Gay stories: Winning over my old best friend – Chap 2
After a night of thinking about all the possibilities, I decided not to make a move and try and let our friendship grow a little. There was method in my madness:
1) I still didn’t know how he felt about homosexuality, because if he wasn’t fine with it he may beat me or something.
2) Even if he was fine with gay people, it doesn’t mean he is one so if I did make a move he might take it badly, and it’s not like he can just leave the remainder of the night would just be awkward. And
3) Even if by some miracle, he is gay and likes me and ends up fucking me, my parents room is below mine and I know I would be moaning and shouting his name. As soon as I told the girls this, they seemed sad about it but then understood my reasons for not doing it.
It was now just before lunch on Friday and I was sat in Spanish waiting for the bell to ring. Eventually after the long torcher the bell rang and as I was walking out then Harry caught up to me.
“Hey Harry, what’s up pal?”
“My mom wanted me to ask, what time is their train tonight?”
“What train, what about tonight?”
“Didn’t your parents tell you? My mom got tickets to some stupid play in the city so our parents are going tonight and spending the day in the city before their play and will be back about Sunday afternoon. That means I am staying two nights at your house and a whole day” My stomach went into a big knot, my heart started ponding, and I felt movement in my underwear from my eight inch pole which I hid with my Spanish text book in quite a casual manner.
“No, mom never told me but it sounds great” I lied. “I’ll send her a text and catch up to you in math after lunch.”
“Ok, see you then!”
I then texted my mom, she then confirmed just what Harry said. I instantly went to tell the girls, they got very excited and though that now I had no parents and that because no one would stop him if he walked out of the house, I should tell him. I still couldn’t decide. I found Harry and told him that his parents had to be at our house for six and they would leave shortly after. He replied with a simple “Ok”. In my mind I wasn’t go to do anything but my crotch had other ideas, I saw that Hanna had noticed but didn’t say anything.
I knew I needed to think things over, so I skipped my last two periods and told Alice to tell Harry that his mom needed him so went home. My mom was surprised to see me when I got home, but I just said that I had a headache and needed to sleep before tonight. She seemed fine with that. I ran upstairs and just paced my room wondering what to do. I decided that I would make my move. Oh God. So I cleared my room, changed my sheets, and had a bath.
Thankfully I am blessed with little body hair, and what I did have was quite blond so wasn’t noticeable. I got my shaver anyway and went all over, especially as close to my ass as I could get. I then thoroughly cleaned my ass hole making it all nice and clean and stretching it out a little which I enjoyed a little too much.
That was it, I was done. I texted Harry to bring some swim shorts to go in the pool, something he seemed quite excited about. That was it, I was ready. It was not 5:30; I put on my black Calvin Klein boxer briefs, a white t-shirt, and some grey jogging bottoms. I styled my hair so it looked good, but not too good that it looked like I tried. Then the doorbell went and my heart went into my stomach.
I showed him round my house and he seemed to be very impressed. I love my house; I have a pool and a tennis court. As well as the outside which I love, my house is over three floors, and I have the top floor to myself. I have my queen sized bed, walk in closet, and my massive bathroom with a shower big enough for four, and a Jacuzzi bath big enough for six.
After the tour we chatted for a while and then decided to order a pizza. Before I even realized it was 11:30 and we were both feeling quite tiered.
“Do you want to go to bed now?” he asked, as I was looking quite tiered but I really wasn’t, I just kept drifting off to the thought of us making out in bed.
“Sure, if you want to.”
“What are the sleeping arrangements?”
“Well you can either sleep on the sofa on the other side of the room, you can sleep in one of the guest bedrooms down stairs, or you can sleep in my bed with me” the last one I said in a joking manor.
“I’ll sleep in your bed, if that’s cool.” I was so shocked; he wanted to sleep in my bed. With me in it. Wow.
“Yeah that’s cool.” I waited for him to get into whatever he slept in, I was so happy when I saw; he slept in his underwear, which for this evening were a white pair of Calvin Klein briefs. We always used to like the same things. I did notice something different though, when we would change in the locker room after practice, his chest was quite hairy. But now, it was silky smooth like it had just been waxed.
I then got into my underwear and crawled into bed next to him.
My heart rate increased. I then put my phone on charge to see a text from Alice. “Hey, Harry left school at the end of math, he told Mr. Baston that he wasn’t feeling well.” Which made me think, why didn’t he text me earlier?
“Hey, Alice said you left early today, why didn’t you text me?” hi cheeks flushed, you could tell he was trying to think of an excuse.
“I had a hair appointment that couldn’t be changed; I didn’t want you to think I was queer”
I responded with a simple “haha”. I started to wonder if it wasn’t the hair on his head, but the ones on his chest. We were then just lying in bed together, realizing that we had talked about anything.
Out of the blue, he then says, “Alex, have you done it with a girl?” To say I was surprised would be an understatement.
“No not yet, what about you?”
“Once, but I didn’t really feel anything. I felt, incomplete.”
“You sound like such a fag”, I thought that might help me find out where he was with being gay. But that comment got more of a response that I imagined. His face went red, his eyes were going all around the room, and he put his knees up in bed so there was a big tent, which I began to think was covering up a different tent.
“Ok here’s the thing Alex, I think I might be gay.” OH. MY. GOD. My crush, the guy I had been friends with for more than 10 years was gay. This was my chance. I rolled over and slammed my lips on his. At first he did nothing and then began to kiss me back. I felt his tongue wanting to come into my mouth and I let it. We lay there for what felt like an eternity making out with each other.
I then pull back and say “Me too.” And we both began to giggle. We then looked into each other’s eyes again and began to make out more. But this time I got on top of him and had my legs either side of his waist and I could feel his long hard erection on mine. He then pushed me back and asked “Are you sure you are ready for this babe?” He called me babe. Oh my god. I nodded and we kept making out.
Our hands began to explore each other’s bodies and our erections. I threw the cover off of us and started to travel down Harrys body, eventually arriving at his dick. I began to rub it through the soft material of his underwear; eventually there was so much pre cum that you could see it through them. I then pulled down his briefs exposing his nine and a half inch monster as it slapped me in the face.
I looked into Harrys eyes who were staring back at me. I placed my tongue at the tip of his cock and licked down the shaft and to the base in one slow move meanwhile not losing eye contact with Harry until he threw his head back in pleasure. Then I put my lips on the tip and began to move my head further and further down his cock until eight inches were in my mouth.
I began to bob my head all the way up and all the way back down using my other hand to jerk him off at the same time, meanwhile Harrys hands were in my hair pushing my head further and further down until all 9 and a half inches were in my throat. He then holds me there treating me like the bitch that I wanted to be. I began to moan while his dick was in my mouth which drove him crazy. After a few minutes he had full control and was fucking my face which he enjoyed. He then said “I’m gunna cum”.
At that moment I stopped to his disappointment and took off my underwear and positioned myself on all fours showing him my boy pussy and said “I want you inside of me”, as soon as I did this I saw the big smile on his face and the pure animal lust in his eyes. He then started to lick my hole, circling it with his tongue. I felt his tongue going in to my ass which I loved, I felt like I was on cloud 9.
After a few minutes of him fucking me with his tongue and grabbed lube out of his bag, “Someone came prepared” I said to him sarcastically and he just smiled at me. He rubbed a good amount on my ass and on his cock, I knew it was time. I relaxed my hole as much as I good which seemed to help as he started to slide his dick into my waiting boy pussy, after he was half way in he kissed my back.
He eventually got all the way in and stayed there for a minute and let me adjust to this new sensation. When he first went into me it hurt a little but as soon as he was all the way in, the pain became pure pleasure. He pulled almost all the way out and slammed back into me. Hard. I loved it. He kept fucking me and I was moaning like a little bitch.
“Say my name.”
“OOOHHH H OOHHH HARRY”
“Yeah say my name, you love this big cock fucking your virgin pussy don’t you”
“YES OOOHHHH YES!”
He then slapped my ass, hard. I loved it I mounded even louder, which made him do it more and more. Then I felt him out of me and before I knew it he flipped me over and was back fucking me hard again. I then saw his eyes and the raw animal passion that was in them. He then bent down and passionately kissed me, and I felt the sweat on his face and he felt the sweat on mine.
He placed his hand on my cock as we kissed and began to jerk my cock which sent me into a new world of pleasure. After a few minutes of him jerking me off I felt like I was about to cum.
“Ooohh Harry I’m about to cum” As soon as I did this he slowed down his thrusts but increased the speed of his hand. That was it I came all over my chest six thick ropes of white cum landed over my chest.
“Ooohhh yeah I’m gunna come too”
I then felt his cock explode in my ass, a feeling which I loved. He then stopped thrusting and let his dick go soft in my ass and left if flop out. He then started to lick and suck all of his cum out of my ass. Then he gathered up all he could of my cum into his mouth and swallowed a little. He planted a big passionate kiss on me and I could feel a lot of our cum was still in his mouth and then he passed it to me. As he pulled away from the kiss, a long line of cum connecting our lips. I swallowed the mixture very happily and Harry then collapsed on top of me as we caught out breath.
It was an hour later and I felt something move on top of me, it was harry. We both had fallen asleep and we were both waking up. As he stood up my cum was obviously still there as lots of little lines connected us. He stool there in front of me with a huge smile on his face, he then suggested a shower. I only too happily accepted and followed him to the bathroom holding hands. It was fair to say that I was the happiest bitch in the world at that moment.
Other Chapters: Winning over my old best friend
- Winning over my old best friend - Chap 2