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by Tomthumb

I have always known I had a tiny dick I suppose. When I was in grade school I was mocked by a classmate when he noticed I always struggled to find my penis through my underwear when at a urinal. During my teen years of course I masturbated a lot and my relatively small hands (I wear a medium glove) would nearly cover the length of my erection. In college a few people made note that my feet are on the small side for my height and build, I wear a size 10. Have I mentioned yet I am 6′ 1″ and around 280lbs.

It wasn’t until after college did I really start to realize that I really do have a tiny dick. When I finally lost my virginity at 24 years old (am I in the 1% club that didn’t lose their virginity by the time I graduated college?) I noticed I couldn’t keep a condom on for very long as they fell off easily and never came close to fully unfolding when I put them on. I wouldn’t date girls for very long which I don’t attribute to my size but just where I was in life and not looking for anything serious but I had a few partners over the years.

It wasn’t until I had a May/December relationship with an incredible woman did my understanding come to where it is today. She had been married before and of course had a normal amount of men before I came into her life. We had an incredible sex life, she always did what turned me on and I had just the right amount of passion that made her wild. With that being said it started to become apparent my dick was smaller than she was used to. I could really only fuck her in 2 positions, either missionary usually with her ankles over my shoulders bending her back all the way for maximum penetration or doggie style. My dick doesn’t bend much so her on top wasn’t really an option as it would hurt me quite often. When I would try other positions I couldn’t get in very deep, just usually past the tip or I would fall out a lot during thrusts. Even with normal sex I would fall out of her very often but it wasn’t anything to be concerned with since it happened on a frequent basis and we loved each other so who cares.

It wasn’t until maybe 4-5 years into our relationship did I start to ask her if I was small. She would always say no but if I asked if I was one of the biggest guys she was with she wouldn’t lie and told me not at all. She had been with a guy that was hung like a horse years before us and right before we met she had a relationship with a guy that had a pretty large dick too so she knew what big was. I would ask from time to time and she always stuck to her guns. Lets face it, she loved me and didn’t want to hurt my feelings.

I started to get tricky with how I asked questions and I finally tripped her up to the point where she knew I wanted to hear the truth no matter what and started to come clean. I caught her off guard one day when we were talking about past partners asking if they fell out of her a lot during sex to which she replied of course not without hesitation. I then asked her was she used to switching sex positions during an interlude to which she also replied of course. I then asked would the guys usually come out of your pussy to reposition from say doggie to side saddle or missionary or even switching orientation to the degree of her on top. She paused for a minute to think and said most of the time they would stay in her but not all the time. She then started to give me looks to try and figure out what I was up to. I then asked her a final question before I put the screws to her. I asked when a guy would cum inside of her would the cum rush out of her pussy and drip out quickly or did it usually take a while. She looked at me and said the truth, most of the time it usually took a while or even sometimes not at all.

I think at this point she knew she had been tricked into telling me the truth about my dick. If I had had asked her the same questions about her and I all of the answers would have been the opposite of what she said. I then ran down the questions asking her about me…

Q) Do I fall out of you often during sex?
A) Yes but I squirm a lot and you often move quickly (she was trying to “fix” her answers).

Q) Do I stay in you or fall out of your pussy when we switch positions?
A) Yes, you always come out when we switch positions.

Q) From any position to any other position like doggy to on your side?
A) Yes

Q) When I cum inside if you how long does it take for my cum to dribble out of you?
A) Instantly

I asked other questions and her answers kept getting shorter and shorter and she was looking at me squarely in the eye. She wasn’t trying to make me feel badly but actually trying to get me to stop. I had asked her many times during the questions to please be honest with me. I can handle the truth and already know what the truth is. This was a different conversation from times past, she was being honest with all of her answers.

I then went for the jugular…

Q) Am I smaller than your ex husband (I already knew he was bigger than me from past conversations)?
A) Yes, you are smaller.

Q) Am I a little smaller or a lot smaller than him?
A) You are a lot smaller, and it isn’t close, I know that is your next question.

Q) Didn’t you tell me he was the smallest guy you had been with in your life?
A) Yes

Q) What does this mean about my dick to you?
A) You are the smallest guy I have been with in my life…by a long shot.

She started to apologise as if she hurt my feelings but I told her to not be silly. It is as if a weight had been lifted from over me. I knew the answers, I knew I was small…hell, I knew I was more than just small. It was a relief of sorts to actually hear it from not just anyone, but from a person I loved more than anyone else and to know she felt the same way about me. These were just the facts and it was what it was, no sugar coating it.