I hope there are other couples who can relate to this story as it's my story of what it can be like dating with an infantile penis. It may sound harsh but now I laugh about it.
I met Kathryn while in college. She was my first girlfriend and I was a virgin before I met her. I was a finance student and she was a 1st year middle school math teacher who, I found out later, was previously married to a black guy. I was generally very timid around women and kinda awkward, but still attractive and ambitious with my studies. Kathryn had a thing for slim fit guys and was drawn to me right from the start after meeting through a mutual friend named Kim who I had met at a social club where we played bridge. She was older but attractive, cute round face with strawberry blonde hair, and a voluptuous figure. She was out going and very forward, which put me at ease. The first time we had sex, we were both very much in love. She had 30 candles lit around her bedroom in the dark which i thought was very romantic and knew it was an invitation to be intimate. This was the moment I had subconsciously dreaded for some time now. I wasn't sure how to move my body and was petrified that my size would be a problem. To make matters worse, I know now that Kathy, although having strong vaginal muscles, was easily aroused and had a very open inviting pussy that was used to a much larger husband ex husband. I took off my clothes in the dark after her and to my relief she did not make a comment, and her facial expressions remained the same before i had undressed, very intent on making love with me. I looked down at her privates rather confused as to how I was going to make it work. She noticed I paused and glanced down at me to see what I was doing and told me softly to go all the way in as deep as I could and then all the way out and back in again. I felt this was going to be a bit of a challenge but feeling a bit humiliated that I was given instructions, I quickly proceeded. I genuinely ended up enjoying my first time and learned that I was not quick to cum, having taken about 30 minutes. She seemed pleased and we kissed the entire night afterwards and are relationship grew stronger. Eventually are sex life fell into a routine. I slipped out quite often during sex, upon which she would say "oppsie" almost as if to embarrass me. Doggy style was impossible for me to even get inside her pussy. When i was finished she would roll over and go to .... I was generally encouraged to have oral sex with her, and she went great lengths to provide me with flavored oral lubricants to choose from. Generally she had the tv on during sex and during jeopardy she actually answered the questions while we were in the act. It unnerved me at first but I got used to it after a while. I started to get hints that Kathy might have been a size queen, most noticeably the show "hung" listed as a favorite on her facebook page. I can still remember the jeopardy question which changed our lives in an instant, in which we both answered the question at the same time. Some how this triggered her and she went into a fit of laughter. I asked her why the laughing and she started to calm down and told me of her ex husband and how large he was. She curled her lips and said he was "like this" and she held her forearm up and made a tight fist. She also has the facial expression like she was impressed by her arm which was really representing his cock. I thought in my mind this was an exaggeration but beyond that I was bewildered why she would be talking about this as if i was her girlfriend. I got angry and explained to her that this was hurtful to me but I thought she was just joking. It may have been a day later that she for the first time examined my penis up close while i was not erect, which all i have is a stubby head poking out. With two fingers she very carefully tugged to lengthen me and my penis was not going any where. Then, with one finger she turned the head side to side looking rather surprised that there was virtually no length to my penis when flaccid. Almost in a gasp she said, "You're so little." I immediated corrected her that I was not erect. She then went on to say that , "No, your're actually very small. You're the smallest I have ever seen." My heart sank but my face remained emotionless like I was in shock at what was happening. I was always a little shy about my penis size before meeting Kathryn but I had no brothers to compare to and was raised by a single mother. Like every guy at one time or another I measured myself when fully erect and I was exactly 3 1/2 inches on the mark, and about 4 inches in circumference. I told her that her ex boyfriend was a freak of nature and that she shouldn't compare us. She then went on to say that she had only dated black men before me and they were all much bigger.
It was maybe a month later we were watching an adult show on HBO documenting exotic male dancers, who were all black and latino. Are hands were already clasped together while I was viewing for the first time, very large men who made my size look infantile. I started to sweat bullets. My hand became clammy and she smiled and looked at me to say, "look I told you so."
It became a reality check for me that she was telling me the truth before and that I wasn't satisfying her at all in bed. I started to ask the obvious questions, like why she was with me or could even put up with me knowing I was small. She always told me she loved me. But one day her love came with a catch.
The cuckolding is an entire story of it's own. If there are any people interested, I would love to tell how we turned made cuckolding work for us long term.
- December 2, 2012 3:20 am
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lovesfun and cumalex like this.
nice story, have some later?
It started out innocently enough with us incorporating toys into vaginal play. She had purchased a purple jelly dong measuring 8 1/2 x 6 1/4. I did not know what reaction I would get from inserting it inside her for the first time but I was rather surprised she took the entire length with ease on the first thrust, and upon doing so, i noticed her head cock backward and her mouth opened wide. A smile quickly grew across her face, as if to say to me, this is what she's been missing. I watched her shutter in orgasm after orgasm, and her cum for the first time in front of me . Increasingly, I was being denied intercourse, not because she enjoyed denying me, but simply because she had lost complete interest in our sex life, saying "it was like watching paint dry."
It took me a while, but eventually I confessed to her a fantasy I had of watching her with her previous well endowed ex. This became a regular conversation of ours and by then we both knew what a cuckold was but it was never discussed until one day she said to me, "I couldn't handle it If you ever cheated on me." I knew she loved me so this was obvious but I told her that I wouldn't ever consider that but it might be ok if she had sex one time with another man who had more to offer her in terms of size. She then surprised me with the fact that she had been corresponding with a well equipped man for quite some time now and that they had regular phone conversations. I told her that maybe we should leave it at that and not take it any further.
Then came the cuckolding. She had told me she was working late after school on a big rainforest preservation project with the middle school kids she was teaching. I expected her home late, what I did not expect was her to be in the mood for sex. Upon entering her I noticed her vagina was gaping open and even more jaw dropping was the fact that I could not touch the sides and she was a oozing a milky white substance that I had seen before with our dildo play, but this time it was creamier. I felt a warm sensation around me as her vagina made its way around me, but much looser than I had ever felt previously. It felt like I was fucking an ocean, and the look of embarrassment on both our faces was priceless. Scared, frightened even, I asked her if she had just used the toy and she smiled and shook her head. She said, "I can't even feel you." I asked her what was going on and she went on to tell me that she took me up on the offer. She had sex with her hung lover. Completely humiliated and mortified, but yet still intrigued, and buzzing with excitement I cam inside her already cum filled pussy. Unable to contain myself, I had to ask her of all the details of her encounter. She told me he was clean but that her sexual encounter with him was going to change things. The new catch of our relationship, that she can have sex with him whenever she wants, when she wants, and there wasn't anything I could do to stop it, unless I wanted out of the relationship, but interestingly she didn't want me to leave. She assured me of all the things she did love about me, just not my penis and how incompatible we were sexually. I confessed my desire to watch and occasionally she let me. I never forget a cuckold session but my first one is something I think of every day.
My first time watching I understood for the first time why she needed this. Her satisfaction meant the world to me. I kissed her forehead as her lover repeatedly entered her, touching her in places much deeper than I could ever even imagine doing myself. He completely filled her and when he had an orgasm he would stay inside her, often in a spoon position, until his still large semi erect cock plopped on the bed. It makes a thud noise that puts a smile on both our faces. It got crazier than that, one night even doing a cock comparison. He made me look and feel like a 5 year old boy. We both enjoy the humiliating aspects to cuckolding. She is constantly reminded how thankful she is each time she is with him and often compares us, knowing I get aroused and am able to orgasm too, but often quicker than I had previously. We both mutually are satisfied with the arrangement and nobody else would be the wiser. As a gift to me, she allows me to be teased and humiliated by other women. Our love has deepened and we rarely ever have arguments now. It's not for everybody, but it sure has rocked my world.
this is nice story, i like it! and i like more...
Great story! Thank you for sharing.