I really hope you enjoy this story. It is one of many that I have experienced over the past few years or so. I enjoy sharing them so please give me feedback at looseboy_girl@yahoo.com.au if you want to hear more of my adventures.
My father was quite a fan of the horse races. One Weekend we decided to have a family outing to the races. We all went my Dad, Mum and even my sister and myself. Also coming with us were one of dads work colleagues Les and his wife Sarah. They were an older couple, well by old I mean about 10 years older than my parents so that made them older to me. I had met them on one previous occasion so while knowing them I didn't know them real well.
We arrived at the track and made our way to the meeting point where Les and Sarah were already waiting. The standard greetings followed and my dad introduced my sister and me to Les and Sarah once again just in case we some how forgot who they were.
I was not really into the horse racing thing but it was fun every now and then to put on some small bets so the day was going quite well. I had backed a few winners. I was desperate to go to the toilet. The toilets had been packed all day so I decided to go in there mid race to avoid the crush. I took up position on the end of the trough and unzipped and released my tiny smooth cock. AS I started pissing a man stood next to me at the trough. I kept peeing and from the corner of my eye I could see him glancing down in my direction. He was having a good little look.
"Hmm very smooth and cute" he said to me quietly. I couldn't resist and had a good look down at him. He looked quite generously endowed, about 6 inches non erect. I just looked up at him and smiled as I zipped up my pants and walked away.
As I walked outside Les was just out the bathroom door,
" I was that man talking to you. He wasn't harassing you was he?" Les asked
"No he was ok" I replied
"I also saw you having a quick peek at him" Les said with a smirk
I was sort of flusters and tried to deny it in a blabbering manner. " It's ok Jack. We're all allowed to look at whatever we want" Les assured me once again with a mischievous smirk on his face.
I was semi confused. Was that a flirt or just a re-assurance that Les had just given me?
We went back to the group and all seemed forgotten, for now. Throughout the day I would catch Les giving me a sly little smile from across the table but he was a happy sort of guy and I also saw him flash a smile at my sister one or two times. Hmmm, I thought, maybe the sly old dog likes the look of both of us and is just seeing who he gets the best reaction from. I can tell you right now my sister wouldn't fuck him for a million dollars. She's all about pretty boy metrosexuals. OK maybe for a million dollars she would but you know my point.
It was the last race of the day. I knew that we'd be leaving after the race so I went for one last piss. I stood in the same corner and unleashed. Very soon after Les slid in beside me.
"well let's see what that other guy was checking out" Les whispered to me as he snuck a look. " yes very nice" Les said " Very clean and smooth" I looked over at him quickly. Wow! I thought. He was semi hard and already about 8 inches. There was no pubic hair to be blatantly seen so he was either shaven or trimmed nicely. This looked like a cock that I'd like to see more of. We both zipped up and made our way back but before we walked out the door Les slipped my his business card.
"Text my Mobile phone so that I have your number" he said. I looked and nodded agreeing.
The final race was over. We stayed for about another 20 minutes and then our farewells were made and we departed.
The following week went by, During the week I received several texts from different "lovers" (as per previous instalments of Loose Ends) but due to varying circumstances nothing came of them. But then on Thursday night I decided to be a bit proactive. I got out Les' Business card and sent him a simple text message. "Here is my number if you want it. Jack"
I waited for a reply but nothing came.
I was at School on the Friday and I received a text while in Science class. I couldn't check my phone as my Phone Nazi of a teacher would have confiscated it. As son as class finished and I was outside I read the text.
" Jack it's Les. Thanks for your number. Your dad says he be at races again this week. You going?" I hadn't intended on going again.
"No, I think it's just him and mum" I replied
"You want to have some fun?" Les asked in his response
I thought about it for a moment trying to analyse the risks that this arrangement could present but to be honest the more dangerous it seemed the more it excited me.
"I would love to" I sent
" Will you be home alone?" Les asked
"Yes"
" How does 12pm at your place sound on Saturday?"
"Sounds great" I replied with enthusiasm.
"See you then" came his final reply to which I did not respond.
Saturday rolled around. I'm always quite nervous when it comes to a new adventure and once again I had some minor nerves about this afternoon. To make matters worse he was bloody late. It was 12:30pm when the door knocked. I opened the door as Jack. I would have to scope out whether Jacki would be welcome to this party before I introduced Les to her.
" Hi Jack, nice to see you" Les said as I let him in. Les was not a real tall man. He was only about 5 foot 10, we were similar height and as with many men in their late 50's he had an expanding waste line and brown receding hair that had a slight tinge of grey to it. His face had no remarkable features and while he was not an overly handsome man he was hardly ugly either.
We went to the lougeroom and sat. I was playing this slow as I had to be certain as to what he wanted. We chatted for a while about various irrelevant issues before the conversation started moving into a bette direction.
" So how did you get into this" Les asked
" I was just curious and then one thing led to another" I told him
"Are you gay?" Les queried
"No I'm Bi. I have been with a few girls and liked them a lot. I think I'll eventually end up with a girl one day? I said to him.'
" Ahh ok then. That sounds very similar to me at your age" He said
" What about Sarah? I asked. Why do you still do this if you are married?"
" To be honest Jack. If I didn't do this we probably would not be married. * This* (he said doing the quotation marks with his fingers) Fulfils any needs I don't get from marriage and gives me that slight bit freedom" Les explained
" Fair enough then" I said accepting that answer.
Les moved over closer to me on the couch. He put one arm behind my neck and his other hand went onto my thigh.
"lets get to know each other" he said as his had started to explore my leg, rubbing up and down my thigh and soon into my groin. I responded and started giving him the same treatment, my hand gently massaging his upper leg. I was ready now and soon my hand began massaging his expanding bulge in his trousers. I rubbed his bulge for a while and he began to moan softly. It was tie for more and I started to unbuckle his pants and slide down the zip
Reaching into his pants I grabbed a hold of his member and pulled it out from it's hiding place. He was quite hard by now and it was certainly a joyous sight. Standing up from the top of his pants was about 9 or 10 inches worth of glory. AS I suspected from the races his pubic hair was nice and neatly trimmed with clippers and his balls were totally hairless. It looked fantastic and in my hand it felt fantastic. I gave it a slow jerk, up and down in a slow smooth motion and soon enough I was gagging for it. I wanted to taste his fantastic rod in my mouth. I leaned over to him and opened my lips taking the head in. I licked it all around the tip and then took more of it into my mouth until I had about half in. I sucked hard on it for a while and then went as deep as I could on it until I couldn't take anymore in my throat. I started working furiously on his cock sucking and licking it all over. His breathing and moaning was getting heavier and heavier,
I knew that he would blow soon if I didn't back off a bit. I pulled away from him and sat back and smiled at him. His face was red and he looked a bit short of breath.
" Was that nice?" I asked sheepishly
" Very, very nice Jack. You are very good for one so young" He complimented
" I just love sucking cock and when I do I want to make it as good as I can" I replied.
"Well consider that a success then Jack"
He reached over to my shorts and started untying the draw string. The shorts loosened and he started pulling them down. Surprise!!! I thought looking at him as once down it revealed my sexy little Black thong that I was wearing underneath. He looked up at me in definite surprise.
"Well, well Jack. What do we have here?"
"So when you asked me before If I was gay and I said bi. I guess I should have said I was tri if there is any such thing. You see I fuck both men and girls, well not a lot of girls as a guy but I have a real good friend called Jacki that really loved fucking men. Especially men old enough to be her daddy." I said very cheekily.
"Would you like to meet Jacki?" I asked. " If you don't I'm sure that I can make you really happy just the way I am."
" Well you really are full of surprises Jack. How about I ask you. Would you like me to meet Jacki or are you happy being here with me?"
" Oh I'm more than happy to be here. I hope you got that impression from that blow job I just gave you but Jacki is heaps of fun. She'll make us all real happy!" I said with glee.
"Well ok then. Let's meet Jacki" Les said and I got up.
" Ok give me 10 minutes and I'll introduce you" I said leaving the room Into my bedroom I went and I got my bag of goodies out from the cupboard. I got dressed as quickly as I could. On went the black bra and in went the fake boobs. I put a red sheer single over the top of it and a short black skirt. I had recently got a new pair of black fishnet stockings that I put on as well. I put on my wig and hastily did my make up. I didn't go overboard with the makeup. Some eye shadow, blush on the cheeks and a little lipstick. I was done.
"Please come in Les" I called out
Les walked into the room and I received the reaction I usually get when people meet Jacki. He just stared at me with a smile for about 10 seconds before finally saying.
" Hello Jacki, it's a pleasure to meet you"
" Hello Les, the pleasure is all mine" I said with a wry smile. "Please join me on the bed"
Les came and sat nest to me on the bed. Our hands once again started exploring each others legs. Les hands felt real nice through my fishnets and he seemed to be thoroughly enjoying it as well. He was still very hard and before too long I wanted him in my mouth again. I laid hi on his back and positioned my head over his glorious package. Near instantly I was deep throating all of him that I could again furiously sucking and licking away at his magical toy. I kept sucking for a while and as was before he started to breath heavily again and I sensed an explosion that we weren't ready for so I stopped.
" So Les" I said looking him in the eye, " I bet you really want to fuck me don't you?"
" Yes Jacki, I want to be in you" He almost begged
" Do you, do you want to put that big cock deep in my pussy?" I toyed
" Yes Jacki, I want to fill you up with my big cock"
" Would you like me to hop and ride your big cock like a good girl, taking it all in and then slowly taking it all out? Does that sound nice?"
" Yes Jacki, please ride my big cock and take it all in" he once again pleaded. I literally had him in the palm of my hand as I squeezed tight on his rod. " Hmmm, ok then, show me what you got" I said seductively as I straddled both legs on each side of him and positioned my eagerly awaiting hole above his throbbing member.
I spat on my hand and rubbed it all over his cock and then around my hole making it nice and wet. Slowly I lowered myself down. I felt the tip push through my opening. It popped through as the head went in. I moaned in ecstasy as I love the feeling when the cock first pushes through. Slowly I went a little lower and stalled. Then a little lower and stalled again, gradually repeating the process until I was sitting on the him with all 10 inches deep in me. I just sat there adjusting to the sensation. It was deep. I could feel it filling me right up and my body needed to relax and adjust. Soon enough everything felt right. My ass was stretched wide and I could feel his cock right up inside of me. It felt great as I starting rising up for the first thrust. I rose right up to the tip not quite allowing it to come out and then I slowly lowered myself right back down taking it all in again. I did this a few times watching his face as I worked the whole length
of his cock with my sluttly young ass.
" Give it to me" I demanded as I raised my hips up again. He welcomed the command as he forcefully thrust his hips up and slammed his rod into me. I jolted as his force was strong. It was heavenly. He started at a steady pace, not quite as powerful as his first thrust but each thrust was mighty and knocked the wind from me. I could feel the tingle on my prostate as he gave me a good fucking while I rode him like a good cowgirl.
My phone rang. It was on the bedside table.
"Don't worry, I'll let it ring out. They can leave a message" I said
"No answer it" Les demanded.
I looked at the phone. It was mum mums phone number. I answered.
"Hi Mum"
" Hi Jack, I left some washing in the machine. Are you at home? If so can you please hang it out?" she asked
Les was still in me. He knew it was my mother on the phone. He thrust into me again, and I shuddered and gasped at the surprise.
" Are you ok?" Mum asked. "You sound puffed" Les was giving it to me again as my mum asked the question. I composed and answered.
"Yeah mum, I was in the middle of doing push-ups" I said as Les slammed into me again. "I'm just laying on the bed" to cover up if she heard the bed squeak.
"Ok then. Your father is having a good day. He's backed a few good winners" Fuck it she wanted to talk more. I looked down at Les. He was enjoying this and was really pushing hard up into my ass.
" That's good mum. Mum I have to go I want to continue my workout" I said abruptly like any teenage boy would speak to his mother.
"Ok Jack. We'll see you tonight when we get home. Are you staying home tonight?"
"Yep that's the plan. See you later", I said cutting her off and hanging up.
Les was smirking evilly. " I wonder what mummy would have said if she knew what you were doing while she spike to you. Imagine if she knew that you had a big cock in your ass and were getting fucked hard while she spoke to you you naughty little girl."
"Ooh you're nasty, I like it" I said back to him with a grin.
I climbed off and turned from him putting my hands on the bed head pushing my ass towards him. He knelt up on the bed and moved in behind me and within moments forced himself back into me soon hammering away like a madman giving it to me real fast. I knew that he wouldn't be able to take this for long. He went for a few minutes and his breathing was very heavy. He would cum real soon and I didn't want him to yet. I pushed back with my hand to stop him.
"What's wrong?" he asked "Are you ok?"
"Yes I'm fine but you're about to cum and I don't want to finish yet but at the same time I don't want you to stop fucking me. I hopped off the bed and grabbed my bag of toys from the cupboard and poured them on the bed.
"Take your choice, use what you want" I said pretty much giving him an invitation to use whatever he wanted on me.
I laid on my side putting one leg in front of the other allowing him access to my ass. He grabbed my 10 inch dildo from the selection. It was pretty much his length but slightly fatter. I grabbed it from him and sucked on the tip slobbering it up. I then gave it back. He knelt on the bed behind me and I could feel him press the tip up against my ass. He pushed and my ass accepted it in. Gently he pushed the toy all the way into my ass. I looked at his face and he had a look of marvel as he watched the big toy go all the way up my loving ass. Soon he increased the pace of this push and was fucking me quite hard with the 10 inch toy. I loved it and he seemed to love giving it to me.
" I want more!" I demanded grabbing my massive 12inch toy from the selection. He looked at me amazed. It really was a big toy, apparently it was a direct replica of John Holmes cock (even though I have read on the internet that he only had a 10 - 11 inch cock) but none the less it was big.
Les put it up to my ass. He pushed, I opened and it was in. The look on his face was priceless. I had looked at it in the mirror before as I masturbated with it and it really did open my wide though it was nothing I could not comfortably handle. He started slowly fucking me with it, he pushed in as far as my body would allow it to go and pulled it all the way back out. Soon enough he was going quite fast and it was leaving me breathless. He kept going for what seemed an eternity as he continued to give it to me with monster toy. He then stopped.
" Jacki, I want you to give it to me" He said. He reached over and grabbed the much smaller 8 inch toy (pussy) and handed it to me. Ne knelt at the end of the bed resting on the bed head. It was the first time I had really looked at his ass. He was nice and clean and shaven, I'd presume he used cream on his balls and ass. I went for the lube and then changed my mind. I bent in towards his ass and started licking his balls from behind licking all around and working my way up towards his ass. I licked everywhere and made him nice and wet. He wasn't virgin tight as I could feel him open up as my tongue pushed on his hole. When I decided that he was wet enough and that I had had enough of this tongue lashing I placed the black dildo at his entrance. I gave it a little push and it slowly started to slide in. It looked nice as I pushed it a little deeper. I went deeper until it was right in. He took it pretty easily in the end. He doesn't need to be gentled I
thought as I pulled back and gave it a good thrust, followed by another and another. He moaned as I started to give him a good fucking from behind and I was soon pushing the toy hastily in and out of his ass. I got bored pretty son with this though. Lets test him I though as I slyly grabbed the 10 inch from next to me. I made a quick swap and pulled the 8 inch out and rapidly replaced it with the 10 inch. I didn't hesitate as I just forced it into him. I could feel his body tense as it pushed into his opening. I pushed it deeper and deeper and I could feel him gasp as it went all the way into his older ass. I let him adjust for a moment and then retracted the toy. I started fucking him slowly again and the pace increased gradually until I was soon giving it to him reasonably fast, pushing all 10 inches into him and back out again. He relaxed an was soon really enjoying it. I kept going for about 5 more minutes. It was really going in and out quite
easily now.
" Are you up for it?" I asked as I grabbed the 12 inch monster
"I'm not sure" he replied
" Come on baby" I encouraged " You can take it"
He silently agreed and turned back around. I pulled the 10 inch out of him and pushed the 12 inch to his loose hole. It was still wet and covered with my juices, I pushed it with some force as it halted at his opening at first. I pushed hard again and it popped in though the opening. He winced for a moment as I let it sit just inside of him. After a few moments I gave it a push and watched it push about 6 inches in. It looked fabulous watching this big cock stretch open the older mans sphincter. I pushed again and he had about 10 inches in him. It was getting hard to push now and I decided that he had reached his threshold. I pulled back and pushed it back in again and once again he moaned out aloud.
" how does it feel having a big 12inch cock up your ass Les?" I asked him
" It's so big Jacki!" he responded." I can feel it all the way in me"
" It feels great doesn't it Les, that's how it felt having your big cock in my ass, feeling you fill me up with your meat. I want you to fuck me again soon Les, but for now it's your turn to take the big cock"
I proceeded to fuck him again with reasonable pace, it was a big toy so I had to be more gentle as I pushed the latex cock in and out of his pipe. I gave him another 5 minutes or so and then decided that I wanted it again. I wasn't quite done with him yet though. I grabbed one of my butt plugs and replaced the cock with it. It was quite a wide butt plug, not quite as wide as the dildo but wide enough.
" Fuck me again Les" I demanded as I lay on my back pulling my knees up towards my chest. He was on top of me in no time and soon enough I could feel his lovely meat deep in me again. He really went at it fucking me real hard from above.
" Fuck me harder Les, come on fuck me harder" I demanded as he pushed his hips at me with great venom.
Soon he proclaimed " Fuck I'm going to cum Jacki!" He didn't have time to pull out as I felt his cum explode deep into my ass. It felt like a massive load as I could really feel it gushing up into my stomach. It was a pity that I didn't get to suck it all down my throat but maybe another time.
He collapsed on top of me. Cock still in me and butt plug still in him. He just lay there exhausted for a minute. He is older I guess so he's probably not in real good physical shape. I soon felt his cock soften and he fell out of me. He went to get up and told him to hold still as I pulled the butt plug from his ass.
" Jacki, you are a marvel. So much energy and enthusiasm. Makes it hard for an old man like me to keep up." He said
" You did just fine Les, in fact you did great. You felt great." I ensured him.
" Thank you Jacki"
We got cleaned up and soon said our goodbyes. I was hoping to see him again soon enough.
About a month went by and I had heard nothing from Les. Maybe he felt weird as he did work with my father after all.
One Wednesday evening my dad told me that our family was invited to a Sunday bbq at Les and Sarah's house. Dad asked if I wanted to come. I said yeah why not. Later that evening I got a text from Les.
" Your dad called , says you are coming to BBQ. Look forward to seeing you. Wear something nice : ) "
Sunday arrived. Obviously I couldn't wear something too nice to the BBQ but I slipped on a nice little red thong under my pants. We turned up at Les and Sarah's house and were greeted at the front door. It was just Mum, dad and myself. The BBQ was about an hour in. We had just eaten and I needed a pee. There was a toilet downstairs that was occupied. Sarah told me that I cold use the toilet in the bedroom ensuite upstairs if I needed to. I took up the offer and went upstairs. As I got up the stairs I could hear more footsteps coming up the stairs. I had hoped it was Les as I really hadn't even spoken to him yet since we arrived. Before going into the bathroom I saw him come into the bedroom. He quickly followed me into the bathroom.
"We have to be quick Jack" he said unzipping his trousers. I hopped straight down onto my knees in front of him and put his cock in my hand. I went straight at it sucking real hard and fast on his big hard cock. I kept sucking for a few minutes and then stood up. I dropped my pants revealing my thong. I turned and faced the mirror leaning over the bathroom counter. He grabbed some moisturising cream and rubbed it on my ass and his cock. It slid straight in. He fucked me like crazy furiously fucking away at my young ass. It didn't last very long when he said he was about to cum. I pushed him away quickly and dropped to my knees. I grabbed his cock and took it straight in my mouth. Sucking hard on it he instantly started to shoot load after load down my waiting throat. It tasted great and it was sure a big load. I sucked it all out and stood up. We checked that each other didn't get anything on us and we made our way back to the gathering.
Our arrangement was sure naughty and dangerous due to the circumstances. It didn't last long. I think we only fucked about 4 times in total but they were 4 good times. While I missed his big cock I wasn't short of options. Stay tuned for more.....