I had survived two marriages and was looking for the character flaws or physical short cumming s that caused them both to fail. I started to realize I had never in my life, managed to maintain a long term relationship. My first wife liked sex, but not with me. Wife number two didn't like sex or me. Neither was a winning situation.
My quest became both a physical and mental transformation and re-education. The physical was the easier to accomplish. Loosing twenty five pounds and firming up what muscle is there was accomplished in less than three months. A half dozen trips to the tanning parlor tops it off nicely. Dental work is a matter of spending a little money. Taking an average size penis ( about 6 inches) and having it increased to eight and a half inches with an increased circumference was not only expensive but a painful and arduous proposition. Not only do you have to endure the discomfort of surgery but the pain of wearing weights hanging form your cock (to keep it straight) for as long each day as you can stand for several months. Then you are on to using a vacuum pump daily for 10 to 15 minutes for what I would guess is the rest of your life.
I shouldn't complain. The pain, money and effort were well worth it. I might not be what one would call hansom but an average face with the previous additions did improve my desirability and I was still young enough to reap the benefits. I had relationships during the next couple of years and noticed I was becoming a figure of interest among the young women I worked around. Never discount the advantage working for a very large electronics manufacturing company has in providing and unending supply of available pussy. It seems if a person starts making positive changes in their appearance it becomes a topic of general conversation and interest among the opposite sex.
My newest interest (Karen) was a petite blond with short hair, a bubble shaped butt ,pale blue eyes and a face like Charlize Theron. A divorcee with two kids that lived with their father and right from the start was up for most anything sexually. After the eye contact, flirting and required superficial conversations she made a comment about me seeing and experiencing her at work with her little bag of sex tools and devices. She claimed she could drive me to the point of madness. This intrigued me to no end and I couldn't wait for the opportunity. When we did finally get together I was so overwhelmed by her and the sexual feast I was offered I disregardedt her previous statement. This included all the giving and receiving of oral sex I could want. She also included a very detailed and instructive training session in how to please a woman orally. Something I will always be indebted to her for. One of physical characteristics I most loved was though her breasts were small but proportionate to her body she had the longest nipples I had ever encountered. They were normal when first observed but with stimulation grew in length to between a half to three quarters inch long. They were sensitive and with sucking and pinching would bring her to near orgasm in a matter of minutes. This became an area of interest to me so I purchased nipple suction tubes and over a years time the length had increased to between an inch to an inch and a quarter in length making quite a mouthfull. The same devise used on her clit would increase its length dramatic and hold her on the edge of orgasm for hours.
This became part of our foreplay and could make sexual encounters last for hours. After we had become comfortable with each other, she confided in me one evening her desire to be filled up completely. I would not consider her pussy to be overly large and stretched like my second wife’s and my cock size at this time was large enough to cause that extra friction that when you slowly withdraw you can see the pussy lips clinging and stretching as if they won't let go. A vision that drives me wild. It was also apparent she had spent a lot of time developing and strengthening her vagina muscles. She later admitted to doing her household chores with nothing on below the waist with a small weighted dildo that is inserted in to the vagina. It is held in place with the vagina muscles contracted and the weight is increased as the muscles are strengthen. The thought of watching this makes me have wet dreams.
We started by experimenting with different lengths of dildos and found that an English cucumber about 16 inches long and about one and three quarters inch in diameter was perfect in the beginning and when added to a salad later would arouse us both and often start another session. The first time we used a cucumber of this size it took about 30 minutes to insert about ten to twelve inches of it. As I slowly stroked it in and out of her pussy she almost fainted from the pain and pleasure. She was perspiring and groaning as I continued to insert and extract the cucumber almost completely. It seemed as if I could feel it hit bottom and each time it did she would shudder and shake with uncontrolably with pleasure. As she approached orgasm I started to speed up the strokes and got a surprise I had never seen happen before. As the orgasm started she lost complete bladder control and I had pee squirting out all around the cucumber. We were both wet and sloppy but I could tell it was probably the most mind blowing orgasm she had ever had. The sight and sounds of her pleasure had me so hard I felt like the skin on my cock would split.
The orgasm had finally subsided and as I started to remove the cucumber it would start over again. Later Karen said she thought she had three more climaxes after the first one before I had been able to removed the cucumber completely. I had too bring her water afterward before she could talk. Her throat was raw from moaning and she was dehydrated. She told me about wanting to be totally filled up and stretched to the maximum for as long as she could remember but had never before been able to confide in a sex partner to achieved it. The thing was that now that we had gone this far she wanted more, which would keep me entertained finding new ways to fulfill her fantasy.
We were discussing different theories about bring a partner to a more intense orgasm and she mentioned the need for a little pain. I have never been interested in the B&D or S&M side of sex but could see the results of over filling her pussy. She wanted me to allow her to use her previously mentioned little bag of sex tools & devices. I had to agree before hand to let her proceed even if I might not like where it was going. I bargained with her saying I would submit if she would let me attempt to fist fuck her soon. I thought she was going to throw off her cloths and have me start right then. The heavy breathing told me I had just come up with something she wanted very badly. I was amazed she remembered where this conversation had started and she went to her closet and returned with a long makeup bag and a clear plastic bottle. I wrongly assumed it couldn't contain anything that might cause me pain. I was previously thinking of some huge dildo she might shove up my ass or a ten gallon enemy bag. She proceeded to remove my Levis & under shorts. We had been drinking ice tea all afternoon so I started to go and pee before we started. She said it would be better if I didn't. As I layed on the bed she gave me an almost delicate blow job and tied a soft ribbon around my ball sack. Some of the play was to suck me off while using small feathers and cotton swabs to touch and tickle all those delicate places. She then removed a very flexible rubberized rod that was about twelve to fourteen inches long and about a quarter inch thick. It had a rounded end and she applied a lubricant. When she took hold of my cock I could see where this was going and started to protest, but she reminded me that she was willing to submit to the horrid thing I had suggested earlier so I should suck it up. She inserted the flexible rod in the end of my dick and slowly with a lot of burning she managed to get all but a couple of inches in me. I have never experienced an erection this intense in my life. She then kept flicking the exposed rod end and slowly strocked my cock. After several minutes of this exquisite torture she removed it slowly as she slid her hand up and down my cock. I was super turned on but glad this was over. Next she pulled a roll of clear tubing of a smaller diameter out of the bag and with lubricant inserted it also. After insertion she released a device on the end of the tube that had pinched it off. A stream of urine quickly filled the empty bottle. The tube was slowly removed. To my relief she didn't hand me the bottle and demand I drink it. She then removed a long plastic swizzle stick device about the same diameter as the first tube but with a large ball on the end almost twice the size of the tube. We went through the same insertion process as the other tubes but she inserted and extracted this one numerous times very slowly and with the final removal she brought me to climax with a great hand job. This was the first and only time I have ever shot a load of cum that went over my head and hit the wall about five feet above me. For the next two days I didn't think I would be able to ever perform a sex act again. That was my first catheterization and at the time I hoped my last. The inside of my dick was raw and burned for days after.. She later explained that this was something we could not do often for fear of causing infection or damage. I'm scared to death of attempting this again but I can hardly wait for her to suggest it.
A couple of weeks later we were able to spend the weekend at her townhouse. Karen had been trying to get us together since the last session to dutifully fulfill her obligation as she phrased it. I could tell by the way she trembled when we talked about it that the anticipation of being fist fucked had her pussy dripping since I had first mentioned it. I was having doubts as to whether I would be able to fit my hand into her. Even with some of the things we had inserted into her she still had one very tight pussy and with her muscle control she could clench down and almost stop my cock penitration half way through a stroke. She had once clinched and unclenched her pussy with my cock in it for over two minutes with as strong a grip as her hand. She could have gone on but I couldn't take it and had shot my load. Her pussy was the first I had ever encountered that could pucker and kiss me back when I was eating her out.
We started slow with nipple & clit suction and an oral session that brought her to orgasm. Then proceeded to dilate her pussy with ever increasing sized dildos. When I had finally managed to insert the monster dildo ( about two and a half inches across) that was used for window dressing and effect only, she had her third orgasm. I slowly removed the monster after letting it stretch her for awhile and asked if she wanted to continue. She said she had fantasized and masturbated to the thought of a man's hand and arm in her vagina since she had read a story about it at the age of fifteen. She hoped I wouldn't think she was perverse but wanted more than any thing to feel my hand change back and forth into a clinched fist and stroke in and out making her climax until she passed out. I have to admit that I had always wanted to fist fuck a woman but never believed it would happen with someone so small and attractive.
After the dilation process we had just gone through I managed to insert four fingers up to the knuckles without to much discomfort for Karen. Slipping the thumb in took a good 10 minutes more of back and forth pressure but it finally went in past the knuckle also. I was so turned on at this point I don't think she could have got me to stop if she had tried. I could see she was in another world wrapped in ecstasy. I would love to know what is in a woman’s mind at such a vulnerable and invasive time. All I could tell from her sounds, movements and facial expressions was she had reached a level of continuous orgasm and sexual satisfaction no man could ever hope to achieve. I was jealous and would have given anything to experience sex from her viewpoint at that moment. I wound up finishing my self off left handed before removing my right from inside her as I could tell she was beyond giving pleasure for a long time. I don't think she passed out but by the time I had removed the hand that was inserted more than two inches past the wrist she was either asleep or fainted. Later that evening I helped her into the bathtub and bathed her gently from head to foot.
Karen slept for almost 12 hours and was not ready for any sex again for over a week. I was worried she might have regrets and not want to see me again but after our next time together she said she wanted very much to repeat the fist fucking but was going to need several months to heal. Laying together later I told her I had been fantasizing with the idea of having a small horse or very large dog fuck her. After she thought about this for a minute I could see the lust building in her face and her body start to spasm and shake with anticipation. I don't know if I can or will go through with it but I'm sure it won't be long before she will be pressing me to see about setting it up.