The story of my small penis

I was standing in front of Ingrid who was sitting on my bed. She put her hands forward and took hold of my belt and drew me closer to her. Ever so gently she undid the belt buckle followed by the button at the top of my jeans. She took one finger and softly put it behind my underpants waist band - my Jockeys were showing by then as my jeans had slid an inch or two down. She withdrew her finger and took her hands and lifted my tee shirt over my head, and my large hairy chest became visible. Next her fingers moved to the zip of my jeans, which she ever so slowly slid down and she could then clearly see my dark navy blue underpants which were very visible. Next she - wait let me rather start at the begining. Do you have something that you are affraid of? Heights maybe, or spiders or small spaces. All of these have names, but my fear does not, or maybe it does. I am affraid of people seeing me with out clothes. Stupid you may think, but for me very real and for good reason. I am 54, and even today I have this fear, almost a dread. Even going to the doctor about my foot worries me as he may ask me to remove my pants. The cause of this fear? I have a small penis. It is interesting that as I get older the more the size of my penis concerns me and the more I like looking at young guys. Lets start the story of about how I feel and how it all started. Growing up it was just my mom, gran and I - parents divorced when I was very young. I can remember when I was only six I saw another penis for the first time (I am also an only child), when we were at school changing for swimming. Way back then, at an all boys school, we all wore white briefs with a fly (tighty whities) as coloured undies had not come onto the market. When we were changing that day I noticed that a friends penis had changed, and it looked like mine. What I was seeing was that he had been circumcised during the holidays! I was cut at birth, but not for religous reasons. I still remember feeling "proud" that my friend and I looked the same. Sadly after all these years my flaccid penis still looks like a little boy's - even in diameter. It must have been when I was about 11, coloured underpants started to be popular - Y fronts and scants (very cut away at the sides). I was totally taken by these and went out of my way to look at the other boys to see what they were wearing - the start of a fetish or maybe underlying gay tendancies? Anyway my school career continued and until I was about 12 or 13 I dont seem to recall having any issues or comparing myself with others -proberly because we all looked similar. However in my final primary year we had two boys who were repeating the year and were a year older.Their penis looked huge compared to my little soldier, but were most likely average for their ages, but they were very hairy in the pubic area as well - I was totally hairless still. The following year we went to senior school and linked up with new boys who joined our school from surrounding schools. I had started to put on weight and my "manboobs" started to develope, and I became very aware of my body and total lack of development - except what my class mates called "my tits". I was so self aware that I started to make up stories so that I did not need to do any sport or physical activity. In the five years of high school I never once did PT or swam. Some of he boys must have realised something was amiss, so every year when the school doctor came to visit they would volenteer me. So off to the school doctor I would go, and on arriving the school nurse wold say off with your clothes but you can keep your underpants on. The doctor would use the school hall, so there would be about ten other boys also waiting. I was petrified of the experience, so would slowly remove shoes, socks and pants and keep my shirt on - saying it was cold (these exams took place in summer). I would be called by the doctor who had a screen up, and get a blasting because I was wasting is time as I still needed to remove my shirt. We were checked for pulse, blood pressure and my personel favorite, genital developement - NOT. The doctor would pull down our undies and check whether testicles were okay and as we got older whether we had started to have erections. This was done to me every year of high school, instead of only a maxium of three times. But even with this fear I allowed something to happen that shaped my life - not in a good way I may add. I went to a friends house and started to chat to his sister, who was 16 to my 14. My friend had sort of implied that his sister liked me, and in my hormone filled mind I was flattered. It never dawned on me that my friends sister was just looking at having some fun. My friend and I were the same age but he was pretty well hung at this stage, so maybe his sister thought I was as well. Thinking back now I realise that I was damn stupid, knowing full well that my penis was like a little acorn - I had not, or even knew how to masturbated. Anyway one thing led to another and we went to her room to "chat". We sat on her bed and after a while she lent over and put her hands on my shoulder and lifted off my tee shirt. She seemed a little surprised at the size of my chest but never said anything. She took her finger and slowly traced my chest, gently touching my nipples which started to firm up - something that had never happened before. She took off her blouse, and it was the first time I saw a girl in a bra. We continued to chat for a while, but she eventually asked me to stand up and face her while she was sitting on the edge of the bed. I got up and faced her and she commented on my weight and whether it was part of my growth spurt - I now understand what she was really asking, and should have stopped right there. However, I said I thought it was possible and with that she leaned towards me and undid my belt buckle - history does repeat itself! I can still feel myself shiver with excitement and remember the feeling I was getting between my legs - a hardon!. She then undid the button of my pants, and ever so slowly pulled the zip down. My jeans stayed up, and she slowly put her hand into my pants and gently touched my penis. I noticed a surprised look on her face, but thought nothing of it. She then proceded to pull my jeans down to my ankles, and I was left standing in my tartan coloured Y fronts (somebody had given them to me for my birthday). I hated these underpants and at the time wishing I was wearing something else. What I do remember is that her brother always wore scants and these showed all you had. I was becoming very nervous now, and feeling very self aware. With one quick movement she whipped my underpants down and burst out laughing when she saw my tiny little erection! This experience had such an impact on me that up until two years back, nobody (and I mean nobody) saw me in my underpants, never mind naked. As mentioned before my school days were becomming a problem because of gym and swimming. We had to wear Speedos in the school colours for swimming and only shorts for gym.Well, you were wondering why I refused to swim or do gym. Looking back I realise that I was crazy as all my class mates knew about my little penis and man boobs.I then had a brain wave, and decided that instead of wearing briefs - by now I had progressed from white to colour as mentioned before, I would start to wear scants or bikini underpants. My logic was that because they were small and cut away they would "elevate" my penis and testicles! I have not mentioned the fact that my testicles are also small with the right one hugging my body, this I think is due to a hydocele I had at about 3. I am not sure why I thought of this because as I mentioned before nobody saw me without my pants on and I did no sport what so ever. Well my school career continued and because I was not doing any sport began to put on weight and the man boobs started to get bigger - it became a vicous circle. Fatter, bigger boobs and the fat pad at the base of my penis got bigger and my small penis got smaller! The only good thing that happened during this time was by chance I discovered how to masturbate, and what a thrill that was. I had heard my mates talking about "wanking and jerking off" and when ask if I did, I said of course - who doesnt (yer right). The first time that I had an idea of masturbating I was sitting in my room naked (I enjoyed being naked in the privacy of my own room when nobody was home). A small dribble of clear liquid appeared and I got the most wonderful feeling when I touched my penis with my finger. Well, I had seen my mates show the "O sign" for jerking so gave it a try. After a few strokes (most likely four or five) I had come for the first time. For the next 30 odd years masturbation has been just about my only sexual experience (more on that later). As I mentioned before I dont undress anywhere for anybody but for some strange reason I have a fetish for mens underwear. I have tried them all except boxers which I have hated up until now, but Jockey have a new range with the eleastic showing (like my briefs) and I have brought some - although wearing them would hide the little I have to show. I mainly wear mini briefs and in the winter trunks. It is strange that I like to wear all these types knowing full well nobody ever sees them - well nobody had until about two years ago (except that friends sister). I have a lady friend, Ingrid who started to visit more and more. At first few visits we would just talk, but after about the fifth or sixth time she suggested we lie down as it was more comfortable. This happened a few times and we slowly moved to summer. On one occasion she said that if I was hot why didnt I take off my shirt, which although relucant, I did although I left my vest on - my friend has a wonderful way of making anybody feel at complete ease. She teased me about wearing a vest (white sleeveless type like a tank top), but she never said a word about my man boobs, although even with a shirt on she could see them. She was taken with my hairy chest (the bit visable above the neckline of the vest) and playfully moved her fingers through my hair - I have a very hairy chest and back. After a while of playing with the hair on my chest and under my arms, she asked if I would I remove the vest. I am not sure why I made no excuse or reason not to, I removed my vest. She continued to stroke my chest and every now and again would lightly brush a nipple. After a while her hand slowly made its way down my chest onto my stomach and on towards my belly button. I was starting to get a little scared - what would happen if she went any lower! I asked her to please stop as I needed to get up. I noticed the look of disappointment on her face, but she accepted my excuse. Anyway we did not see each other for a week or two, but when we did she mentioned how nice it was lying together and her being able to run her fingers through my chest hair. I was a little relucant as I sort of thought I knew where we were heading (maybe relucant is wrong maybe I was hopeful), but as I said before I was very comfortable in her company. Anyway, we started to chat and for some reason I explained about my "problem" and that I had been laughed at before (shows how insecure I am) - not sure if it was a good move at the time but on reflection it was as she said not to worry about things that you cannot control. We started as we left off the last time, me removing my shirt (and vest straight away this time) and her running her fingers through my hair. Slowly she worked her way down to the line of hair that runs down from my navel to the pubic area. She then ever so gently took her fingers and moved my shorts (running type shorts not boxer shorts) down an inch or so - just enough for the elastic of my underpants to show. What happened next is hard to discribe. For the next ten minutes or maybe longer her finger gengly moved under the waist elastic, round the sides to my waist, up my sides onto my chest and lightly touched my niples. After a while she took her hand away and gently bent my legs at the knee (I was lying on my back) and ever so gently took a finger and put her hand up my shorts and traced the leg elastic of my underpants all the way round. By now my penis was staining against the fabric and I had become rather wet and because of the erection (which she never commented on) the leg elastic had moved away from my body and the finger slowly found it's way to the line between my leg and pubic area - I was on cloud nine. That was all that happened on that occasion as well as the the next few. Maybe she was slowly building my confidence for something that was still to come! On the next visit we started much the same - lying on the bed and chatting. After a while she took the lead and removed her top - my second view of a woman in her bra. She then said I should remove my tee shirt, which I did - I was not so apprehensive anymore. We lay there and we both gently touched each other for a while - my first time touching a woman. Her fingers slowly made their way "down south" and the fingers slowly played with my hair (I was also very hairy in the pubic area) under my underpants waistband. She then asked if she could remove my shorts! I cautionly said yes, but said would need to remove her skirt as well - bit unfair me in my underpants and her just with no blouse. Ever so slowly my shorts were pulled down and off, and I was lying in my underpants.Again her gentle fingers played with my waist and leg elastic - what a joy! I must say that she was so gentle and took things so slowly, but a good ten minutes later her fingers move lower and then gently touched my erect penis - through my underpants which had a large wet spot. After a while her fingers moved under the elastic and started playing with my pubic hair and hair on my scotum. After what seemed like a life time her hand slowly touched my whole penis - at 49 the first time a woman had ever touched me!. She eventually brought her hand out and it was rather wet, she smiled and asked if I was okay. Okay! I was over the moon! Thats as far as we went this time even though I was aching for more. I must add that even at this point she had not seen my penis as it had all been by touch. This little play went on for the next few visits, but the time came when we were both in our underwear. First she removed her bra and then my shorts. Then followed her panties - my first view of a naked woman! Although I think my mind was more concerned about what was most likely going to happen next. What then followed will stay with me for ever.She was tracing the elastic again and gently touching the bottom of my scrotum and the very tip of my penis, but eventually asked if I would mind if she could remove my underpants - which again had a large wet mark. At first I was very apprehensive as although I loved her touching my penis and testicles she had not seen me completely naked, and I did not want to be laughed at again. She reminded me of when I asked her to remove her skirt as I thought it unfair that I was in my underpants- hell, women have good memories! Full of fear I agreed and ever so slowly she removed my Jockeys (red with a white waste band - I remember as though it was yesterday), down to my knees and off my ankles. She never said a word, but continued to gently touch the tip of my penis, working down and gently squeezing my testicles. This went on for a while, but then ever so slowly she started masturbate me! By now I was almost accepting the fact that she had seen the little I had and lay back and enjoyed what was pure bliss.WHAT A JOY!!! You would think that as this was the first time a woman had touched me, that I came quickly - the reverse was true. After 10 minutes (yes, TEN) I had still not come although I was in heaven and had a full erection the whole time - was it apprehension or that she did not use the same presure or speeed that I used? I eventually took matters into my own hand (literaly) and finished off with semen flying onto my stomach. We lay togther for a while and eventually showered together.We did the same thing for a couple of weeks and then she asked if I would masturbate her! This was something completly foreign to me, as I had only just got used to seeing a naked woman. We started as we always did, she removed her blouse and my tee shirt, followed by her skirt an my shorts. She got onto the bed wearing pink cotton panties and a black bra, and I was wearing my usual Jockey mini briefs. After lying and just gently touching each other she asked me to see if I could remove her bra with one hand - I was super keen and it was off in a second! She gently took her finger to the elastic of my underpants and slowly pulled them down and out popped my erection - ready for action although it was not required. She then took my hand and placed it in her panties where I could feel the warmth of her body and the short pubic hairs. After a while of me just touching and feeling my way round she removed her panties and asked if I wanted to have look - this I did as it was my first real close encounter with a vagina. She then took my finger and guided it into her warm and wet vagina and ask that I gently moved my finger around. This I happily did for a while, and as she slowly got closer to organism,she gripped my penis and started to masturbate me - and although aroused I had lost most of my erection - was this a sign of problems to follow? Needless to say after much moaning and excitment, her body went ridgied and she let out a sqawk as she came. My erection was back and although she tried her best (and I was getting sore) I was only dripping precum at the end of it - I felt that I had let her down. On her next visit we did as before, but this time she said she wanted to try something on me. After the usual talking, touching, kissing and licking she rolled over and started to lick my scrotum. Ever so slowly she made her way up to my penis and started to tickle my glans with her tongue. Eventually my penis was in her mouth and I was having my first blow job! I have heard that the best feeling a man can have is a blow job. I do not know it its just me, and maybe because it was the first time, I did not think much of the event. Again she tried her best to get me to come - including sucking and gently nibbling with her teeth, but nothing. She is so understanding and thoughtful and she realised that although really revved up the only way to help me was the tried and tested hand job. On the next visit she suggested that we try intercourse! At first (we were still fully clothed at the time) I was extremely relucant as I did not have a condom (I had no used for them did I?), but she assured me that it was okay as she was on the pill. The usual ritual of undressing and kissing was followed by me trying to penetrate her. My erection was hard and throbbing as I entred her, but after a few thrusts it went soft and I had to withdraw and stimulate myself to hardness again Again I was a flop even though we tried me on top, her on top and doggy style but nothing worked. I was almost in tears (yes, I know it sounds corny but its true) as I felt that after what she had done for me over the months, when it came to me I was useless. The other point in my mind was that although I had entered a vagina I had not ejaculated so was still a virgin at 51!!! Even though she still came around she never suggested intercourse again and just masturbated me on each occasion - had she reserved herself to the fact that my small penis was just not up to it, or did she have a thought in the back of her mind that although I like woman I may also like men? We enjoyed each other as best we could for the next few weeks when we encountered a set back. We were both naked and had kissed, touched and caressed each other before she started to masturbate me. After about 5 minutes I was aching with anticipation before orgasim, when I said "I love you..." I started to orgasim at the same time so never finished saying "I love you doing this to me", and although she let me come we have never been naked, touched or become close again! So it was back to solo action for me, although I have started to create a little bit of excitment each time I jerk off. So what do I do? Well let me explain. I like to see myself when I masturbate so I have a large mirror that I put next to my bed. I lie fuly clothed on the bed and slowly rub my nipples until they stand up Next I take a clothes hanger and gently touch my leg, up the pants leg and flick my scrotum. This as well as slowly removing an item of clothing at a time lasts about 30 minutes. Eventually lying naked I mastrbate for 10 to 15 minutes before coming - as noted before what I lack in penis length I more than make up with staying power! Now at the age of 54, and still not really have had sex, I am still a virgin. Should I try a gay relationship as I think men are a little less particular when looking at each others bodies - or am I wrong? But I dont know how to go about this.