educating-debbie
FIRST TIME SEX STORIES

Educating Debbie

Educating Debbie

by slinwet95
19 min read
4.46 (32299 views)
adultfiction

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.

📖 Related First Time Sex Stories Magazines

Explore premium magazines in this category

View All →

'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.

Alternating between Debbie's breasts, Keith decided to progress things further. Standing, he manoeuvred Debbie into a sitting position on the bed and gently pushed her unto her back, her feet still on the floor. Kneeling, he took off her shoes and pulled her tights off in one movement. The damp patch on the front of her panties had grown larger. With increased excitement, Keith stepped out of his trousers and pulled off his boxers, giving Debbie full view of his fully erect uncut cock which stood proud against his belly.

Kneeling again, Keith pushed Debbie's legs wider and beginning at her feet, planted small kisses on each leg all the way up to her inner thighs, avoiding touching her panties. He then licked her inner thighs, savouring the heat and scent emanating from her pussy. By this time, the front of Debbie's panties were soaked. Reaching out his tongue, Keith licked the length of her slit through her panties causing Debbie to moan softly. Placing his thumbs in each side of the waistband, Keith slowly pulled the panties down, marvelling at the sight of a neat triangle of dark brown hair, glistening, and bisected by a pair of slightly open pink lips.

In a state of increased excitement, Keith placed Debbie's legs over his shoulders and bending his head extended his tongue to touch the distended lips. Debbie jumped at the first touch. Breathing heavily, she gripped the duvet with both hands as Keith licked the length of her pussy, accurately locating the little nub of her clitoris. Debbie jumped at this and as Keith focused on it, licking around it and pressuring it with his tongue, Debbie began to writhe on the bed, forcing her cunt into Keith's face. As Keith increased the pressure, it was moments before Debbie came with a loud cry, raising her head and shoulders off the bed, before collapsing, breathing heavily.

'Did you enjoy that?' Keith laughed.

'It was wonderful' Debbie replied. 'I didn't know it could be so good.'

'We've only started,' Keith said, and pulling Debbie to her feet, kissed her and whispered, 'suck my cock.'

Debbie immediately knelt and taking hold of his balls with one hand, she ringed his cock with the other, slowly massaging up and down. With his foreskin fully retracted, a small bead of pre cum had formed and Keith watched captivated as Debbie bent her head and took the glans in her mouth. Keith massaged her head as she moved her head up and down, taking in more of his shaft with each movement. The feather light touch of her tongue round his glans was exquisite and Keith was delighted when she gripped both his buttocks and used her mouth to take his full length to the back of her throat. Keith could feel a climax approaching and he knew that he had to stop her before he came.

'Whoa!' he exclaimed laughing. Reaching down and lifting Debbie to her feet. He kissed her deeply, their juices mingling.

'That was brilliant Debbie, you have no problems in that department' Keith said. Moving Debbie into a lying position on the bed, Keith lay alongside her, the two kissing and caressing each other. Caressing Debbie's hips, Keith slowly slid his hand down and between her thighs. Debbie shifted on the bed to accommodate him and as she did so, Keith ran his middle finger the length of her well lubricated slit before gently inserting the tip. Her pussy was tight on his finger and as Keith inserted it further, Debbie gripped his cock and began to slowly pump it. As he withdrew his finger, Keith tried to insert two fingers. This caused Debbie some discomfort, so he withdrew. Realising that Debbie was quite tight, Keith decided to let her take control. Rolling onto his side, he took a condom from the drawer and ripping open the packet with his teeth, rolled it down over his erect penis. Taking the lubricant, he squeezed a generous amount onto his hand and massaged it into Debbie's pussy, sliding his finger in and out a few times.

Lying on his back, he got Debbie to straddle him.

'Debbie, I want you to manage this. You decide how much you want to take and how quickly.' Debbie nodded in assent, and taking Keith's cock in her hand, slid it along her lips until it was against her opening. Pushing her body down slowly, Debbie winced as the head of Keith's cock began to stretch her. At the same time, Keith caressed her hips and back and then played with her breasts, gently squeezing her swollen nipples. Debbie was breathing heavily as she pushed slowly, taking more of Keith's cock into her. Keith was amazed at how tight her pussy was and was thrilled at the grip of her muscles on his cock. Debbie emitted a low moan as she sank the last couple of inches in one go, ensuring the cock was completely embedded within her. After a few seconds Debbie began to move her hips, grinding the cock deeply into her. She bit her lip as she increased her pace and Keith felt the excitement rising within him. Pulling her forward onto his chest, Keith thrust upwards with his hips forcing his cock in and out of her tight cunt. Debbie began to moan with increasing rapidity and forcing her hips into Keith, came with a long, low groan.

'Oooh, that was beautiful' Debbie said smiling when she caught her breath.

'Glad to be of service' Keith laughed, rolling on the bed, still embedded within Debbie, so that he was on top of her. Slowly, he began to fuck her, lifting her thighs and wrapping her legs around his waist. He pushed his cock in to its full length, before withdrawing it slowly and completely. As he repeated this he was delighted to see Debbie thrusting her hips upwards and pulling him into her with her legs. Continuing in this way for some minutes, Keith reached back and lifted Debbie's legs, resting her calves on his shoulders. Guiding his cock into her pussy, Keith leant forward, pressing Debbie's knees back, nearly onto her shoulders. Debbie exhaled noisily as he fucked her in this position. The look of ecstasy on her face heightened Keith's excitement, especially as he could see his cock sliding into her well lubricated pussy, and he could feel his orgasm building.

🛍️ Featured Products

Premium apparel and accessories

Shop All →

'Turn round Debbie', Keith ordered as he withdrew. Debbie complied and positioning himself behind her on the bed, Keith guided his cock into her cunt. Gripping her by both hips, he began to fuck her, slowly at first before increasing the tempo. Debbie moaned each time Keith thrust deeply into her and Keith was surprised and delighted as she pushed back against each stroke. Feeling the pressure mounting, Keith drove hard for the last few strokes, burying his cock deep into her tight hole as he came, crying out as he did so.

Keith remained in position as his cock began to soften and withdrew, removing the condom and tying it, leaving it on the floor. The pair collapsed on the bed, Keith lying flat on his back, regaining his breath, with Debbie lying alongside him, an arm across his chest and a knee on his upper thighs. Keith kissed and her and as he toyed with her hair asked how she felt.

'Wonderful' replied Debbie. 'It was a bit sore to start with, but it went away. Can we do more?'

Keith laughed and said, 'Give me a minute to get my breath back!'

The couple lay together for a few minutes, resting after their exertions. Conscious of the time, Keith new that he had to continue to make the most of the situation. He reached over and began to fondle Debbie's breasts, noting with satisfaction that her nipples became instantly erect. As he did so, Debbie took his flaccid cock in her hand and slowly began to pump it. Keith could feel stirring but he needed more time to recover.

'I would love to spank you Debbie, if you're happy with that?'

'Mmmm, lovely' Debbie replied. 'Have I been a bad girl?' she continued, laughing.

Debbie positioned herself kneeling on the bed, her head buried in the pillows and her ass in the air. The sight of her pussy and ass from this position elated Keith, and he knew he would have no problem getting hard again. Running a finger down the crack of her ass to her cunt caused Debbie to shiver, and drawing back his hand Keith slapped her left buttock with reasonable force, causing Debbie to jump. He repeated this with her right buttock and then alternated for twenty slaps. As he continued, he could see that Debbie was enjoying the stinging feeling by the way she wriggled her hips and the soft whimpers she emitted every time he landed a slap.

Keith stopped and caressed her ass, which was red from the impact of the slaps. Kneeling behind her, he saw a bead of juice escaping from her cunt lips. He caught it with his finger and licked it off before sliding his finger along her slit to her ass and parting her ass cheeks, he noted with pleasure the little bud of her asshole.

Spreading her cheeks, he leant forward and blew on it, being rewarded by a spasm as it contracted. Spreading some saliva on his finger, he rubbed it round her asshole, before leaning in and tentatively licking it. Debbie moaned loudly and pushed back against him. Needing no invitation, Keith grabbed her cheeks and expertly rimmed her, stabbing his tongue at the puckered opening. As he did so, he asked Debbie to play with herself and was rewarded when he saw the girl's hand massage her cunt lips before concentrating on the hood which concealed her clitoris.

The combination of the rimming and the stimulation of her clitoris caused Debbie to come, crying out loudly. At that moment Keith was rewarded by the sight of her asshole spasming as the pleasure engulfed her.

Debbie collapse on the bed and as she turned round, Keith presented his by now erect cock in front of her face. Smiling, Debbie cupped Keith's balls and took his length in her mouth. Gently squeezing his balls as she bobbed her head up and down, Keith took her hand and placed it around the shaft, showing her how to squeeze and pump it. Catching on straight away, Debbie increased the tempo and Keith knew that a second orgasm wasn't far away. He gently forced his cock into her mouth as she sucked, causing Debbie to squeeze and pump quicker. As his orgasm loomed, he pushed her head whilst at the same time thrusting deep into her mouth. His cum hit the back of Debbie's throat causing her to gag initially however, she quickly recovered and continued to suck as Keith spasmed the last of his cum into her.

Sated, the pair lay together for a few minutes, before Keith, checking his phone, saw that it was time to get Debbie back.

' I could have stayed here all day' Debbie said as she pulled a clean pair of panties from her bag and stuffing her soaked ones back in it.

'Me too' Keith replied smiling, as he cleared up the bedroom, flushing the condom and smoothing the bed covers.

They were quiet on the journey back to drop Debbie off.

As they reached the car park, Keith said with a laugh;

'You've learnt some new things today.'

'More than I would have learnt in there' laughed Debbie, pointing to the school.

'See you next Friday for babysitting' Keith said as Debbie got out of the car, before adding;

'Remember to keep this to ourselves.'

Debbie winked and smiled.

The following Friday evening, Keith picked up Debbie as arranged.

'Have you been experimenting with your new skills yet' Keith asked as they drove.

'Not yet' said Debbie, 'but I have my eye on one or two guys.'

'By the way' she continued, my best friend Emma would like to meet you. I think you'll like her.'

Keith looked round in disbelief.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like