Second time

My second sexual encounter came 6 years after the first and again left me in no doubt that I was lacking in the trouser department.

In the 6 years between my first and second sexual experience I had had a few girlfriends but never got beyond the kissing stage as I was always very conscious about my little secret.

I was 18 and had started hanging around with a new group of friends I meet through collage. After a few weeks I met Sam at a party. Me and Sam ended up  spending a lot of time together and going on a number of dates. This relationship took the same route as all the others lots of kissing and not much more, I always made sure when we were together we were never alone so things never progressed beyond the kissing stage.

After a couple of months Sam managed to get us alone time at a friend’s house after a party. We were alone and I was out of excuses, we started kissing and before long her hands were all over me. I followed suit and it wasn’t long until we were both standing there in our underwear. Buy now I was full of panic and dreading her putting a hand in my boxers. My mind working overdrive I did the only thing I could think of, I pushed her down on the bed took her knickers of and buried my head between her legs and stated eating pussy for all I was worth. It wasn’t long before she was thrashing around the bed and gripping my head with both hands and grinding hard against it. I started to feel her shake and shiver as she moaned out and squeezed my head even tighter as she came. I slowed down and let her get her breath back before going for it again. I think she came 3 or 4 more times before she finally begged me to stop.  

After I had finished we kissed deeply and lay there cuddling. I waited for her to fall asleep and then sneaked to the toilet for a wank.

The following weekend after a house party we again found our self’s alone and when things started heating up I pushed her back and went straight for eating pussy. Again she came 3 or 4 times before begging me to stop and again I waited for her to fall asleep before sneaking out to the toilet and having a wank.

My parents were away the following weekend and somehow I let this info slip. Saturday morning I was woken up around 9am with Sam knocking on the door. I let her in and as soon as the door shut she was all over me. She took complete control and lead me upstairs to my bedroom. Once in the bed room she told me to “get on the bed”, I tried to turn things around and get her on the bed but she stopped me and told me quite sternly to “get on the bed now”. I obediently did what she said and got on the bed. She then stood at the end of my bed looked my straight in the eyes and slowly got undressed. I again tried to take control but she sternly told me to “Lay down”.  Once she was naked she started undressing me she first took of my t-shirt then my trousers and left me laying there with just my boxers on. She then laid on me and started kissing. after a few minutes of kissing she slowly started moving her way down my body  kissing as she went. She ended up kneeling between my legs and kissing my tummy whilst rubbing the inside of my thighs.  

All of a sudden she grabbed my boxers and pulled them down to leave my fully erect cock fully exposed. I could clearly see the look of disappointment on her face when she first saw it and registered its size but to her credit she didn’t stop and carried on. She took me all in her mouth and started moving her lips up and down my shaft. She sucked and wanked my cock for a  quite a while before getting up of the bed. She walked over to her bag and came back with a condom. She unwrapped the condom, put it on me and told me she wanted me to fuck her.  She laid on the bed and as I got on top of her she grabbed my cock and guided me in to her pussy.

I started thrusting away and was really started to enjoy myself until I looked down and noticed that I was no longer wearing a condom, I gave it a couple more thrusts naively hoping that somehow it would magically reappear. When it didn’t reappear I stopped, pulled out and told her what had happened. She seemed a bit confused at first and all I could keep saying was I was wearing a condom when I put it in but when it came out the condom was gone. When she finally realised what had happened she shot up of the bed and went the ballistic.

I just sat there on the bed feeling really turned on with her shouting at me about my pathetic little dick as she tried to find the condom and remove it. She finally pulled the condom out threw it at me, got dressed and left. Her final words before she left was that I should warn girls before getting into a relationship that I had a small dick and sex was nearly impossible.

Once she had gone I rushed to the loo and had a wank still with her cutting remarks ringing in my ears.

When I went out that night to meet my friends every one of them had found out what had happened with Sam and for the next few weeks I was constantly ridiculed about my dinky dick but for some weird reason this micky taking always turned me on.

First time

The first time I realised or should I say it was pointed out to me that I was lacking in the trouser department was quite a defining moment for me and pretty much shaped the rest of my life.

I was 12 ½ years old and was spending a lot of time with a girl that lived over the road from me called Ellie. Ellie was a year younger than me, she was a petite girl just starting to blossom into puberty. I would not call us boyfriend and girlfriend more Best friends with slight benefits. Those benefits would normally be holding hands, cuddling and kissing when nobody else was around, this side of our friendship was very secret and only between us. Although a year younger Ellie took complete control of our friendship and benefits that came with it. We kissed when she wanted to kiss, we held hands when she wanted to hold hands and I cuddled her when she wanted a cuddle.

Both my parents worked so I always had the house to myself for a couple of hours before they got home at 5:30. A couple of times a week Ellie would come over and we would spend those couple of hours laying on my bed listening to music, talking and kissing.

Every now and then we would both invite some friends round after school and again would normally sit in my bedroom for a couple of hours talking nonsense and listening to music.

On that fateful day I had 3 friends over Justin, Lewis and Russell and Ellie had turned up with her friend Kim. As was the norm the 6 of us went up to my bedroom put some music on and started talking nonsense. At some point in the conversation we ended talking about penis’s and how Ellie had only ever seen her little brothers and that Kim had never seen one. All 4 of us boys followed the penis talk by saying we had never seen a girl naked. After much discussion it was agreed that one at a time the girls would show us there’s and then we would show them ours. This was a very big moment and I can still remember the butterfly’s. Ellie we to go first, she stood up dropped a her jeans and then slowly lowered her Knickers. At that moment I saw the object of my life desire and was completely mesmerised by the little patch of hair she had. After what seemed like an age she quickly pulled up her knickers and jeans and sat down.

Us 4 boys were still wide eyed and slacked jawed when Kim stood up hiked her skirt up and pulled her knickers down again showing a beautiful little patch of hair. Kim dropped her skirt pulled her knickers up and quickly sat down. It was now our turn to show the girls what we had, we quickly agreed an order and it was decided that Justin would go first.

Justin stood up and dropped his trousers and pants, as they went down his cock shot up rock solid against his belly with a slap, Both girls let out a gasp and all I could do was stare at it. It was at least twice as long as mine and a good bit thicker.  I stated to get a sinking feeling as Justin waved it about a couple of times before putting it away and sitting down.

Next up was Lewis. He stood up dropped his trousers and pants and showed off what even to this day is one of the biggest cock’s I have ever seen. It was at least 3 times if not 4 times the length of mine, nearly as thick as my wrist and just stuck straight out in front of him. Both girls again let out a gasp when they saw it. Ellie nudged me and when I turned to face her she just mouthed the word wow. Lewis pulled up his trousers, slowly stuffed it back in his pants before sitting down, I just felt so sick and couldn’t believe how small I was compared to them.

Next up was Russell who stood up drooped his trousers and showed off a cock that again was at least twice as long as mine and at least 3 to 4 times as thick. Both girls sort of purred as Russell swung his hips and waved his cock from side to side. By Now I felt so pathetic and hollow inside I could barely stand. I Finally made it to my feet. I felt so sick and could barely feel my fingers as I tried to undo the button on my trousers.

Then without thinking I just ran to the toilet and locked the door and just sat on the bath. After a minute or so Ellie Knocked on the door and asked what was up. I made up some excuse about being sick and that they were going to have to leave. I just sat there on the corner of the bath feeling totally pathetic as Ellie told my friends they had to leave.

That night I laid in bed and all I could think about was how big my friends were and in comparison how small I was I even tried to stretch it hoping it would make it bigger.

The following day at school I made my apologies to my friends and told them I had been throwing up all night. I made no plans after school and intended to sit alone in my room wallowing in how pathetic I felt. I  was home for all of 15 minutes before Ellie and Kim were at the door asking to come in. I reluctantly let them in and we all headed up to my bedroom to go through the normal routine of putting some music on and talking nonsense.

I put some music on and then laid down face first of the bed in an effort to hide my embarrassment from yesterday. Ellie flopped down on one side of me and Kim did the same on the other side. We Started talking about School and friends then suddenly Ellie announced I still owed them I look at my penis and I needed to drop my trousers and let them have a look . I started to protest and before I knew it they were both on top of me pinning me to the bed.

Ellie took charge and said I could either give it up willingly or they were going to force me. I put up a fight and again refused, Before I could react the they had tied my hands together with my school tie and was in the process of tying my hands to the bed. Once they had my hands tied to the bed they went to work on my legs. They managed to wrap my bike chain around both my ankles and lock it to the bottom of the bed.

Ellie then demanded that I roll over onto my back. At that point I just lost all my fight and reluctantly rolled over. Once I rolled over the girls checked that I was still securely held and then began to undo my trousers at this point I just closed my eyes and resigned myself to the embarrassment that was about to happen.  Once they had my trousers down they started on my pants. As my pants cleared the end of my cock instead of the gasp’s they made yesterday all I heard was a little giggle. Kim asked “does it get any bigger or is that it” I painfully had to admit that no it didn’t get any bigger and yes that was it.

Over the next 15 minutes or so I had to lay there red faced as the girls took it in turns to play with my cock whilst telling me how small it was compared to the other 3 they had seen. At one point they measured it proudly telling me it was nearly 3” and even went as far as measuring it against various objects the my room. At some point during all this I really started to enjoy what they were doing to my cock and even the way they were talking about it. Towards the end Ellie asked “did I ever wank” when I answered yes she told me to tell her how. I talked her through how I gripped it and how I moved my hand up and down the shaft, Then before I could finish she had hold of it and was wanking it for all her worth. I Had Ellie asking me “is this how you do it” I had Kim asking me “does it feel good”. Then all off a sudden I let out a big yes arched my back squeezed my eyes shut tight and shot my load. Both girls seemed fascinated with how the cum shot out and began to interrogate me about how it felt, how far it shot and  how much normally comes out. I tried to answer as best I could whilst trying to get my breath back. The girls sat next to me for a good 5 mins or so watching the last of the cum to come out and then watching it shrink. Once it was fully soft they then started commenting about the size again and even went as far as measuring it telling me it was just under 1” when soft.

They finally untied me and let me go to the bathroom to clean myself up. when I came out They let me know that they had to go home.

Ellie came over a few more times over the next few weeks and on each occasion she would tie me up, strip me and play with me for about 10 mins before making me cum. During these occasions she took great pleasure in talking about my size, how big the other boys were and comparing me to various objects. She really liked it when it would go between soft and hard and even went as far as using ice cube’s to make it go soft and then wanking it until it was hard.  The last time she came round she told me she wanted to have sex with me so she got me to strip, tied me to the bed, she still had her school uniform on so took her knickers and tights off lifted her skirt up, squatted over me grabbed my cock and slowly lowered her self onto it. She rode me for about 5 mins got off, got dressed, untied me and left. A couple of days later she came over and told me that she wouldn’t be seeing me anymore or coming over. When I asked why she said that she had a boyfriend and had been seeing him for a couple of weeks. When I asked about us having sex she said “he had a much bigger cock than me and as she had never had sex before wanted to use mine to break her in as she had been told the bigger the cock the more it hurt your first time”

For the next few years whenever I saw Ellie or Kim around school they would always make a comment about size and give me a knowing look and I would always rush off to the toilets and have a wank thinking about what they did to me.