to think that something is going to last forever is a little unrealistic. I never promise anything either. But still, sometimes they think I am going to rescue them or that once we fuck they own me and then when I ride off into the sunset they try to shoot me in the back as I leave.

When Robin and I met at wonderful park in Wheeling, she sat me right down and told me her life story. She used to be a big party girl. Then she fell asleep at the wheel and killed an eight-year-old boy. She didn't have to go to prison but she had to do some community service. Then she dedicated her life to the homeless shelter and was attempting to atone. It had also meant no men for quite some time.

I didn't hear much of this. In my mind her voice was still talking about wrestling and getting topless. We went to a motel and got a room. Quickly I had her on the bed. I was straddling her and fondling her tits when she decided to stick with her born again virginity. It took me a while to realize that she meant it and that I had been brought to Wheeling, West Virginia under false pretenses. There's a song about Wheeling, which I did not write.

I cum rolling into Wheeling West Virginia.
My head is high but my heart is still in pain.
My baby said these pills gonna cause me to
Lose faith in ya.
She run off with a wino
I'm gonna drive this truck insane.