I met Paige when I was about 15. She in the year above my sister at school but played in my sisters softball team on the weekend. She was a nice girl and quite attractive albeit a tad plump. I wouldn't call her fat but she was probably carrying a few more pounds than she would like. If she lost those extra pounds she's be seriously hot but instead she was a cute girl trapped in a slightly larger body. I had no problems with that. It would be hypocritical of me to say otherwise as I'm carrying a few extra myself.
One night during the summer I was at a friends birthday party. It was a pretty big party with lots of people both my age and up to about 5 years older.. Being a tennage birthday party unsupervised by parents there was plentyof alcohol, cigerettes and pot being consumed around the place. I didn't smoke so I stuck to my bottle of Bourbon that I was probably drinking way too quickly.
"Hi Jack" came from one of those cute little high pitch voices that some girls had. Turning around I quickly recognised the girl as Paige.
" Do you remember me? I used to play softball with your sister"
"Of course I remember you Paige. It hasn't been that long since I last watched you play" I replied almost arrogantly. My sister had only stopped playing in that team the summer before so it had probably been just under a year since I last say Paige.
"Are you having a good time?" Paige asked
I really was fucking hopeless at talking to girls at this stage of life. This is probably a fair indication of why I enjoyed being with men. It was so much eaiser to get laid! Men don't want to chat. They just look at you, you look back at them and an hour later you have 8 inches deep up your ass. It's too easy!
Paige persisted in talking to me and eventually the conversation began rolling a bit smoother. She really was a nice girl with a good personality. She became easy to talk to after a while and when fear started leaving me. This may have also been due to the extra Bourbon.
The night wore on and I had been talking to Paige for what must have been a few hours. Mainly talking about school, sports and unfortunately my sister.. Then.....
"I think you're cute" She says out of nowhere. I don't know if it was the alcohol in her or what but she just randomly hit me with that. I was pretty happy with myself and it seemed to fill me with some bravado all of a sudden.
"I think you're cute as well. I always have ever since I first saw you" I reply. It may have been too much to say. Perhaps just a thanks I think you're cute would have been enough but regardless it seemed to be something that she was happy to hear and within seconds we were having one serious kiss. And boy was it nice.
Out of the corner of my eye I could see one of my friends looking at us. He had a look of utter shock on his face. I was the chubby boy. I didn't get the girls at parties like soe of my friends did. But now I had; and she was also older! three years to be exact. Yeah i rocked right now!
The party finished and me and Paige were still having a fantastic lip lock. Then it hit me. Fuck, what do i do now? We can't go to my place and i had no idea about her living arrangements. As Homer Simpson would say, DO'H!!!!
"Jack, I have to go home. I'm getting a lift off one of my friends." It wasn't exactly an invite for me to come with her.
"Oh, ok then" Was all i could come back with.
" I've had so much fun tonight talking to you and it as real nice kissing you" She says.
"Me too" was my lame ass reply again. I was too shocked and disasapointed at the abrupt halt to proceedings here. For a moment I actually thought I was going to get to have sex with a girl. I should have known better.
"Have you got a mobile phone on you?" She asked. " Put my number into your phone"
And I did as she quickly gave me a kiss on the lips and then departed for her friends car.
This was bad enddig for a few reasons. No sex for me on this occasion and more importantly, if I was going to get sex from her I now how to do the hard work and call her. Shit! This sounded way too hard. I mean, i have called men many times to organise a fuck session but the was more like dating. I'd never had to do this and wasn't sure if I actually could.
I got home that night and went to bed. I still felt a bit drunk so i decided to send ehr a text message while the confidence was still there. It was short and simple. "I really enjoyed tonight. i hope we can do it again soon"
"Me too" came the reply shortly after. It was a nice reply to get but it would have been nicer if it said "Me too. Meet me at blah blah blah tomorrow night." Then I wouldn't have to be the instigator of this potential meeting.. Geez i was weak, why did I have to do all the work. Because that's how it works dumbass, Toughen up!
I had to pursue this now while I still had any manly confidence in me. In the morning when I sobered up it would be all over. I'd be too shit scared again.
"Hey Paige. I'm going to #######'s party next Saturday night. You going to be there? It would be really nice to catch up again" There. I had sent it. It was as good as a proposition as I could muster.
"Yes I am going with some friends. It would be real nice to see you again"
"Ok, see you then. Have a nice night" i finished it with.
"You too"
I remember the exact messaging conversation because I kept it on my phone for ages and read it over and over.
During the ensuing week my parents adivsed me that they were going to my aunties place on the weekend. The house was mine!
The following Satuday arrived. I was at the party for a good hour before Paige arrived. I was real worried that she wasn't coming when she finally turned up with ther friends. even when she arrived it took her a long time to acknowledge me fully. There was a smile but she was too busy socialising with others to come to me. I started to get disheartened because I clearly did not have the testicular fortitude to go over amongst her friends and try and woo her away.
I was in the back yard talking to a friend from football when she came out the door on her own. It was go time. And i amost harrassingly rushed over to her. I wont go over the conversation again. It was the stadard, Hi how you doing? blah blah blah until i just leant in and kissed her. He didn't pull away or anythin and it was real nice again. By the end of the night I was really starting to like this girl.
"I was wondering...... my parent are away........would you like to come back to my house. My dad has some Whisky we could drink" If i was going to invite her back i obviously wanted to have sex with her tonight. I might as well get her even drunker to improve the chances.
"I'm meant to get a list home from Karen" She said as my heart sunk "But I guess I could tell her that you will walk me home"
I'm not sure if anyone has seen the movie White Men Can't jump, but there is a scene where they just win a Basketball game and Woody Harrison' character is all excited and he's dancing around singing "We're going to Sizzlers, We're going to Sizzlers, We're going to Sizzlers" Well that song started playing in my head over and over. To say I was excited was an understatement..
It wasn't that long as walk to my house. When we got inside I very quickly raided my fathers liqueor cabinet and pulled out the Whisky. I poured us both one. We sat and talked and starting kissing soon after. It was more full on than at the party. Both of our hands were doing a lot more wandering and exploring of each other. I was rubbing all up her leg and over her nice bum and her hands we doing like wise. If this were a man I was making out with i would be rubbing his crotch and making him nice and hard about now but I wasn't really sure what to do here. She actually made the next move and did exactly that. Her hand started rubbing my nicely over my rapidly erecting cock.
As this was happening my mind went into a moment of panick. God, what if she laughs at my small cock! what if she laughs at my shaved pubic hear and balls! My heart started pumping real fast. She knew people that I knew. Rumours start this way. Eventually the sensation that she was giving me took over my fear and I just relaxed and started enjoying it totally.
It was time. I stood up and grabbbed her hand. It was time to move to the bedroom.
Clothes started coming off real fast and it wasn't long before we were both doen to our underwear. I had mens briefs on by the way. It was a rarity. Luckily for me. But damn. I was in total awe. I love ladies lingerie and especially weraing it but having her stand ther elooking so amazing in front of me was driving me crazy. I should have been staring at her but I couldn't take my eyes of her panties and bra. It was an Aqua blue set that was not lacy but very sheer and see through. Fuck i wanted to wear them. I could see that she only had a very narrow strip of pubic hair and small pink nipples mounting her voluptous white breasts. This was very different for me but very arousing at the same time.
We climbed on the bed and started making out again. Hands were wandering everywhere onec again. I was all over her tits and ass and she was rubbing my now very hard cock.
"take them off" She demanded. Ok this was it. Moment of truth where she was about to see my small hearless cock and balls. Please don't laugh!
"Well well"She exclaimed. "Someones nice and smooth down there arent they" She said as my heart pounded like a machine gun.
I needed an excuse "My pubes kept getting caught in my underwear and I got sick of it so I shaved them off." I lied poorly.
"Ahh ok then. I think it's cute. I hate blowing a guy and getting pubes in my teeth" She said. I was about to say " Me too!!!" but had to bit my lip as this was not the place announce my love of cock.
At that she got her self into a comfortable position and started servicing my throbbing member. OH MY GOD!! this was good. I've been blown by guys before and loved it but her lips were softer than a mans and everything was more tender and not so aggressive like a male. All sorts of thought started racing through my head again. Does she swallow? Does she like it doggy or on top? Does she do anal? My answer to each as yes, yes and yes but she wasn't me. I'm sure i'd find out in good time.
I was going to undo her bra but paused for a second. I had unone my own bra so many times i was like and expert. Be clumsy about it I thought. Look more like a typical boy. I fiddled around a bit before getting it undone. She still seemed impressed that I got it undone eventually. Most boys cannot. But i'm not an average boy ; )
I wanted to see her pussy. I told her to lie on the bed. I kissed up her legs and slowly put my fingers in the top of her panties and gave them a gente pull. Slowly I pulled them down to her knees. Wow!!!! apart fro the little strip from the top of her pussy going up a bit she was cleanly shaven. it looked nice. I was going to eat her pussy. I kept kissing up her inner thigh adn eventualy worked my mouth across her pubic mound. I wasn't exactly an expert at eating pussy only from what I had seen in porno movies.
I have a pretty big tongue. I lowered it out from my mouth and licked across the top of her pussy. She moaned with delight. I gagged. Of Fuck!!!! I had sucked a lot of cock before but this was vey different. Not really sure how to say this but it fucking smelt real bad! once again I was in a predicament with myself. I didn't think i could do it without being sick. i felt real bad. She had jusy blown me and I wasn't sure that I could repay the favour. Don't breath while down there I thought. I licked her again while not breathing. She moaned again and I gagged again. DO NOT SPEW ON HER!!!! was all I could think.
I had no idea what I was doing and I'm not sure how many guys have eaten Paige's pussy but this surely was the worst time ever but she kept moaning and that was good enough for me to presume that she was at least enjoying it slightly. Even if I wasn't.
"I need you to fuck me now!" She almmost yelled at me. "Have you got a condom?" She asked
I always carried a rubber in my wallet. You never knew when you might get lucky.
I slid the condom on and positioned myself between her thighs. It was very different to what I was used to. Usually it was me that was preparing to be entered. I placed the tip of my little cock on her pussy and gave it a little push. In it slid. Very easily I must say. Within moments I had increased the rate of my thrusts as I pushed myself as deep into her as I could. She was moaning quite loudly and seemed to be enjoying it still and I kept pushing in and out of her trying to keep that pleaseure up.
"lay on your back!" She demanded. So I did. She placed her knees on either side of me and slid herself onto me again. She was grinding herself furiously against me. It wasn't so much a bouncinf motion but more so a back and forth grind. I must say it's a technique that I learnt off her to make guys cum quicker while riding them. after about 5 minutes her moaning increased. I think she was going to have an orgasm or at least fake one. A mighty moan released from her and her body went rigid and she collapsed on top of me. I honestly think she faked it but either way she wanted to stop and that was fine by me.
We laid there for a few minutes, "Thats was real good" She said or lied.
"Sure was" I replied
"You ready for me to finish you off?" She asked
"Sure am" I replied
Paige climbed off me and moved herself between my legs. She pulled the rubber off my now semi erect cock and started giving it a nice jerk. I was hard again real soon. Paige sucked me so well again, it was fantastic looking down and seing her sexy eyes look up at me with my cock in her mouth.
"Open your legs a bit" she told me, I did. "Bend your legs a bit" I did. Paige lowered her head down a bit more and started licking on my balls. "Mmmmmmm Smooth" she said. I just chuckled. She kept licking my balls and then started licking the bit under my balls between the balls and the ass.I started to get a bit nervous again. She kept licking the whole area and then I felt her arm move and slide under my knee. She put her finder in her mouth and made it real wet.
"Holy shit!! She's going to finger fuck me!!!!!!" I thought to myself. Usually I'd be all for it but I was scared here. I didn't have the usual tight ass of a normal guy. My ass was loose. My ass had had many cocks drill it and her finger would surely figure this out very soon when my ass gladly sucked it in.
Her finger starting working its way from my balls down towards my loose ring. I was tensing up trying to tighten my scphincter as much as possible. I still don't think it would be enough. She got to the edge and started circling my hole. She was looking up at me while sucking me with this cheeky grin. I must have just looked like I was in a state of panic and she was loving it.
In it went. Without hesitation. She was up to her knuckle within moments. No pushing was required. She knew what she was doing. She bent her finger and started strking it up and down my prostate region. Damn I loved this feeling but I was too scared to make it look like I was enjoying it that much. With her finger in me she now started sucking me frantically. Her head was bobbing up and down in quick time. It didn't tkae long. I was ready to explode.
"I'm going to cum!!" I yelped as she pulled her head away (that answered one of my questions from earlier) and I started shooting up in the air from my wet cock. While I was cumming she was pushing her finger real hard into me, pressing real hard on my prostate. Even after I stopped cumming her finger was still in there. I'm thinking "You can take it out now" Usually I wouldn't care if someone left themselves inside me for as long as they wanted but once again this was different. This was meant to be hetro sex. She pulled out a few seconds later.
Laying on the bed I was thinking to myself "She hasn't said anything yet. I think i have gotten away with it"
We laid there for about 5 minutes just relaxing. her hands were still rubbing my leg and she was staring at me smiling. I smiled back. I was in the clear.
"So you like men as well do you?" She asked.
"What, what do you mean?" I was on the back foot here. I had to deny everything.
"You know what I'm talking about. I know when a guy has a virgin ass and yours certainly wasn't virgin. And it certainly hasn't just had the occasional finger in there"
"Maybe i'm just naturally not that tight?" I was trying to fight this but was clearly on a losing battle.
"Hahaha" she just laughed and rolled over. "Give me you hand" So i did. She took my finger and ran it down hr butt crack pushing it onto her asshole. "Feel familiar" she asked
I was stunned. Paige was certainly no anal virgin either. The sex had made her wet all over down there and my finger slid straight into her ass without even the slightest push.
"You can't lie to me" She cheekily said with a develish grin.
I was just totally stunned. Lost for words and I laid there slient for a moment. I had nothing to say. my face must have bright red. I was sprung. It was all over for me.
"I think it's so hot watching two guys going at it. It makes me so wet." This girl was showing her true colors. I had liked her before but within the last few seconds I think i was falling in love with her.
"I'm not gay" came the standard denial excuse from me. "I like dressing up as a girl" I had been found out so I may as well tell her everything. Plus she seemed to like it.
"Really!?" she excitingly asked. "Do you wear your mums or sisters clothes?"
"No I have my own. I used to wear my sisters and then i took some of the girl that used to live upstairs from the clothes line and now I have my own that some of the guys that I have been with have given me."
"Dress up for me!!?" the excitment was filling her eyes
"Ahh....ok" I said. And with that got up and went to my wardrobe and got out my little bag of goodies which contained most of my womens clothes.
"What do you want me to put on?" I asked. By now all fear was gone from me. I was in my element now. She was enjoying it and as was I.
"What have you got?" As I laid it all out on the bed. "Ooooh, this, this and this"
She had chosen and black singlet, short loose black skirt and a red thong and bra set. Good choice I thought.
"I'll be back in a minute" and I went to the bathroom to get changed. I took my bag with me as she hadn't seen my wig yet. I also had my lipstick and make up in there. If she wanted a demonstration i was about to give her all i had.
"I'm just going to call my flatmate and tell her that I won't be home tonight. She worries about me when I don't come home until late."
"Ok" I yelled from the bathroom
I could hear Paige on the phone as I was getting dressed. It was faint and muffled from the other room so i couldn't hear the cconversation.
I was dressed. It was time to put on the show.
"Are you ready?" I asked
"Yes, show me what you've got"
I opened the door and walked out. She had a smile going from ear to ear. She seemed to like what she saw.
"You look so fucking hot!" She said.
"Thanks" Was this real. Do women actually like this. She clearly did but it all seemed so surreal. She stood up and came to me and started hugging me. Soon enough we were making out.
"I love making out with girls" she tells me and then starts kissing me again. She really did seem to love it as well as we were really getting into it when her phone rang again.
"I have to take this. It's my flat mate again" She told me as she shot off into the next room. I could hear talking and then i heard the front door open.
"What the!" i was thinking and then the door closed and I heard footsteps coming back to the room.
"Jack, this is Ian. I wasn't really talking to my flatmate either time. It was just a surprise that I had for you"
"Hi Jack" said Ian. "Well aren't you the pretty girl?"
At first I was surprised but that surprise quickly became excitement. Ian would have been in his 50's. He was tall with thinning grey hair and was quite athletic looking for his age.
"Well it looks like it's party time!" I announced. "Please call me Jacki. Jacks no longer here"
"Ooh Jacki, I like that" Paige said approaching me again. Within moments she was all over me again. We were making out again and from the corner of my eye I could see Ian walking towards us as well. He moved around us and behind me. I could feel him press up behind me and then his mouth was down at my neck kissing me on the neck while Paige kissed my mouth. Ians hands were rubbing me up and down my outer thighs while occasionaly slipping around me and grabbing Paige on the ass and thighs as well. This was getting real hot.
Ian grabbed my head and turned my neck to face him. He started kissing me hard on the mouth. Paige took over kissing my neck and and every now and then Ian would pull away from me and kiss her as well. These two certainly were not strangers to each other.
" On the bed Jacki" Paige demanded again. I was so in lust at this moment. My blood was pumping and I was up for anything. I laid on my back on the bed. paige came and laid straight on top of me. She starting kissing me again.. I could hear Ian taking his clothes off. It didn't take him long. He came and stood next to the bed where our heads were and I looked up. He was totally naked and he already had a very hard cocck standing at attention. And boy what a cock it was. It must have been at least 10 inches. He was also completely shaven. Just like myself.
Paige grabbed his cock and instantly put it deep in her mouth. Fuck this girl was a good cock sucker. This nice girl that I had started falling for was not that nice. She was plain nasty. And that was even more intriguing. Paige was sucking Ian so hard that the saliva started dribbling from her mouth down onto my face. Ian was catching it with his finger and directing it to my mouth where I eagerly licked it from his fingers. Paige kept sucking him hard. i would have easily cum by bnow if she sucked me like that. Eventually she had a rest and decided to share. She pointed his wonderful rod in my direction. I didn't need any invitiation and launched my mouth at it. It was big and it made me gag a bit as i took as much in there as I could. I just kept sucking and he kept fucking my mouth while Paige had hold of the base of his shaft dictating the play.
"Ian lay on you back" Paige demanded now of him. He got on the bed next to us and obliged. She wanted to be fucked again. I think she wanted a proper fucking not the little one I gave her earlier. She climbed off me and and straddled him instantly. No condom asked for this time. She definately knew him well. If I thought she moaned loud for me I had heard nothing. She lowered herself onto his magnificent cock. Inch by inch it buried itself in her cunt until there was no cock to be seen. She could certainly take the size easily enough.
I sort of felt left out for a moment but did not intend on keeping it this way. I knelt next to paige and cupped her left tit in my hand. Using my tongue i started circling her tiny pink nipple. This made her moan louder. I started circling it faster and then took the whole thing in my mouth and gae it a good suck. Gently I began nibbling on it with my front teeth. She was in ecstasy now. Ians massive cock was drilling deep into her and I was having my wasy with her left breast. I did not discriminate though and quickly gave the right one a go as well. While licking, sucking and nibbling on her right tit I gave her left one a tweak with my fingers.
After a while she looked at me. "Do you want a turn" I really didn't need to say anything and she just hopped of Ian.
Ians cock was real wet from Paige's pussy juice. I grabbed it with my hand and wiped off a fair but of the juice and reached around and pulled my thong to the side and made my fuck hole all wet and ready.
"Are you ready?"She asked as I started lowering myself down. She had hold of fim but the base of his cock and before I got there spat a bit more saliva onto his cock. I kept lowering myself until he was just inside me. Oooooohh it felt good as he opened me up.
"Keep going" Paige insisted, so i did until I would have been about 6 inches down. "Fuck that is so sexy!" Paige exclaimed from behind me. She had a close up view of Ians beautiful cock inside my fat ass. I could feel her head press against my upper ass as she started licking the base of his cock. "Go down further" she told me, so i did. About 8 inches in me now. She leant in again and licked what she could of his cock again. I could feel her tongue flick past my asshole in the process. "Fuck her Ian. Fuck her good!" and with that instruction Ian thrust his hips up into me even more unitl I had all 10 inches deep in me. All air pumped out of me and a quite large fart came out of me. They both laughed.
"Yeah, fucker her Ian!, harder, faster!" she kept demanding and Ian started drilling me furiously from below. he kept going for what must have been about 5 minutes when he started sounding tired.
"Have a rest Ian" she instructed him. I needed a rest as well. i had been bouncing around on top of him vigerously. Poor bugger must have been getting squashed by my girth.
"On your hands and knees Jacki" Paige was certainly quite dominant here. i liked it. I got on all fours on the bed. She positioned herself behind me. i could feel her hand working around my ass. One finger went in, two, three and eventually 4. She started fucking me furiously with her hand. It was going in and out easily as my ass was so wet by now.
"Do you want more!?" she asked me
"Yes, please give me more" I replied. She stopped with the motion and spat on my asshole. I could feel the thumb pushing its way in. "Oh fuck!" I yelled. She took no notice and kept pushing. ian had positioned himself in front of me by now and had shoved his cock in my face. It was wet, covered in the juice from Paige's cunt and my ass. I didn't care and I took it in my mouth again. Paige kept pushing from behind. It was starting to hurt as I felt myself stretch right open, then all of a sudden the pain stopped with what was almost a sucking sound.
"Im all the way in" she said with glee. The bitch had put her whole fist in my ass and was not up to her wrist. "How does that feel slut!' She wanted to know.
"Feels so good" i said almost in a trance. and it did. once the initial pain of the hand getting through went away it felt great.
"Suck his cock while I fist fuck you then whore!" she spat at me.
Ian pushed his cock deep into my mouth. he grabbed me by the back of the head and pulled my head towards him. I was gagging, saliva was going everywhere on my bed and i could hardly breathe. When he could sense that I could take no more he would let me pull back. paige started slowly. Gently pushing her arm into my ass. Slowly back and forth until she was just about to pull out and then deep back in past her wrist again. this was amazingly slutty and I loved it.
Paige kept fisting me for about 10 minutes while ian choked me with his massive cock. Eventually she said "Your turn to fuck him again Ian"
He pulled from my mouth and she slowly started pulling her hand from my ass.. it hurt again as she slipped past the knuckles but then she was out.
"Look how loose your cunt is whore!" she angrily said. Ian I don't know if this slut will even feel you inside her now."
"Oh she'll feel it when I go so deep in her" without hesitation ian rammed himself into me. No slowly guiding in. Just put all 10 inches straight into all the way to his balls. He seriously fucked me so hard that I was using all my strength to stay on my knees.
Paige came up to the bed next to me and bent over in front of me. "Eat me slut!" she demanded. This was a bit more familiar. i didn't spend too much timeon her pussy this time i just ate her ass out like I would a guys. I shoved a few fingers in her pussy and one in her ass at the same time. She liked that. i put a second in her ass and started fucking both her holes. She was going off, her moaning was frantic as I finger fucked both her holes.
"I'm going to cum!" Ian yelped
"not yet!' screamed Paige and rushed over to him. She paid on the bed face up next to me and took his cock from my mouth. She pulled it fast and almost on cue he starting pouring his load into her mouth, and there was a lot of it.
"on your back" Ian told me
I turned over and Paige knelt above me. It was snowball time as she opened her mouth and allowed his cum to stream into my mouth. "Swallow it all" she demanded again. So I obliged again.
"You are the dirtiest little slut that we have ever fucked" She said to me with a massive smile on her face.
We cleaned up and ian left not long after. Paige and me started talking for a while.
"How do you know Ian?" I asked
"Do you remember Megan that used to play softball with us? it's her dad"
"What!?" I said startled
"One night when we were 15 I had a sleep over at Megans house. I had justt got out of the shower and opened the door slightly to let the steam out. He walked past and I saw him briefly look in as I was drying myself. He thenwalked past a few times and kept looking. the next time he did i gestured with my finger for him to come in. He did. We shut and locked the door. He fucked me in the bathroom while Mgan and her mum were downstairs watching television. When we came downstairs her mum asked where he had been and he said that he was on the work laptop doing some work stuff. I've been fucking him since. We go to orgies and he organises gang bangs with his friends all the time. I love being the centre of a gang bang. one time he wanted to do something different so I went into picked up this old gay guy I knew from work and we had a threesome. that was his first time with a man. He loves it now."
"Is he still with Megans mum?"
"yep, she knows nothing nor does Megan. I have had her call me on my phone while her dad is fucking me. It turns him on even more."
I was stunned. yet again on this amazing night.
I still fuck Paige and Ian to this day. we have had plenty of wild nights with the three of us and sometimes more. Originally I had a massive crush on Paige but there she's definately not the girlfriend type of girl. Just a real good fuck buddy.
I hope that you enjoyed this story. I try and write as much as i can when I have time and i love sharing. If you have any feedback I love hearing from people. Please send to looseboy_girl@yahoo.com.au
Jacki