The Education of Dennis

Author: talon

Living 30kms north of Toronto afforded my wife, Jean and I the peace and quiet of the country while still being close to the city. We are both 58 years old and semi retired, doing consulting work on a contract basis, which leaves us lots of free time to indulge our many interests.

Our home is a 110 year old farm house that we have completely renovated inside and built a huge extension onto the back. Our nearest neighbours are 4kms away so we have total privacy – one of the reasons we purchased the home. The extension was built to satisfy our love of sex and has a small hot tub, a king-size bed with mirrors above and to one side, sex swing that disappears behind a sliding panel in the ceiling, two large sofas and chairs, and an adjustable table with a soft, cushioned top. French doors lead to a screened- off outside area similar to a lanai with a retractable solid-to-mesh roof so we can make love beneath the stars while avoiding mosquito bites, large hot tub, several built-in lounging decks covered with thick padding at various heights allowing for many different sexual positions, a small plunge pool with waterfall and lots of plantings both inside and outside the screen that complete the area. It is our outside oasis where we spend a lot of time during the warmer months; a place where we can relax, entertain our friends, watch TV or listen to music via an audio/visual system that is built into a gunnited rock wall. The half-dozen couples we occasionally swing with and the four young men Jean entertains once in a while find the area particularly enjoyable.

It was Wednesday evening, we’d had a quiet day around the house and were lolling in the small hot tub, Jean sipping on a glass of wine and I was on my third Guinness when my wife broke the silence. ‘Evan, remember last weekend when Carl and Shirley were here, well, after you guys had your way with us Shirl and I had a good chat in the plunge pool while you and Carl played snooker.’

‘As I remember, it was you and Shirl who had your wicked way with us poor guys, still never mind, what did you talk about?’ I responded.

‘Cocks! Just cocks!’ she said.

‘Not hens or chickens, just cocks?’ I mused.

She ignored my attempt at subtle humour and continued, ‘Well, we were talking about Don’s big one and how it feels and I mentioned how much I liked my four big black ones and it went from there to wondering how big a cock can be.’

‘And your combined wisdom reached what verdict?’ I asked sarcastically.

‘We didn’t reach one but I’ve been thinking I’d like to find out.’

‘How will you do that,’ I said, becoming a little more interested in where this conversation was going.

‘By putting a posting on the swinger website we use,’ she answered.

‘And when you find this giant dick what will you do with it?’

‘I’m not sure but it might be fun finding out,’ she said with a smile.

‘It might at that,’ I said. ‘I guess there’s no harm in checking it out.’

‘Oh good!’ exclaimed my wife jumping out of the tub and heading for the computer.

The posting read:                Married woman, 58, slim blonde, very sensual, enjoys dressing up in lingerie, stockings and heels seeks extremely well endowed male for    erotic fun. Husband will be present at all times and may watch and/or participate. Only educated, clean, sincere men need respond. Reply with details and photo of body and face.

Jean attached two nude photos of herself then posted the profile, there was nothing left to do now but wait and see.

The rest of the week was busy and we didn’t check for replies until Sunday. There were fourteen responses; six were obvious phonies or idiots, three lived too far away and the remaining five professed to have endowment to 9”. Our friend Don has 9½” so these replies were non-starters. Jean was a little disappointed but understood it may take some time to find “IT” as we had come to describe the search.

The next two weeks were no better but on the following Monday a response arrived that made Jean believe that maybe, just maybe, it was “IT”. I arrived home late and Jean was very excited and read the response to me immediately….. Hello, my name is Dennis and I am 19 years old. I noticed at an early age that I was different from other boys for my penis was so much larger than my schoolmates and my shyness made the teasing very embarrassing and to avoid this I tended to spend a lot of time on my own. As I grew older I experienced problems with girls because of my large endowment and therefore have very little experience. I recently moved into my own apartment but my male friends constantly harp about my penis and all the girls I’ve met seem afraid of it and treat me as a freak. I must confess that I am a virgin, one girl did fondle me but I ejaculated almost immediately onto her dress and she became very angry. I thought perhaps an older, experienced lady is what I should be looking for so when I saw your profile I decided to write to you. You look very sexy, and I masturbated while looking at your pictures. I guess you may be seeking a more confident, experienced man but I thought I would try. I need to learn how to enjoy and give enjoyment to a woman. Sorry, I don’t have a photo of my endowment but it is big – 17” and thick.         

Jean looked at me, willing me to answer, ‘Ah, poor kid, only 17 inches – if it’s the truth, what makes you think it is?’ I said.

‘His reply just seems genuine to me, no bragging or stupid claims like so many idiots that waste their time and ours on the swinger site,’ replied Jean seriously. ‘Let’s find out, he only lives twenty minutes away and if he is for real……17 inches, that’s hard to believe, but very interesting.’

‘Ah, so it is the cock, I was beginning to think it was the mother hen clucking.’

‘Shut up! Anyway, the thought that he is a virgin is rather exciting, I fancy teaching him how to use his gift and I am a good teacher – I taught you everything you know about sex after all.’

Jean sent an e-mail to Dennis suggesting a meeting at a coffee shop near his apartment and he responded within an hour. Thursday evening was agreed to and Jean was noticeably excited, as, I’m sure, was young Dennis. ‘Hey, don’t count your chickens before you see the cock’ I joked and was told to shut up yet again.

I must admit to being interested; since we began swinging a few years ago I discovered that watching my wife being fucked by other men really turns me on and if this guy was indeed genuine I wanted to see her with his cock.

We recognized Dennis sitting in a quiet corner of the Tim Hortons and after introductions, Jean sat down and I went to get the coffees. ‘So far, so good’ I thought, ‘at least he showed up.’

After chatting for a few minutes about the weather and the Leafs just to break the ice it was obvious that Dennis was very nervous, he would look at Jean for several seconds at a time but was reluctant to look me in the eye. Despite this he did have a sincere air about him and was very polite, I was beginning to like him. Perhaps Jean was right after all – feminine intuition and all that.

I decided to cut to the chase, my coffee was almost gone and I was tired, ‘Dennis, when you masturbated while looking at the pictures of Jean, what were you thinking about?’

He hesitated for a moment, looked into his cup then leveled a stare at me and replied, ‘Can I tell exactly what I thought?’

Jean cut in before I could reply; she always was faster with the tongue than me, in more ways than one. ‘Please Dennis; don’t hold back, we are not shy.’

‘You looked so sexy in the picture….the one where you were wearing that garter belt with stockings and high heels. Lying back in the chair with your legs spread so wide, well, I imagined you were like that for me and you wanted me. I imagined I was a good lover and that you loved my big dick and asked me to fuck you as you lay in the chair. I walk over, kneel in front of the chair and rub my erection over your pussy before entering you a little bit at a time until you can’t take any more inside, then I then I fuck you until I pull out and you wank me until I come all over your face.’

He looked down, a little embarrassed, Jean smiled but for once I was first to reply, ‘Dennis, that photo makes all the guys who have seen it think that way, even me, so don’t think you are different and there’s no need to feel embarrassed. I’m sure Jean would enjoy making your fantasy a reality.’

‘Would you like to join us sometime and see how we get along?’ Jean blurted.

‘I would like that very much’ the lad said.

He shifted uncomfortably on his chair and I saw the massive bulge in his crotch. Jean noticed it also and shot me a self satisfied smirk. I couldn’t help wondering if he had just ejaculated in his pants.

He told us his schedule was open since he off university and had not yet found a job for the summer, we said we would get back to him with a firm date.

Summer is a quiet business time for us and one reason we invested so much in our outdoor extension. Jean had no consulting until September and I was working the equivalent of a day and a half a week. Since we would be at home the majority of the summer an idea sprang to mind that I thought may make the time more interesting.

‘Jean, there’s an awful lot of work to do around here, I was thinking of hiring a handyman. Someone to keep the garden in decent shape and do minor repairs about the old homestead.’

‘Have anyone in mind?’ she replied absently.

‘I know a guy named Dennis who is looking for a job and more besides.’

My wife almost dislocated her neck turning to look my way. ‘You dog, what are you thinking?’

We have lots of space; offer Dennis a job and a room for the summer. You will have lots of time to teach and in his spare time, if he still has any energy left, he can do odd jobs.

‘I know now why I love you so much, call him,’ she said with a grin.

Dennis moved in on Sunday afternoon with much unnecessary fussing from Jean while giving him the Grand Tour. I barbequed shrimp for supper and the first lesson was to take place afterwards.

Following supper we all adjourned for a shower and met in the extension dressed in bathrobes. Jean wore one of mine that touched to floor because she had a little surprise underneath. Dennis was so nervous I couldn’t detect any bulge or movement beneath his robe. Hope he is able to get it up after all this, I thought, I want to see his prick almost as much as Jean.

I slumped into a chair and watched as Jean began the lesson. They were standing facing each other about six feet apart, ‘Now Dennis, I want you to know that this will take time and it’s okay if things don’t go as you plan in your mind.’ She drew a deep breath and continued, ‘Take off your robe.’ He stood naked before Jean and his cock was indeed impressive. His soft penis dangled between his legs and was at least a foot long and looked heavy, Jean’s eyes widened with either disbelief or delight, or perhaps both. ‘I’m going to help you make your lovely cock hard, don’t be shy, if you want to wank….do it!’
Jean removed her robe to reveal a little red bustiere that pushed her breasts up and forward, matching stockings and spike heels. She fondled her tits and played with her pussy while talking to Dennis. “You want to feel my tits and kiss them don’t you Dennis? My pussy is all wet just looking at your big, beautiful dick, would you like to eat my pussy and put your dick in there?
Dennis stared intently and nodded, not moving a muscle, except for the one between his legs. It began to move ever so slightly as Jean turned, knelt into a chair with her ass in the air and with her open pussy lips in full view, began playing with herself. My cock was hard and as I glanced from Jean to Dennis I saw it was affecting him also. His cock was hard and sticking out horizontally, every couple of seconds it would twitch violently upwards. Jean turned and sat in the chair, draped her legs over the arms and said, ’Dennis, play with you cock while I play with my pussy, it’s okay if you cum, I’ve cum two or three times already just looking at you and I will help you cum again and again.’

Dennis grabbed his giant member and stroked it wildly and came in about five seconds. A stream of sperm shot out and almost hit Jean who caught her breath sharply as it happened. His climax over, Dennis seemed to be suddenly aware of his cum all over the tiled floor. ‘I’m sorry, I’m sorry’ he blurted, looking a little desperate and not sure what to do.

It’s alright’ said Jean leaning over to the table beside the chair, she grabbed a towel and quickly cleaned up.

She approached Dennis, pressed her body against him and kissed him on the lips. Taking hold of his cock, she walked him over to the wall of mirrors beside the bed and facing the glass; she knelt behind him and asked that he spread his feet a little. She caressed his balls with one hand while gently sliding the other over the entire length of his hardening cock, tightening her grip a little around the head, pulling the foreskin back to expose the large head. It was so thick she couldn’t get her fingers around it so she used a spiral motion as she moved up and down his huge erection.

‘Look at your beautiful big cock, Dennis; it’s becoming nice and hard for me again. Do you want to put it in my wet, slippery pussy?’

Dennis managed only a nod. His erection was now full and it certainly was magnificent. Jean rose, lay on the bed and opened her legs wide. ‘Come and eat me’ she said and Dennis obeyed. ‘Feel my breasts and nipples, she continued.
Dennis was a rapid learner and Jean an excellent teacher. With Jean’s direction he was soon causing her to squirm and emit sounds of pleasure as he tongued between her legs. After a while she asked him to stop saying it was time to put his cock inside her. With Dennis in front of her Jean rubbed his cock along her pussy then gently pulled him in a few inches. She urged Dennis over her and lifted her knees as far back as she could.

As Dennis braced himself over my wife there was still a massive amount of cock between his balls and Jean’s pussy and I wondered just how much of it she could take.

Slowly, she pulled more cock into her until about four inches remained, Oh yes, she moaned, ‘Now Dennis, in and out, in and out.’

The lad moved up and down, lifting his ass high in the air exposing his shaft that glistened with Jean’s juices before plunging it back in at which point my wife would groan with pleasure. He lasted less than a minute and I watched as his sperm overflowed Jean’s pussy and ran down to her ass.

‘Ah, no,’ Dennis muttered as he slumped over Jean.

‘It’s alright, that was lovely and you were very good, my pussy is so wet and it’s because of what you did. We’ve only just started, you will be able to last much longer, believe me,’ Jean comforted as she stroked the back of his head.

Over the next few days there was no shortage of lessons and Dennis was a willing pupil. Jean would masturbate him and squeeze down hard on the base of his penis telling him to concentrate and try and control the urge to cum. For three days Dennis did not ejaculate and seemed to be growing in confidence. Jean admitted that she was having lots of fun teaching this lad and was really turned on by his large dick.

Jean had wanked Dennis for several minutes, his cock, as usual, was rock hard. She had not allowed him to touch her since the first night wanting him to gain some control but now she removed her clothes and went over to the bed. ‘Dennis, I want you to explore me,’ she said and lay down.

Dennis knelt beside her and began to caress her feet and legs, moving over her tummy and then to her breasts. He moved his hands down to her pussy, caressing the mound of blonde hair before parting her lips and inserting three fingers. Jean moaned as he screwed her with his fingers and pinched her clit then she rolled over and he caressed her back, buttocks and legs before returning to her bottom. Jean raised her ass in the air a little making it easier for Dennis to explore her pussy and anus from behind.

Jean turned onto her back again and instructed Dennis to repeat the procedure but with his tongue this time. His cock was super hard and twitched whenever Jean moaned as he licked her pussy.

‘You’ve done very well,’ said Jean sitting on the bed. ‘I do believe you need a reward, lie down.’

Dennis lay on his back with his huge hard-on reaching almost to his chin. After a few jerks, Jean took him into her mouth and gave him a wonderful blow job. He lasted for several minutes before shooting a massive load of cum into Jean’s mouth which she let fall all over his erect shaft. She continued to play with his cock until he was soft.

‘More lessons tomorrow afternoon, now off you go to work, the pool needs a clean and Evan has a few errands for you to run,’ Jean said after toweling cum from her chin and Dennis’ cock.

It was arranged that Dennis would meet Jean at three o’clock in the extension. When he arrived my wife was laying back in one of our oversized leather chairs wearing the lingerie and heels Dennis had masturbated to in the photograph. Her legs were spread wide over the arms causing her pussy lips to part slightly.

‘I’m here like this for you, take off your clothes and come here, I want you to fill me with your beautiful big cock,’ Jean said to Dennis as she spread her pussy open further with her fingers.

‘The photograph,’ he said, stripped off quickly and approached my wife, his massive erection sticking straight out and bobbing up and down as he walked. He knelt in front of her and rubbed his dick across her clit.

‘Oh Dennis, put it in, fuck me hard, I want and need your cock inside me,’ moaned Jean.

Dennis adjusted his position over Jean and pushed his big, thick cock into her and began long thrusts in and out. At least twelve inches of hard dick was pounding my wife and I could see by the ease with which it went in and the shine on it that she was very aroused. He held her ass in his hands as he screwed into her, pulling her onto him until he was almost up to his nuts inside her. Jean was giving as good as she was getting, thrusting her hips up to meet his cock.

I looked on in amazement as my wife enjoyed all of this huge penis inside her, she screamed and moaned with pleasure as he filled her. She had taught him well, he fucked her hard and fast for several minutes then slowed and moved the entire length of his erection in and out her gaping pussy. When he pulled out I saw her pussy stretched wide open ready for the next onslaught of cock. Her orgasms were frequent and loud and her hips bucked wildly. Dennis began to increase speed until his strokes became shorter and I knew he was getting close. He moaned and Jean screamed as he pulled his cock out, Jean took hold of it and jerked vigorously until he came with several spurts onto her face. She sucked him clean and with a somewhat exhausted smile declared, ‘Test passed, Grade A, Dennis my love, that was incredible….YOU are incredible!’

‘It’s all because of you Jean, if anyone is incredible it’s YOU!’ Dennis responded.

‘Well done Dennis,’ I congratulated, ‘that sure was a good performance, I’ve never known Jean to cum like that and sure as hell I’ve never seen her so full of cock.’

Jean was lounging back the chair with her legs once again spread over the arms, her pussy looked so inviting I couldn’t resist, ‘You look like you need more cock,’ I said as I shed my clothes. I slid into her wet pussy and showed the kid how it was done. I couldn’t win in the size department but my technique was more polished and Jean continued to orgasm as I filled her with sperm.

We showered and during dinner gave our young guest some news. Jean informed him that we had a surprise for him on Sunday afternoon. He was not to ejaculate in the meantime since it would spoil the surprise.

We kept Dennis busy with chores, hoping to occupy his mind with something other than sex, until Sunday afternoon. The doorbell rang as we sat at the kitchen table following lunch and I greeted our friends Don, Carol, Carl and Shirl.
I introduced them to Dennis who acted a little shy at first but soon warmed to the attention of the ladies. The three girls excused themselves to go upstairs and Jean said that since it was such a lovely they would meet us in the ‘outdoor playroom.’

‘So, you have been studying under Jean or rather on top of Jean I hear,’ said Carl jokingly.

David nodded and smiled and the four of us chatted about his ‘education’. He told us how much he had learned from Jean and how he felt much more confident with women and about his unusual endowment. His preference for mature woman had only increased during the time he had spent with us and he hoped he could see Jean again after he left and intended to date only mature, sexually confident, women in the future.

We had another beer while watching the game and chatted idly about everything and nothing but always coming back to sex as guys tend to do until the girls joined us. They strode into the room wearing stilettos, stockings and half-cup bras.

The girls stood in a line before us and fondled their tits and pussies before they turned around, bent over with legs spread and gave us very horny rear views. They stood and faced us again and Jean spoke, ‘Okay guys, get rid of your clothes, not you Dennis…you come here.’

Dennis joined the girls as we stripped and he was feeling them as they groped and undressed him. There were cries of disbelief from Carol and Shirl when Dennis’ cock was sprung free and they explored every inch of it with their hands before all three went down on their knees and did the same with their tongues and mouths. Carl, Don and I sat and played with ourselves as we watched our wives with Dennis. The girls went over to the bed and lay down side by side and Dennis went to each fingering, licking and eating pussy and mauling tits.

‘I have to feel that dick inside me’ Shirl stated and pushed the button that released the sex-swing. The ceiling panel opened and down it came and Shirl clambered into it. ‘Come here love,’ she said to Dennis, ‘Jean, line me up please will you?’

Jean pressed the switch that adjusted the height of the swing until Shirl’s pussy lined up perfectly with Dennis’ cock. Carol and Jean stood beside Dennis and played with his cock while he fingered Shirl. Carl came over to take a closer look as his wife was about to be fucked by the biggest dick that had ever entered her pussy.

Carl was wanking when he said, ‘She’s so wet and ready, stick that prick into her, she wants it bad.’ Dennis moved his cock to Shirl’s pussy and Carol and Jean moved it up and down along her lips.

‘Oh, give it to me, give it to me!’ she panted and the huge penis began its journey. Shirl caught her breath several times as the cock descended into her and Carl put his hard dick into her mouth.

Carol motioned for Don and me to join them and she wanked me while Jean wanked Don and we all watched Dennis laying his massive pipe into Shirl. Now Shirl has always been very vocal during sex but she was downright ear-splitting as the cock rammed into her again and again and she seemed to come each time it was all the way in. Dennis was in control and showed no signs of nearing ejaculation as he gave Shirl a real workout.

‘Let me try.’ Carol said excitedly and Dennis withdrew slowly to reveal a pussy that had been well and truly fucked. Shirl staggered out of the swing and Carol climbed in. Dennis fucked Carol in the manner while she sucked me, Jean sucked Carl and Shirl sucked Don’s 9½” that somehow looked smaller now. When Dennis withdrew several minutes later Carol too knew she had been royally screwed. ‘Wow, that was great, what a cock!’ she exclaimed and she dismounted from the swing and walked a little unsteadily over to the bed.

We all made our way to the bed and Don, Carl and I lay down on our backs. The girls got on all four at the edge of the bed and began oral sex, Jean with Don, Carol with Carl and Shirl with me. Dennis stood behind and fondled them before inserting his penis into each of them. As he fucked one he fingered another and when Jean, who was in the middle, was receiving his meat he finger fucked the other two. Don was first to cum followed by me and then Carl, Dennis was still going strong, however, his cock sliding into one pussy after another every few minutes.

‘I’m cumming,’ yelled Dennis and the girls turned to receive his load. All three faces were inches away from his cock as he jerked it to a violent eruption, spraying sperm into all three open mouths.

Everyone cleaned up, I made a supper of baked salmon and we enjoyed the meal in our outside play area naked. With the dishes out of the way, we relaxed with coffee and liqueur on the padded lounging decks and enjoyed the early evening sunshine. Carol was lying on her side directly opposite Dennis and I watched as she teased him by slowly, almost absent-mindedly, tracing a finger from her neck, to her nipples, down across her tummy to her pussy where she would gently play with her clit before reversing the path back to her neck. I glanced at Dennis and saw it was having an effect and thought to myself that Carol was going to get fucked again. I had sensed earlier that Dennis was partial to Carol; she is 5’ 11” tall with a statuesque body, large tits with big nipples and an oversized clitoris, when she was being fucked I noticed that Dennis had no trouble driving the entire length of his erection into her and he fucked her much harder and deeper than Jean or Shirl. She lay onto her back and curled a subtle finger for Dennis to come. He walked across to her, his cock already beginning to rise, and climbed on top of her. She took hold of his semi-hard dick and stuffed it into her.

‘I want to see this up close,’ I said and went over and sat at the end of the deck they were on and sat on the floor. I was at eye level with their bodies about a foot away from Carol’s pussy as that big penis, now as hard as granite, drove into her. Dennis was withdrawing at least twelve inches and as he came down I could see Carol’s clit being pushed down into her pussy by the thickness of the cock. The sensation must have been tremendous, she was creaming all over his dick and it was running down to her anus, her moans were moans of sheer pleasure. Shirl joined me and after stroking me for a while climbed on top and sat down on my cock. I glanced over and Jean was being fucked by Carl as she sucked on Dons erection.

‘This has certainly been an interesting couple of weeks, I wonder what next week will bring? Dennis has certainly got an education and Jean has loved the teaching. Carol has finally found someone bigger than Don to fill her hungry pussy, Shirl has also experienced the biggest cock of her life but seems quite content bouncing up and down on my average endowment and Carl and Don….well they seem to enjoy fucking my wife more than there own wives and me….I enjoy watching Jean get fucked and I think she was more interested in teaching Dennis how to use his oversized penis than she was the actual size of it.
Shirl is moaning and bouncing faster on top of me, I grab her ass with both hands and pull her down harder and ejaculate….Dennis is grunting and Carol screams as he fills her with cum….I turn my head to see Jean on her hands and knees with Don fucking her from behind and Carl fucking her mouth. Carl squirts onto Jean’s face and Don cums inside her a couple of minutes later.

Ah well, I muse, just another quiet weekend in the country.

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