Obsession of the Mind Ch. 02

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(Please read chapter one first. This story starts off slow but it will blossom to a total delight for SPH and cuckold fans.)

Continued from Dr. Saza’s office…

“Can’t you prescribe me something that will make it bigger?” I asked.

“Well you can take those pills they advertise on TV, but I’m skeptical that they will give you any noticeable results,” she replied.

“But what about my sex life, how can I find a girl that doesn’t care about the size?” I asked.

“Well you should try to look for a woman that has not had very many previous lovers or even better one that is a virgin. Did your previous partners express any discontent?” Dr. Saza asked.

“Well the only girl I actually penetrated had only had one previous boyfriend. I’ve only had oral sex with a few other girls, but it never went all the way,” I replied.

“I see…”

“I really want to get back together with Rachel, it’s been years, but she never complained the few times we had sex, even though I only lasted a few minutes.”

“There you go, you need to rekindle the romance, she seems not to be interested in penis size,” she replied.

It had been three years since I last saw Rachel. She was a beautiful young woman only 19 when we had met. I truly loved her but, during my addiction to alcohol I managed to ruin that relationship. I do wish I could have her back.

“What are you thinking about?” she asked, breaking the silence.

“You are right. She is the right person for me. I only hope she will take me back,” I replied.


It didn’t take me long to find her in this day and age of social networking sites. She was as beautiful as ever, though I could only see a small picture of her face as her profile was set to private. I made an account and added her as a friend with a short message asking how she has been doing.

It only took a day before she replied. She said she was busy with life in general and was glad to hear from me. I studied her profile for a while focusing primarily on her photos. She had been less modest than I remembered her to be. One picture was titled ‘miss this?’ and it centered on her bubble butt falling out of tiny shorts as she turned to look at the camera. I couldn’t help but wonder why it was labeled as such. You have to have something first in order to miss it later. Am I to assume someone was missing the piece of ass they used to get?

I used to get a piece of it, well I never got anal, I only wished. Was she referring to me? Not likely as we haven’t spoken in years. Of course esat escort she would have had boyfriends after me. What was the likelihood they were larger than me. Very? Is this worth pursuing?

I spent a while pondering so many questions but soon found my self jerking off to the picture. My thoughts were focused on her ass wondering if it had belonged to someone else. I wondered if that someone also had a large cock.

Upon finishing and regaining my composure; I was bold enough and confident enough in light of my new found medication to ask her to see me. To my delight it took only a matter of minutes to read this reply:

***Why after all this time do you finally message me? Have you gotten your life together? I would love to see you again but I don’t want to go through that same shit again. I just got out of a terrible relationship and I need stability in my life. Please don’t message me unless you are serious.***

I was in. The love of my life was back in my life. The butterflies were back and I could hardly wait to have her in my arms again. I messaged her back that I missed the great times we had together and that I was only interested in getting back in touch, not to come storming back into her life. That I would take it slow as she wanted and about how great I had felt lately and how things are coming to order in my life.

***Pick me up tomorrow I would love to whoop your ass at a game of pool for old times sake 😉 972-555-2345***

I decided I would call her tomorrow to finalize the date. In the mean time I prepared my clothes and groomed myself to highest standards. Life was great.

The date started off well. She was an absolute tease from the start. She wore tight fitting, low cut jeans. Her toned stomach was slightly visible when she moved about. Her ass was just amazing in all its glory. She never had large breasts but it wasn’t much of a drawback. She didn’t wear a bra and her nipples were noticeable through the light pink halter top.

We used to play pool in our past, and almost always had a wager on it. I was better but I let her win some so that when the time came around for a large bet she wouldn’t back down. Though, nothing much ever came of it other than exchanging massages or preparing dinner for the other.

After a few games we were tied and she proposed a wager. If she won I would have to pay her phone bill. She asked what I would want.

“How about a blowjob?” I asked.

“That’s all you guys ever think about.” Her face turned long.

“No I was just kidding around. etimesgut escort You know I care so much about you. I have been waiting for this day for so long. I’ve wanted you back in my life so badly.”

She smiled. “Okay, calm down.” She came closer and gave me a hug. Her hair smelled so nice. She pressed her chest against mine and I pulled her hips in closer. She whispered, “I don’t want to get hurt again, promise me you will do anything for me.”

“I promise I’ll always keep you happy,” I replied. I took the initiative and kissed her tenderly savoring the moment.

After a few seconds she broke off the kiss and looked me straight in the eye. “So if I lose I give you a blowjob, huh?”

“Sure,” I smiled.

I thought it through while playing the game that I would have to lose in order to obtain a bigger bet in the future. She had a come from behind victory and was full of herself. But I was happy she was happy. I told her I should stop by her place so I could take care of the bill. She playfully rejected. But I reminded her I needed to see the amount to keep the bet honest. She gave in and we left to her place.

We made out three times before we even made it inside her door. I had a good feeling I was going to get lucky. She went to her room and told me she would be right back. When she returned she was wearing the same shorts I remembered seeing in the photo. I couldn’t wait to get a close up view. She sat next to me and it wasn’t long until we were making out and feeling each other up. As I started to remove my pants she asked, “Do you have a condom?”

“No, I can run to the store though,” I replied.

She stood up and grabbed my hand to lead me to her bedroom. I never fucked her without a condom before I was excited I was going to feel her warm pussy around my dick any moment now.

She told me to lie on the bed. I watched her sexy ass fall out of her shorts while she opened her dresser drawer. When she came back she through a condom at me and told me to put in on.

I started to panic I looked at the wrapper and it said magnum; I knew it was for large cocks. She stripped naked and watched as I fumbled with the wrapper. She decided to lend a hand and pulled down my boxers. It was the moment of truth.

To my surprise she didn’t miss a beat and took the condom from me to put it on my throbbing little hard on. It was obvious from the start it was not going to fit. She pulled it down my shaft anyways and just stared blankly for a few moments. The condom was so loose that when she grabbed etlik escort my shaft and stroked me it slid right off.

“This isn’t going to work. I don’t have any smaller condoms.”

My dick was aching at the thought of her being used to big cocks. She had a drawer with oversized condoms for some ex that fucked her with his huge dick.

I tried my best to keep the moment going and pulled the condom down and pinching it at the base with my thumb and forefinger. “I’ll hold it in place,” I said while motioning her to get in position. Her pussy lips had always been one of my favorite of her attributes. They were a bit oversized and when she spread them with her two fingers it drove me wild.

She was almost sitting on me before my short penis had made contact with her prize pussy partly due to her round ass cheeks hanging firmly below her opening. She leaned forward so that more than just my small cockhead would enter her. Her pussy offered very little resistance accommodating my tiny prick. She began to move her body up and down and instantly my penis fell out of her wet cunt. Her disapproval was becoming more and more apparent in her facial expressions. Her dissatisfaction with my undersized dick was putting me on the threshold of a very premature ejaculation.

I panicked as I still, in the back of my head, didn’t want her to end up leaving me so I held her hips and pushed my dick as far as I could inside her. She let out a slight moan but I think it was more because I was rubbing her ass and spreading it as I held her tightly. I felt the heat at my fingertips and so badly wanted to probe my fingers deeper and lower until I felt her tight asshole. It all quickly had become too much for me and I blew my load inside the condom. As I pulled out I noticed I only filled the condom half way as the other half hung there unappreciative of my lacking size.

I could see the disappointment in her eyes. Things were seemingly going great, sparks were flying and it all came crashing down when she discovered my dick was far inferior of what she was accustomed to receiving. I was yet again surprised as she smiled and kissed me and said she had missed me. She began crawling on her knees, still above me and I knew I was about to feast on her pussy for the first time.

It was quite clear she was going to get hers, so to speak. I was happy to oblige and began sucking on her supple lips. She moved her hips slightly back and forth as I presented my stiffened tongue. I made subtle efforts to lick below her pussy. She responded indifferently. After five or so minutes she climaxed as her juices dribbled off of her extended lips.

All in all it was a huge success despite my diminutive size. We cleaned up and cuddled beneath the satin sheets as our soft whispers subsided to heavy eyelids.

To be continued…

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