The Education of Dennis

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 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.
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,’ 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 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 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!’