Educating Debbie
Debbie had been Keith and Angie's babysitter for about four years. Now eighteen, Keith had watched with admiration as she had developed into a beautiful young woman. In her final year at high school, Debbie was of medium height and slim with shoulder length dark brown hair. Keith had noted with interest Debbie's developing chest and although not large, Keith had occasionally caught glimpses of the outline of her pert breasts pushing against the flimsy material of her T shirt.
The best thing was that Keith got on really well with Debbie, conversation was easy and they were able to share a joke. He was sure that on occasions when Angie wasn't around, Debbie flirted with him and he had caught her checking him out when he was in his running gear. In his early thirties and still in great shape from Triathlons, Keith regarded himself as something of a favourite Uncle to Debbie.
Coming home early after a night out as Angie had a migraine, Keith sorted some tablets for her and saw her to bed. Grabbing his car keys, Debbie gathered her study books and followed him out to the car for the drive home.
They chatted easily as Keith drove and just as they approached a forest park, Debbie asked Keith to pull in.
'What's wrong' Keith spluttered, taken aback by the request.
'I just want to talk to you a minute' Debbie replied.
His mind in a whirl, Keith pulled into the car park, bringing the car to a halt in a secluded area.
'I want to ask you a personal question if that's ok?' Debbie asked.
'Sure' Keith laughed, 'we can talk freely.' He didn't expect however, what came next.
'Would you sleep with me?' Debbie asked.
'I'd love to Debbie, but what, why...' Keith struggled as his mind raced.
Debbie explained that she wanted to lose her virginity, but didn't want some guy her own age to just fuck her quickly and move on.
'I want it to be special, I want to know what to do and I don't now. I haven't been with anyone before and I would like you to be the one. You can teach me so that I know what to expect and do in the future.'
'You've been with some boys?' Keith questioned.
Debbie grimaced. 'Not with much success.' I tried to give one guy a blowjob, but he came straight away, covering my face and top. That was a disaster. I let another guy finger me. It hurt a bit and I got him to stop. I really need your help, please.'
Touched by Debbie's pleading and the look of concern on her face, Keith took a moment, and then said, 'Ok, I would be honoured to be the one, on one condition, no-one must ever find out.'
'Brilliant' exclaimed Debbie, her face lighting up. At the same time, Keith was thinking quickly about how to arrange things.
'Are you free Thursday morning?'
'Yes', Debbie replied excitedly. 'I have free study on Thursday mornings, I can easily get out of that.'
Keith arranged to pick Debbie up at 10.30 am in the shopping centre car park beside her school. Looking at the girl with a beaming smile on her face, he leaned over and kissed her softly on the lips. Debbie responded and Keith tentatively prised her lips apart with his tongue. Debbie met his tongue with her own and they engaged in a deep and satisfying kiss, their tongues entwining. Keith could feel his cock rock hard and straining at his pants. He placed a hand on Debbie's knee and slid it slowly upwards until he could massage her cunt through the crotch of her jeans. Taking her hand, he placed it on the lump in his pants and heard her sigh as she squeezed tightly.
Conscious of not going to far. Keith broke the embrace.
'Let's save it for Thursday' he laughed, and Debbie nodded in agreement.
After dropping Debbie off, Keith drove home, his mind racing at how he was going to manage things. The following day, he visited an out of town pharmacy, buying some condoms and lube. Every waking moment was focused on Thursday and the anticipation of enjoying Debbie's lithe body.
Finally, Thursday morning came. Keith dropped the kids off at school and Angie left for work as normal. Returning home, Keith went to the guest bedroom, pulling the blinds and placing the condoms and lube in a bedside drawer. He brought a towel in and placed it at the end of the bed, conscious of the fact that Debbie might bleed.
He was in the car park in good time. However, 10.30 came and went with no sign of Debbie. Feeling deflated, at 10.45 Keith was about to start the car when he spied her walking briskly towards him.
'Fuck' Debbie exclaimed as she sat in the passenger seat and explained that one of her Teachers had stopped her in the corridor as she was leaving, to talk over a forthcoming assignment.
'Don't worry' Keith replied relieved. 'Are you still up for this?'
'Definitely' Debbie replied laughing.
The drive to the house took around twenty minutes. As they drove, Keith cast an appreciative eye over Debbie, dressed in her maroon school blazer, grey skirt, which sat just above her knees, and grey ribbed tights. He found himself becoming hard in anticipation.
Keith was happy that no neighbours were about as they pulled into the drive. Opening the front door, he let Debbie in and locked it behind him. Keith directed Debbie to the guest bedroom. Once there, he turned her to face him and eased off her blazer, placing it on the bedside chair.
'You're still happy with this?' he asked.
'I haven't thought of much else' Debbie replied with a smile.
'If there's anything you're not happy with, tell me and we'll stop' Keith said, stroking the back of Debbie's neck, causing her to shiver, partly with nerves, and partly with anticipation. Keith leant in to kiss Debbie, softly at first and then with increasing vigour. Debbie responded and as she did, Keith ran his hands over her back, freeing her blouse from her skirt. Breaking the embrace, he undid her tie and threw it on top of the blazer. He resumed kissing her and at the same time began unbuttoning her blouse, kissing her neck as he did so.
Debbie was breathing heavily as her blouse was completely undone, giving Keith a view of her plain white bra. Keith's cock was straining the front of his pants at the thought of the beautiful breasts contained within.
Easing the blouse off one shoulder, Keith lightly kissed her neck and shoulder and at the same time ran a hand up her thighs cupping her pussy through her tights. Debbie gasped as Keith massaged her cunt, increasing the pressure and being rewarded with a low moan from Debbie. As he continued kissing her, Keith reached the waistband of her tights and pulled them down, leaving them mid-thigh. He then placed his hand on the front of her panties, noting with satisfaction a damp patch which he pressed on, causing Debbie to wiggle her hips at the pleasurable feelings coursing through her.
Keith undid his pants, pulling them partly down and took Debbie's hand placing it on his cock. She squeezed it eagerly through his boxers, before sliding a hand inside. The feel of her hand ringing his cock was superb and Keith encouraged her to slowly squeeze and stroke it.
As Debbie continued, Keith slid her blouse off her shoulders, throwing it on top of her blazer. He could see her nipples clearly causing little peaks in her bra. He resumed kissing her neck and upper chest and at the same time reached round and undid her bra - impressing himself at getting it right first time. Slowly he took the bra off, delighted when Debbie replaced her hand on his cock and continued massaging him. As he threw the bra on top of her other clothes, Keith got a first glimpse of her breasts. Smaller than Angie's, but beautifully formed and topped with small round pink nipples which stood erect and eager to be caressed.
Looking Debbie directly in the eye, Keith reached up and cupped one breast, stroking and circling it without touching the nipple. He alternated with the other breast, before running a finger around her right nipple and then squeezing it gently. He was rewarded with a sharp intake of breath from Debbie and immediately took the nipple in his mouth, rolling it with his tongue and gently biting on it. Debbie's response was to moan loudly and grip his cock harder.