The Education of Dennis

Living 30kms north of Toronto afforded my wife, Jean and I the peace and tranquility of the country while remaining close to the amenities of the city. We're both 58 years of age and semi retired. Consulting work on a contract basis 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 on the inside and added an 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, a sex swing that disappears behind a sliding panel in the ceiling and two large sofas and chairs. French doors lead to a screened-off outside area similar to a lanai enabling us to make love beneath the stars. It's equipped with a 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. It's our outside oasis where we spend a lot of time during the warmer months; a place where we can relax, entertain and watch TV or listen to music via an audio/visual system that is built into a covered corner. The half-dozen couples we occasionally swing with and the two young black men Jean entertains once in a while find the area particularly conducive to sex.

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 scotch 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 Shirley and I had a good chat in the plunge pool while you and Carl played snooker.'

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

'Cocks,' she exclaimed.

'Not hens or chickens?' I quipped.

She ignored my attempt at not so subtle humour and continued.

'We were talking about Don's big one and how it feels inside us and I mentioned how much I like Tyrone's big black dick and it went from there to wondering just how big a cock we could take.' 'Did your combined wisdom reach a verdict?' I asked sarcastically. 'We didn't 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 as follows: East GTA/Durham 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. Have friends to share. Reply with details and photo of endowment and face.

She 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; 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 yielded nothing worthwhile but on the following Monday a response arrived that made Jean believe she had found "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. My penis was so much larger than my school pals and my shyness made the teasing very embarrassing for me 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 size and therefore have very little experience. 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 to teach me and 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. I live in Bingham so I'm near by. Sincerely Dennis

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. 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,' she said excitedly. The thought that he's 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.

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 turned 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 Horton's and after introductions, Jean sat down and I went to get the coffees. So far, so good I thought, at least he showed up.

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 a few seconds 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 warm to 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 levelled 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're 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. You loved my big hard dick and asked me to fuck you as you lay in the chair. I walked over, knelt in front of the chair and rubbed my erection over your pussy before entering you a little bit at a time until you couldn't take any more. Then fucked you until I pulled out and you jerked me until I shot all over your face. I actually printed the picture and covered it with cum.'

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're 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 think 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 had just finished his university term and had not yet found a summer job and was bunking temporarily with a friend. His time was very flexible. We said we would get back to him with a firm date.

Summer is a quiet business time for us and one of the reasons 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, mostly from home. 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 room and a job 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 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. I barbequed steaks for supper and the first lesson was to take place afterwards.

After showering we 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 make your lovely cock hard, don't be shy, if you want to jerk off....do it!'

Jean removed her robe to reveal a little red bustier that pushed her breasts up and forward, red stockings and spike heels completed her horny appearance. 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 hard cock in there?

Dennis stared intently and nodded, not moving a muscle, except for the one between his legs. It began to twitch as Jean turned, knelt into a chair and stuck her ass in the air. Her pussy was fully exposed and I could see her labia spread open in her excitement. She began playing with herself, fingers probing her pink wetness and rubbing her clit. Dennis' cock was now 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 your cock while I play with my pussy, its 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 ten seconds, spewing a stream of sperm into the air. Some almost hit Jean and she pumped her pussy violently and cried out in orgasm. His climax over, Dennis seemed to be suddenly aware of his cum that was splattered all over the tiled floor. 'I 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 his and kissed him on the lips. She took hold of his cock and walked him over to the wall of mirrors beside the bed and faced the glass. My wife knelt behind him and asked that he spread his feet a little. She caressed his balls with one hand and gently slid the other over the entire length of his hardening cock and tightened her grip a little, pulled the foreskin back and exposed his large knob. It was so thick she couldn't get her fingers around it so she used a spiralling 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 looked magnificent. Jean 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 soon caused her to squirm and emit sounds of pleasure as his tongue worked between her legs. After a while she asked him to stop saying it was time to put his cock inside her. Jean rubbed his cock along her pussy then gently pulled him in a few inches. She pulled him up 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 in and out, in and out.'

The lad moved up and down slowly, his shaft glistened with Jean's juices and each time he plunged into her my wife would groan with pleasure. He lasted little more than two minutes 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 has never been filled with so much cock before and it's because of you. 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 several days there was no shortage of lessons and Dennis was a willing pupil. They fucked two or three times a day and Dennis was beginning to gain control over his massive dick. Jean then set him a test. She masturbated him and squeezed down hard on the base of his penis telling him to concentrate and deny the urge to cum. For three days Dennis did not ejaculate under Jean's attentions and seemed to be growing in confidence. My wife admitted she was having lots of fun teaching this lad and was really turned on by his large dick. On the fourth day she began masturbating him, as usual, for several minutes then stopped and went over to the bed. She undressed and turned to Dennis, 'I want you to explore me,' she said and lay down.

He 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 making it easier for Dennis to explore her pussy and anus from behind. She turned onto her back again and instructed him to repeat the procedure but this time with his tongue. His cock was super hard and twitched frequently as he licked her pussy and clit.

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

Dennis lay on his back with his huge hard-on reaching almost to his chin. After a few jerks Jean leaned over 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, much later, it lay flaccid on his stomach.

'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 towelling 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 same lingerie and heels that Dennis had masturbated to in the photograph. Her legs were spread wide over the arms causing her pussy lips to part and expose her pink, wet vagina.

'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 as she spread her pussy wide with her fingers.

'The photograph,' he said, and stripped off quickly and approached my wife. His massive erection bobbed up and down as he walked. He knelt in front of her and rubbed his dick across her clit.

'Oh Dennis, put it in, fill me, fuck me hard, I want 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 pounded 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 got, thrusting her hips up to meet his cock.

I looked on in amazement as my wife took this huge penis inside her, she screamed and moaned with pleasure as it 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. Her orgasms were frequent and loud and she bucked her hips 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 lounged back the chair, 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 compete in the size department but my technique was more polished and Jean continued to orgasm as I filled her with sperm.

We showered and later, during dinner, gave our young handyman some news. Jean informed him that we had something special planned for 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. After lunch the surprise arrived in the form of our friends, Don and Carl and their wives Carol and Shirley. Dennis was shy at first but soon warmed to the attention of the ladies. The gals excused themselves and went upstairs and we four guys adjourned to extension.