Milked by Older men

Well I best introduce myself first. My name is Jason and the main story starts when I was 19, a fairly shy lad, just coming to terms with my sexuality. At 5’8”, smooth, slim build, a bubble butt and a nice 7” uncut cock I had got my first experiences in fumbled wank sessions at school. Then, when I was 17, I was asked to help move some boxes for an elderly neighbour in our village. Bill was probably in his 70’s, a widower, his wife having died earlier in the year. Bill had packed up his wife’s clothes and wanted them placed in the loft but didn’t feel confident on the ladder so it fell to me to lend a hand. 

“Right” Bill said “you get on the ladder and I can pass you the boxes”. 

As I climbed the ladder and received the first box I couldn’t help feeling Bill staring at me. I was a keen fell runner then and had donned my running kit ready for training later, my Lycra running pants and top with a hoody over. I suppose the pants did emphasise my pert bum and the outline of my cock as I climbed into the loft. As I climbed down for the next box Bill said, “be careful on that ladder, I don’t want you falling” and with that grasped my hips with his wiry hands. Up I went with the box, but as I climbed the rungs of the ladder I felt Bills hands slide down from my waist so they were resting on my bottom. I felt embarrassed but tried to just carry on. Down I came, next box and the same again but this time I could feel his hands rubbing my arse cheeks. Into the loft and I could see and feel my semi erect cock stirring in my pants, the Lycra only emphasising it. I tried to think of anything mundane to get my semi erect cock to behave but nothing worked. 

“Are you okay up there” Bill called. 

Nothing for it but down the ladder I came. As I came down Bill broke into a broad smile as his eyes dwelt on my bulge. 

“It’s awhile since I had the joy of an erect cock lad” he said. “At my age I don’t get an erection, certainly not since the wife died”. 

Bill talking about my cock had only made things worse as by now my cock was fully erect with precum showing through the Lycra. 

“I think you will need to see to that before we continue” Bill said as he ran his hand over my bulge. 

“Would you like me to give you a hand”, before I had a chance to answer he yanked my pants down and my cock sprang free.  On the landing, next to the ladder was an old stool, “sit there” Bill said. Doing as I was told Bill then proceeded to slowly wank me until I felt myself ready to burst. As my body started to go rigid ready for orgasm Bill quickened his wanking until my spunk was flying across the landing. 

“Right lad, that’s you taken care of, now clean yourself up and let’s finish those boxes”.

Nothing else was said and the situation never repeated though every time our paths crossed I am sure I blushed bright red, and also felt a stirring down below. Roll forward two years and having left 6th form with little work opportunity in the area I applied and was successful in getting a job with the Civil Service in London. After a couple of months I realised that living in London on a junior Civil Servants pay was going to be a struggle. I had managed to get a flat share with a another gay guy, around 4 years older than me which was good but I still struggled with my share of the rent. Greg, my flat mate, was aware I needed somewhere I could better afford and one day he said he may know someone who could offer a good lodging at a more reasonable rate. Greg worked at a well known gay bar in London which was the haunt of mainly older gay men. One of the bars older customers, Nigel, had mentioned in conversation that he was looking for a young man as a lodger and to help with some of the domestics. I was wary at first, wondering what the catch could be but Greg said he was a very nice, educated, old guy, about 80 who was lonely in his house in Chelsea since his partner died and found it hard to cope day to day. 

Well after sleeping on the idea I arranged with Greg that I would meet Nigel and make my decision then. That weekend Greg arranged for me to meet Nigel at the pub and so, that Sunday lunchtime I turned up as arranged and, having been introduced, Nigel suggested we take a seat in one of the booths to discuss if the proposal was acceptable to each of us. 

He certainly was a handsome old guy, about 6’ tall, slim with quite thick white hair. He was interested when I told him I was a Civil Servant as he explained that he had been a senior Civil servant before he retired. Well after a couple of drinks in the bar Nigel suggested I come back to his home to view the property and to see if I was interested. 

After a short taxi ride we arrived outside a beautiful old House, not far off the Kings Road. I couldn’t believe how splendid it looked as I walked through the front door. 

“Now” Nigel said “as you can see this is a spacious house and, whilst I have a lady who comes and cleans once a week I just find that at my age I could do with the odd bit of help now and again. Plus, I must admit, that since my partner died I do find it lonely here so to see a bright young face around the place would be a tonic for me.” 

Well after being shown what would be my bedroom which was the plushest bedroom I had ever seen I said “it’s such a lovely home but we haven’t discussed the rent, and I don’t see how I could ever afford this”. 

After a moments thought Nigel smiled and said “how does £50 a week sound. You will be doing me a favour and i feel that we will get on well.” 

That was it. An offer too good to refuse. We arranged I would move in the following weekend.

Over the next few weeks I settled in to a comfortable existence at Nigel’s. The jobs I helped with were nothing more than helping washing up, hoovering and dusting and similar domestic tasks. Nigel was the perfect gentleman, just like a second grandad. During this period I had hooked up with a guy in his 30’s who I stayed with most weekends. On my last weekend stopover we had argued and so I was wary how this weekend would proceed. The Friday evening seemed to go well but come Saturday evening we had a blazing row and I was thrown out. I headed to the bar to shed my sorrows to Greg, and after too many drinks went home to Chelsea. It wasn’t too late but knowing Nigel often went to bed early I quietly let myself in. 

“Thwack!” “Thwack” “Thwack”. 

It was coming from the doorway leading down to what I knew was the cellar, but somewhere that had always been kept locked. As I slowly walked through the open doorway and climbed down the stairs I was astounded to see a young guy in his early 20’s naked and stretched over what looked like an exercise horse and secured by his ankles and wrists at each leg. To one side was Clive, a friend of Nigel’s, who I had met once before when he visited with his wife. Clive was totally naked, and was wielding what looked like a table tennis bat “Thwack” on the lads arse. 

Clive must have been in his mid 70’s, and I knew from Nigel, he had been a very successful solicitor at Lincoln’s Inn. Clive seemed the opposite of Nigel, very portly compared to Nigel’s slim physique, about 5’9”, bald, with a large belly which, for all its size couldn’t hide a thick, rigid cock and the biggest, lowest hanging balls I had ever seen. As I tore my eyes away from Clive’s balls I noticed Nigel, sat naked on the floor between the lads legs greedily sucking his cock. As I was about to quickly turn around and leave Nigel caught sight of me. 

“Jason, I wasn’t expecting you back till tomorrow. You’ve stumbled on my little secret.” 

“I’m sorry” I muttered “Steve and I have split up and I’m feeling a little drunk, please forget I’m here, I will turn in.” 

“What you need Jason is to take your mind off what happened earlier. Young Luke here will see to that. Come and let him give you the best blow job you’ve had” said Clive. 

Now Luke was a very good looking lad, curly blond hair, a fabulous athletic body, big dick and super cute arse, my cock was already getting hard seeing Luke being used, though I wanted a one on one but where sex is concerned my cock rules. Stripping off I walked over to the front of Luke pushing my cock into his eager mouth. He sure was an expert cock sucker, Nigel had gone back to sucking his cock again and Clive, having put down the bat, started to lube up Luke’s arse, his finger slowly thrusting in and out, then, grasping Luke’s buttocks and spreading them wide he slowly thrust his fat cock into Luke’s young arse. The moans from Luke were muffled by my cock, and as Clive speeded up his thrusting, driving deeper into Luke I felt my dick ready to spurt, pulling out so I could cover Luke’s handsome face with my cum. By now Nigel had surfaced and I could see how fit he was for a man in his 80s and between his legs was a lovely cock which must have been 8” at least. He must have seen me eyeing him as he said “unfortunately although I still get an erection I no longer cum, but still get lots of pleasure.” I slumped back into an armchair as I watched Nigel take my place, cock in Luke’s beautiful mouth whilst he roughly squeezed Luke’s nipples. Sat there watching I thought how bizarre to think I’m here sharing a gorgeous young guy with two grandads! As I sat watching I could feel my cock rising again. 

“You ready for round two already” said Clive. “Come over and see what a sweet, tight hole this lad has.” 

Clive pulled out and I quickly took his place. Despite having been opened up by Clives thick penis Luke’s arse was a lovely, welcoming fit, warm, and nicely lubed. I was slowly fucking Luke, gyrating my hips to fully penetrate, whilst Nigel was inhaling poppers as he slowly fucked Luke’s mouth. 

“These really make me feel 21 again” Nigel said “as hard and horny as ever. Here,  please be my guest” as he passed the bottle over to me. The poppers certainly had the desired affect on me as I felt my dick swell to fill Luke’s tight hole. “Thwack”. Clive had started to spank my arse, and what at any other time I may have resisted with the affects of the poppers and the sensation of my fucking it seemed to add to what was the most amazing feeling. After about a dozen slaps I felt Clive’s hand gently massaging my arse cheeks then “Thwack” another half dozen, slightly harder slaps. 

“Ouch” I cried, “here, have some more poppers” Clive said. 

I took several big sniffs and then Clive leant forward to take the bottle off me. As he did so I could feel his semi erect cock push against my crack and his ample belly laying on top of my back. I heard Clive take a couple of deep sniffs of the poppers and then he started to massage my arse again. This time his fingers lightly played between my arse crack before I felt a moistness there and then a stubby finger sliding into my anus. Mmmmm, that felt good as I fucked Luke. His finger was going deeper, stimulating my perineum. As I continued to gyrate into Luke’s arse I suddenly realised that in place of his finger I now had Clive’s thick cock slowly pushing forward into my eager opening. This was so wrong, I thought, but it feels sooooo good. I pulled back from Luke, my arse stuck out to allow Clive full entry. Ooooooh yes! That felt good. I reentered Luke and had the double pleasure of giving and receiving , Clive’s balls slapping against me as he thrusted. Clive and I orgasmed at the same time whilst Nigel continued to face fuck Luke whilst pulling my nipples so that it enhanced all the other sensations. 

The next morning I woke up in my bedroom with my usual morning erection. Had I dreamed the sex of the night before. There was a gentle knock on the door and Nigel entered. “Good morning young man. I’ve brought you a cup of tea in case you wanted to have a lie in after last night”. “Thank you” I said “so I wasn’t dreaming it”. “You certainly were not Jason. Although you were slightly intoxicated you were very impressive during the evening”. “I remember fucking the young guy and then everything else seems a bit vague” I said. “Well after that you lay down on the bed I have in my cellar playroom and Luke dressed and went home. After letting him out I came back down to the cellar to find Clive just finishing giving you a blow job. He was very impressed with how quickly your cock recovered and what a lovely amount of sperm you produced. As you were still rather groggy from the alcohol Clive helped me bring you up to your bedroom. I had said goodnight to Clive and went to look in on you and you had thrown your sheets off and were laying here with the most wonderful erection so, dear boy, I took the liberty of taking my first taste of your cock before giving you a nice quick wank. I do hope this hasn’t made you feel uncomfortable and I will promise you that nothing similar will happen again, unless of course you wanted it to.” This last comment was said with a slight smile and a twinkle in the eye. “I must admit” I said “that when I first entered the cellar I was a little embarrassed to encounter two older men still having sex with a hot young guy but I did find it all highly erotic.” I went on to explain my encounter with Bill when I was 17 and that ever since then I had fantasised about older men taking advantage of me. If I hadn’t been so drunk last night I would probably have been too nervous for anything to happen but the sight of Luke restrained and being used gave me a huge turn on. “Well as you could see I have had an interest in bondage and when my partner was alive we had the cellar made into the playroom and we had regular play sessions there. Clive too, has a similar interest, although married. He regular picks up young men who are submissive and who we can play with. It’s all very tame really but everyone goes away satisfied. I must say that as he left, last night, Clive said he found you very attractive and wanted me to enquire if you would be up for further play.” I’m sure I blushed then, “oh, well I’m not sure. The thought of being restrained for sex does turn me on. Let me think about it and see if I have the courage for it.” “Let me know” Nigel said “there is no pressure to do anything but rest assured if you wanted to I will ensure all your limits are respected and all your fantasies fulfilled”. This last comment was said with a wink.

That week passed with work and I was out most evenings jogging so it was only at the next weekend that Nigel and I had much time together to talk. Nigel had let me have a look over the playroom cellar so I could become familiar with the equipment he had set up there, most of which I had no idea what it was or did. Nothing was said until that Sunday morning when, over breakfast, I turned to Nigel saying “I’ve been thinking all week about last weekend and the idea of being restrained. I would like to give it a go, if you promise me you will stop if I ask”. “Of course Jason. I’m so pleased you feel that way. Let’s arrange something for next weekend”.

That week seemed to fly by and all I could think of was what may lay in store for me come the weekend. That Thursday evening when I got home Nigel seemed very excited. “I think I have just the scenario for you for this weekend. I think it will satisfy your fantasies plus, knowing how quickly you recovered after cumming, I’m sure we will get multiple orgasms from you.” “Okay” I said, “so how will it work”. “Well let’s just say you will be in a position where your cock will be pleasured and pleasure from Sunday lunchtime till the evening.” With that he would say no more.

Friday and Saturday couldn’t go quick enough and by the time I awoke Sunday morning I had the hardest erection I think I had ever experienced. But I was also very nervous about what was to come. At midday Nigel summoned me down to the cellar where my introduction to restraints was to begin. “Right boy, strip off” Nigel ordered. He sounded so much more assertive than I had heard him before. I removed my polo shirt and jogging pants to reveal my rock hard erection. The anticipation was really working on my dick. Nigel cast his eyes over my smooth body as he came forward and gently stroked my cock. “Mmmm, I think you will make a lot of people very happy.” He said. He quickly attached leather wrist and ankle restraints to me and ordered me to lay on my back on the bed at one side of the cellar. Each restraint was then secured by a chain at each corner of the bed so that I lay, spreadeagled, my body fully exposed. Nigel stepped back to admire the sight before him and quickly stripped off himself before kneeling between my legs and gently running his tongue up my cock. As his tongue reached my cock head he licked the stream of precum into his mouth, with a moan of satisfaction. I too couldn’t help but moan as, by now, I was desperate to cum. Nigel took my cock, balls deep, into his mouth then proceeded to greedily suck me off, swallowing my cum. Wow, that felt so good. Nigel sat back, wanking himself, his cock looking so big and then he quickly moved up the bed, straddling my chest and pushing his cock into my mouth. I could taste the saltiness of him and what seemed an enormous amount of precum, but remembered that he had said he couldn’t manage to cum. That didn’t stop him from fucking my mouth for what seemed like an hour till he jerked forward with one enormous thrust of his cock. “Oh my, that was wonderful” he said. “Although I cannot cum I still get the sensation.” Now I think we should let the fun begin” he said with a slight leer. He then fetched what looked like a foot long stick with a clear silicon sheath, about 3” long, at one end. He then lubed up my semi flaccid dick and pushed the sleeve over it. I could feel a series of dimples and ridges as he worked my cock up through the sleeve, it getting slightly more erect as it went. Then a push of a button on the stick and I could feel an amazing vibration through the sleeve quickly bringing my cock back to full attention. The feeling was so intense on my still sensitive cock, but not enough to make me cum. Ohhhhh, that felt good. “Right my boy, I shall be back soon” Nigel said, and dressing, left me in the cellar.

I must of lay there for a good 15 minutes, my cock being kept hard by the wand vibrator, then, two men, both naked entered the cellar. The first was probably mid seventies, bespectacled, around 5’9” slim with the look of an ageing professor. As he approached the bed he was eagerly tugging on his limp dick. “Oh my, what a delightful boy for us to play with. I thought Nigel was joking when he said he had a young, cute lodger who wanted to meet older men.” The other man was similar height and build to the first, probably a couple of years younger but whereas the first man was very smooth this guy had a head of thick silver hair and a hairy, silver chest. He too was rapidly working on his cock to get himself hard. He strode over to the head of the bed and climbing up sat, straddled over my chest, pushing his, still limp dick in my mouth. “Suck on my cock boy” he said, as he leant back to grip my nipples. Meanwhile the first guy had moved to the bottom of the bed and, after removing the vibrator, had started to suck on my cock. As he did so, with my balls in his hand he gradually started to stretch them away from my body. The sensation, whilst being borderline uncomfortable had the effect of making my erection super hard. By now my sucking had had its desired affect and the second guys cock had grown and grown in my mouth till I was sucking on a very nice dick with a big bell end. “Change places” the first guy said and they swapped ends. Oh, was I surprised when guy number one leaned over me, with his cock in his hand. What had looked a limp, small dick when he entered the cellar was now about 9” long, still not fully hard but a real mouthful as I found as he gently fed the tip of into into my mouth. “Does that taste good lad.” He said. I had no chance to reply as it was eased into my mouth, his balls slapping against my chin. After a good few minutes of being face fucked and sucked the second man said “let’s see if the back side tastes as sweet as the front”. With that both guys climbed off the bed and unclipped my ankle restraints from the chains which had kept my legs spread to either side of the bed. One guy then took hold of my legs, pulling them back towards my shoulders where the other guy then attached the ankle restraints to the chains that were holding my arms outstretched. This had the effect of exposing my arse, slightly raised and cheeks spread. “Mmmmm” said the professor, “what an inviting site” before he grabbed hold of my cheeks, spreading them further before running his tongue along my crack. I could feel his tongue flicking along my hole over and over again whilst the other man held my legs, his cock in my mouth “suck it boy, suck it, drink my juice!” The professors tongue continued its flicking and I could feel my arse relaxing and twitching open, willing his tongue to delve into it. The professor willingly obliged and his tongue licked and poked into me then, moist and relaxed the tongue was replaced by a finger. Oh, that felt good rubbing my perineum. The professor had now one hand pleasuring my arse whilst his other was frantically wanking me. As the second guy shot his hot cum down my throat I exploded in a massive orgasm as the professors fingering became more rapid. As I lay back there, legs still up towards my shoulders and arse exposed the professor wanked off his big cock, emptying it’s hot load over my arse before rubbing his hot spunk into my arse. The two men then released my legs, reattaching the restraints at the bottom of the bed and putting my dick back into the vibrator sheath. This time the vibrations were turned up higher and, despite my cock having been drained twice within the space of less than an hour it was already getting erect with the sensation. After a short while Nigel came back and undid my restraints from the chains and removed the cock sheath vibrator. “Right Jason, you ready for round two” “I think so” I said, though my balls were already hanging a lot lower than normal after the cum that had already been extracted. “I have a friend who is bringing a special toy for you to enjoy” this was said with the biggest grin on Nigel’s face. I wondered what exactly I was letting myself in for. “Have you been in a sling before” “No” I replied, although I obviously knew what he meant and what that meant for me - my arse fully exposed. “Right Jason, I need you to give me a hand setting the sling up.” Nigel went over to a cupboard in the corner and took out the sling and in a matter of 10 minutes we had it set up. “Now in you get.” Said Nigel. After settling back in the sling Nigel fastened my ankle and wrist restraints to each corner of the sling so I was locked in. “It’s another quarter hour before our next guests arrive.” Nigel said “I think we should keep occupied until they arrive” with that Nigel knelt down between my legs and gave me the deepest, wettest rimming I’ve ever had. Next, with a small amount of lube he started fingering my hole until it was nicely open and fully lubed. “I think your ready now” and Nigel quickly left the room after first inserting a vibrator in my arse. After what seemed like forever but was in fact only about 15 minutes I heard voices descending the stairs. From my position in the sling I could get a good view of the doorway but I soon recognised Clive’s mellifluous tones and, as they came deeper into the room there were four other old men I guessed around the 70s and up age range. All were naked but, apart from one old guy with a large belly, all had stiff, erect cocks. Yes, viagra had a lot to answer for I thought. “Now then Jason, Gerald here” Nigel indicated the big bellied man with the soft cock “has a special treat for you, but first we need to put your ball gag in place.” I was on the verge of objecting but as I opened my mouth to speak the ball was between my teeth and fastened in seconds. Whilst the gag was going in I noticed Gerald moving to my side and placing a silver contraption on the floor with what looked like a pump next to it. He next hooked up some tubing from one of the hooks in the ceiling and proceeded to put my still erect cock into a plastic tube. “Now Jason I have been bragging to all my friends about my young friend with the always willing cock and how much you cum. Gerald wants to use his milking machine to see if I’m telling the truth and how much lovely juices he can milk from you.” With that Gerald switched on the machine and it started to work on my cock with a sucking motion drawing my foreskin up over my cockhead with a slurping sound ever couple of seconds. It felt so good. Nigel came round to my head and held a bottle of poppers under each nostril in turn allowing me to inhale deeply whilst at the same time I felt the vibrator being removed from my arse to be replaced by one of the old guys cocks. I could feel the guys cock enter me and as he started his slow deep thrusting I could feel it swelling and filling my arse. Oh that felt so good, the rythmn of the swing as the thrusts grew faster and the slurping of the milking machine as it continued its relentless sucking. All this time I had hands stroking all over my body, cupping and teasing my balls, pulling or sucking my nipples whilst each old guy took turns kissing me. After 5 or 10 minutes they would change positions, each one taking turns fucking me. I got to tell which of them had entered me after awhile by the size of their cocks but more by the way they fucked. By now I had cum twice more and my cock was struggling to keep pace. Gerald was skilful in ensuring the milking tube was kept lubricated but, realising a different approach was needed he removed the milker and very gently and slowly started to wank me. After around 15 minutes of gentle manipulation, and another dose of poppers, Gerald said “it looks like your ready to deliver some more” and the milker was put back in place. Twice more I came, once a dribble and one dry orgasm.  By now I had spunk in my arse and those that didn’t fill me there provided me with a lovely cum shower.

That very special day turned into one of many and, through recommendations, led to many invitations to visit senior friends.