My first time was with a friend when I was 14.


I am the youngest in  a family of five where fifteen years separates me and my oldest sister.    My sister friend Jenn was a totally hot 27 year old who had most guys wishing she wasn’t a lesbian.    She did however experiment with guys and she ended up getting knocked up at 15.     Her daughter Sandy and I grew up more like siblings since our sister typically watched us as they hung out.     I can’t say I always viewed Jenn as hot but I certainly did when I was 14.     She would come to the pool in the smallest of thong bikini’s and even though I seemed to have a perpetual woody she always seem to make it a little harder.    My friends and I would watch nearly every move she made I bet I wasn’t the only one running home jerking off.    Unlike her mom Sandy was cute but plain and she was more of one of the boys  who always came over to us at the pool which mad us shut up about her mom.  
Sandy was a late bloomer and at twelve she showed no signs of her mom’s perky tits.    I had as much desire to have sex with her as I did with my friend John but that ended up changing.      It happened when I went to over to house before heading to the pool.     She wanted to go so she went to get changed as I went and took a leak.    When I walked out of the bathroom I found her running around the house without out any cloths.    I asked what she was doing and she simply said “Looking for my suite”.    All I said was “Without cloths?” and she started talking about how we have seen each other nude before.   Okay that was like when where kids but I was not going to argue with a girl who didn’t have a problem showing me what one looks.

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     Like I said she wasn’t built or anything but all those days at the pool had her very tan with a very white butt and an outline of a bikini top where her tits should be.    Her slit was just that and looked just like it did when I last saw it.   I watched her run around and then  I went into the bathroom and returned with her bathing suite that had been drying in the tub.    I held it up and told her I found it but when she came over to grab it I hid it behind my back as a joke.      We played the little this cat and mouse game as she jumped around trying to get her bathing suit.      Even though she had done nothing for me before I sprung woody as I found my eyes focusing only on her slit.     Then she grabbed my shorts and pulled them down to the floor and out popped my woody.   Unlike her I had developed and like most 14 year old guys I had pubic hair.    She stopped for a second and then said simply said “Wow that looks different”.   She then put her hand around it and I stepped out of my bathing suite thinking she was going to jerk me off.    Instead she took my shorts and ran away with me in hot pursuit.     I caught up to her and in the living room and I pushed her down on the couch and told her how that was unfair.   She told me “All is far in love and war”.   I said really and grabbed my dick and with a little fumbling guided to the entrance off her slit and pushed.    Her look was of surprise as she bit her lip, I felt pain and incredible heat but none of that register because three things happened; We both had sex for the first time,  I came as soon as I entered and her mom walked in.

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     I don’t recall everything that was said but “What are you doing to her”, “You stupid ass” and “Get the fuck out of her” was some of what I caught.    I grabbed my cloths and streaked out the door and into the hallway.    When I thought I was at a safe distance I started to get dressed only to get busted but a girl is my homeroom.    She started blabbering about never seeing a boy without out cloths but I was too busy trying to get home.   I got home as fast as I could fearing Sandy’s mom was already on the phone with my parents.   
I got home and everything seemed normal and I spend the rest of the evening jumping at every ring of the phone.   I went to bed and jerked off thinking about what happened.   The next day I faked sick so I could avoid Sandy but that I ended up meeting her the very next day.    I asked if she hated me and she asked why.    After  me saying “you know” about ten time she asked “Why because we had sex?”   She then told me she was surprised it  happened but not upset.   I then asked about her mom and she told me she wanted to kill you for not having a condom.   Her mom ended up being very cool about things and from that point on she allowed me to go into Sandy’s bedroom where we got undressed I got on top and shot my load and off to pool all within five minutes.      I guess my speed pissed off her mom because  after about two weeks she followed us in and asked me “Would it be possible to think of her rather then just yourself?”.    I didn’t really understand her at the time since after all we both seemed to enjoying the 60 seconds of pleasure. .

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     Her mom then said there was other ways to please a girl and she open Sandy’s pussy lips pointed out her clit and then Sandy’s mom started to lick it.    A Sandy squirmed I found myself getting hard so I pulled down her mom shorts and panties.    She didn’t offer and resistance I was looking at the most beautiful ass I have seen to date.    As Sandy’s mom continued to service her I got behind her mom and prepare for entry.    With that her mom turned around and smacked me right across the face and asked me “What the fuck are doing?”    I stepped back as she return to Sandy’s pussy,  figuring I knew what I was suppose to do I got up behind her preparing to lick.    She got back up and grabbed me by the chin and said “Listen you dumb dick,  I am trying to teach you how to please my daughter not to cheat on her!”.    Her mom then pushed more between Sandy’s legs and I got to taste my first pussy.    I got explore Sandy for all her glory and her mom even showed her how to suck my dick by first demonstrating.   
It was great summer and I learned a lot but as soon as school started I was jumping on any girl my age or older willing to give it up.    Sandy and I have remained friends and she has developed some over the years but what she lack physically she make up  for sexually.   On the night of here 21st birthday we got wasted and we did another first and she allowed me to be the first in her ass (Sorry Jenn no condom).  My current girlfriend has talked about being with another girl and I’ve been trying to get Sandy to help us out since my girlfriend is not into anal and it’s been two years and many jerk off sessions since Sandy allowed me to enter her.