Maddy’s Mum Began My Education

"Is it on properly?"

Maddy couldn't see anything with my back half turned.

"Please make sure," she was really anxious.

"I'm actually more worried about your mum coming down," I had to say.

My cock was so hard and the condom was slippery in my fingers. As I turned, Maddy was spread backwards on the sofa in the half dark. Her panties were lying on the carpet beside us and her skirt just about covered her pussy.

"She won't, but just be quiet."

I turned awkwardly, my jeans and boxers around my ankles, and then I was getting on my knees between Maddy's legs. Leaning over her I fumbled underneath me trying to guide my cock towards her pussy.

I heard her little gasp as I pushed. Her pussy was so wet as I eased it inside her.

"Gently... please," she whispered.

It was our first time, and although I'd had sex before I wasn't very confident.

She was so tight, and the time Maddy had spent just rubbing my cock was my undoing. I'd barely thrust three or four times before I grunted.

"Oh god... I'm sorry!" I was distraught inside.

I lost all control and began jerking inside both the condom and her.

Maddy seemed to whimper and her whole body flopped. I quickly withdrew, and Maddy was asking, "Is it alright, it hasn't burst?"

Kneeling between her legs I looked down at my already softening cock. As I pulled it off I held the condom up in front of her.

"No, it's ok," adding ashamedly, "I'm really sorry, I couldn't hold on."

The condom was very full of my semen, stretching slightly because of the contents.

"Go and get rid of it down the loo, you know where it is, under the stairs, but be quiet."

I stood up, tugging my boxers and jeans up with one hand and creeping across the hallway and into the loo. Making sure it flushed away I got my trousers sorted and by the time I returned Maddy was dressed as well.

"I'm sorry," I said again, looking very depressed.

"Stop saying sorry, it's 'cos mum's upstairs, we'll get another chance. You go, I'll see you tomorrow at college."

We kissed and I left to walk home. I just hoped that Maddy wouldn't dump me because of it, or tell any of her friends at college that I was pretty useless.

Next day everything seemed fine, and although Maddy had changed her mind about seeing me that evening she asked me around on the Friday, and I knew everything was good when she said her mum was happy for me to stopover, if my parents were okay about it.

Both my parents knew Debbie Williams socially. When she split up from Maddy's dad they made a special effort to support her and that's how I got to become more friendly with Maddy.

Mum made sure I had all my change of clothes and wash stuff before I left on Friday evening.

"Don't forget to thank Debbie for having you," mum reminded me.

The fussing over, I arrived at Maddy's and she answered the door, kissing me briefly. Her mum appeared out of the kitchen looking like an older version of her.

Both were tall, blonde, and both had gorgeous breasts, Maddy's mum was mid forties, her breasts were a little bigger, as was her ass, although I knew it wasn't really appropriate to look too closely.

"Hi Matt, I see your mum's made you bring a bag." She half smiled and then directed Maddy to show me to my bedroom.

We'd barely got halfway up the stairs when she called after us, "And no hanky panky, come straight down, I've got drinks for you."

Maddy replied, "Stop it mum, don't embarrass me."

It didn't stop Maddy grabbing me and gripping my cock through my jeans once we were in the bedroom.

Five seconds later her mum called out, "Maddy!"

We both chuckled and went back downstairs.

"You'll be pleased to know I have to go out this evening, now can you two be trusted?"

Debbie had made some sangria for the three of us, and as we stood in the kitchen Maddy assured her mum that we could. We both knew we couldn't!

"Well I'm only going across the road to the Sharps.' They've got their twentieth anniversary coming up and they want me to do some of the catering, so we're gonna discuss that. It means I won't be late so just watch it!"

Our meal was a simple pasta dish with an ice cream dessert, and after watching some Netflix Debbie left saying goodbye, and reminding us, "Be good."

"You know what?" Maddy snuggled up to me.

"What?" I replied.

"Mum asked if you had any condoms?"

"Jeez, you mean she knows you and me might have sex?"

Maddy suddenly looked sad, and almost guilty.

"Im sorry, but I told her about the other night."

I groaned, and now her mum knew how useless I was.

"She heard us, and knew how quick it had been, and asked me."

"Oh Maddy," I must have looked really upset.

"Anyway, she seemed to understand, that's why she's gone out tonight, to let us be more relaxed. But she wants us to be safe."

My spirits lifted a bit and I turned to Maddy, even sliding my hand up under her top.

"Hey, slow down, we've got time now," she giggled.

Already I was kissing her neck, and reaching around her back searching for her bra fastening. She couldn't resist, I released her breasts and as I began to slide my finger tips over her nipples she began massaging my cock through my jeans.

"Let's go upstairs... to my room."

I needed no encouragement and we almost ran up the staircase. As soon as we were inside we were scrabbling to undress each other.

"Wait, let me close the curtains, and turn round, you've not seen me completely naked before."

I turned my back and heard the rustle of clothing being taken off.

"Ready!"

Maddy was in bed with the duvet pulled right up to her chin.

"That's not fair, you can see me undressing, you hide your eyes."

"No!... I want to see," she grinned, "and make sure you've got a condom ready."

I had a packet of condoms in my back pocket and put them on the bedside table.

"There... see."

I stripped off my t-shirt and kicked off my trainers. I was out of my socks and jeans in seconds, leaving me exposed in just my boxers. My cock was clearly stretching the fabric and Maddy was giggling again.

"Go on, I want to see how big you are."

When I revealed my erection her eyes widened.

"Come on, get into bed, I want to play with it."

I replied with a warning, "Just don't get me going like you did before."

Seeing me naked gave Maddy the courage to throw off the duvet and reveal herself. She looked incredible, and I was fascinated by the strip of carefully shaved hair between her thighs.

Leaning in we kissed briefly, enjoying the feeling of skin on skin. She felt so soft, her breasts wonderful against my chest. My cock was pushed against her thigh, and I was lost in the moment.

Both of us held each other in an embrace that seemed to go on and on.

"Oh Matt," was all Maddy said, as I pushed her down into the mattress, my leg slipping between her thighs, and bringing it right up against her pussy.

I rolled up above her, and she felt me pushing my other leg between her thighs.

"Matt, a condom!"

Just for a moment the head of my cock pressed against her wetness.

"No!... don't... please, put one on!"

I came to my senses and pushed myself off her, sitting on the side of the bed. Maddy raised herself on one elbow on her side and studied what I was doing. She saw the glistening of her own pussy juice on the head of my cock, as I tore open the sachet. Suddenly her head went down and I felt myself inside the warmth of her mouth.

"Oh fuck, Maddy, don't do that, you'll bring me off again."

For some reason, she didn't understand the logic of what I was saying, and went on sucking, seeming to want to take as much of me as she could. The sensation of her mouth sucking and the tickling sensation of her blonde hair against my thighs made me insist.

"Maddy! Jeez, stop! or you'll make me cum again."

Her bobbing head stopped and she lifted up, smiling.

"Mmmmm, can I do that, can I put it on you?"

I wasn't at all sure, even I fumbled to put a condom on.

She took the slippery ring of latex and I showed her the right way round. At first she tried doing it one handed, but soon realised it probably needed two sets of fingers. Sitting up she held my cock and began to unroll it over the head.

"Fuck, this is not a good idea," I mumbled.

She giggled and slowly rolled the condom down, her fingers slipping up and down my shaft.

I had to intervene.

"Here let me," I insisted until it was completely unrolled.

"Now you can fuck me!" she said gleefully.

She seemed so unaware of how far I'd gone. Maybe naïveté or just not knowing how men worked.

Willingly I slid between her thighs, her legs opening wide and her ankles clasping behind my buttocks.

"Just be still... please I said."

I think she tried, but whether she knew that her pussy muscles had a mind of their own, I began to cum.

"Oh god, oh god," I muttered into her neck, "Fuck, I've done it again."

I felt myself jerking deep into her, I'd tried and failed yet again, and I was so angry with myself.

As I finished cumming, Maddy realised we'd rushed it all again.

"Please, don't be upset, I'm sorry too, it was partly my fault, please Matt!"

With the sexual release I panicked and wondered if the condom had held. I rolled off and we both looked down. The condom was full and intact like before.

"Let me take it off," Maddy said unexpectedly," I put it on, I'll take it off."

"Be careful," I said as she tried to roll it off, "it's easier just to pull it off."

My cock was diminishing and as she pulled, it spilt some of my semen onto the bedsheets. I muttered and she giggled, "Yuk!"

"I'll go and flush it," I said and took it from her, departing to the bathroom. When I returned she was lying naked and holding her arms out to me.

"Come here, we'll get there eventually."

I sat on the side of the bed looking downcast.

"You haven't cum, I'm pretty useless aren't I?"

"No you're not, and it doesn't matter that I haven't cum."

"Hmmm, you better buy a toy, a vibrator or something."

"I've got one!" she giggled.

"You haven't," I half disbelieved her, "I'd better get dressed and leave you to use that, it'll be better than me."

"Stop it!," she stuck her nails into my thigh making me yelp.

"Ouch!"

She smiled, "Stop feeling sorry for yourself."

I watched as Maddy leaned over and reached under the bed.

"Surprise, surprise!"

In her hand was a pink, cylinder, about six inches long.

"Promise to watch."

I was gobsmacked and fascinated at the same time. I watched as she pushed the vibrator between her thighs. The buzzing began and I saw it being moved backwards and forwards between her pussy lips, and then it sliding inside her about three inches deep.

Her eyes closed and there was the softest of groans.

There was another longer groan when she held the vibrator against her clit.

"Ohhhhh, gosh," she gasped, "Matt, kiss me."

I leaned forward and gently kissed her, her mouth already open. In moments I felt her body lifting off the bed beneath me, then starting to shake.

Pulling away from my kiss she was gasping, "Ohhhh, fuck, fuck, fuck," until the buzzing stopped and l lifted up to see her lying there, her eyes still closed, and moaning a soft, "Mmmmmm."

"I was so close with you, it felt so good to have you here."

I was still feeling inadequate, but excited by what I'd seen.

At that moment the landline rang downstairs. Three rings and it stopped.

"That means mum will be home soon. We'd better get dressed."

Maddy's bedsheet had a damp patch that she hoped might disappear, we tidied up the pillows and duvet and got dressed, then went downstairs.

There was a text on Maddy's mobile saying, 'Home at 10.'

It was nine forty five, so we turned the tv back on and made a coffee.

"Been good?" was the greeting from Debbie as she arrived home.

"Of course," replied Maddy, and I just remained silent.

"Had you remembered your dance lesson tomorrow, I'd forgotten until Linda Sharp reminded me. Mr Sharp will be outside at nine, with Caitlin."

"Do I have to go, Matt's here."

"You'll be back by soon after eleven, you can stop on for lunch can't you Matt?"

I wasn't expected home until later anyway, so I agreed to stop.

"Yes I can stop, if you want?" I looked across at Maddy.

"Of course I do, you can sleep in after I've gone."

Both Maddy and I were waiting for Debbie to go to bed leaving us alone again, but by the time the news on tv had finished I was ready for bed anyway, and excused myself to go upstairs.

"The towels are on your bed Matt, I won't wake you in the morning."

I thanked her and left the two of them chatting and made my way to my room. I must have fallen straight to sleep and was only woken up by the birds singing outside.

I looked at my phone and there was a text from Maddy.

"Don't worry xx."

It was timed the previous evening so I texted back, 'Thank you xx.'

It was then I heard the movements from downstairs, it was almost nine and later than I thought. I heard a car start up outside, the front door close, and then the car door slam before driving off.

I needed to go to the loo. Thinking Debbie was downstairs in the kitchen I wandered out to the bathroom. Returning from the bathroom, I heard a floorboard creak and Debbie appeared from out of Maddy's room.

I felt completely naked, even though I had my pyjama shorts on.

"Oh... I'm sorry, Mrs Williams, I mean Debbie, I thought you were downstairs."

Debbie grinned. She was still wearing her bathrobe, and was amused by my embarrassment.

"No need to be embarrassed Matt, I was just tidying Maddy's room. I won't look."

But she was looking.

I tried to half turn, and instinctively put one hand down to shield my crotch from view.

"Go and get dressed," she added, "just let me get something out of the cupboard in your room."

She followed me in and went to the cupboard on the far side of the bed. Casually she asked, "Did you sleep well? Was the bed okay?"

"Yes, fine, I slept like a log."

She reached up to the top shelf and I was trying not to look at her calves and lower thighs as her bathrobe pulled up.

"I'm afraid Maddy and I stayed up chatting."

I felt myself going red, because I knew that if Maddy had shared our difficulties the first time, she'd probably done it again.

She closed the cupboard door and turned back, seeing my flushed face.

"Why don't you sit down Matt, can we talk?"

I had to say yes, to say no would have made the situation doubly awkward. I sat on the side of the bed knowing what might be coming.

"Shall I get dressed first?" I said.

"No, it's okay, this won't take long."

My face was still burning, suspecting an awkward conversation.

"Maddy told me something."

She was watching me closely and sat down beside me.

"You probably know what I'm going to say."

I was almost choking with embarrassment now.

"I think so," I croaked.

"I want to assure you your problem's nothing to worry about. It's something that happens when you're young, and when you're not very experienced."

I whispered, "I know," which seemed a bit pathetic.

She fidgeted and seemed to move closer, and I could smell her perfume.

"Maddy's not too concerned, but she's worried that she's doing the wrong thing too."

"She's not, it's just me," I replied.

Debbie leaned forward to place a hand on my arm to reassure me. It was difficult to hold eye contact, I was so embarrassed and by now very nervous. Because she was leaning towards me her bathrobe tie had loosened and the neckline gaped open, massively exposing her cleavage.

She plainly knew that I was looking.

"Sorry, I should have got dressed before we had this talk, shouldn't I?"

She was waiting for an an answer.

"No, you didn't have to," my voice was strained, wondering if I'd said the right thing.

That seemed to encourage her.

"I'm pleased you said that, you know why?"

"No?" my heart was beating out of my chest as Debbie seemed to show even more of her breasts as she edged a closer.

"I think we need to do a bit of coaching."

She could see the puzzled expression on my face, but she was also aware that her flirting had begun to see a reaction in my shorts.

I watched as her hands moved to the bathrobe tie. She tugged it, and pulled the two ends apart. The robe fell open and I saw most of her body exposed, along with the same carefully clipped strip of hair as Maddy had between her thighs.

"Now lie back."

I hesitated and then allowed myself to be gently pushed backwards across the bed, not believing what was happening, and watching her slip out of her robe.

"Just let me show you, keep telling me how you're feeling, but close your eyes."

Debbie's fingers touched my chest and her nails travelled over first one nipple then the other. I was holding my breath, her nails were dragging towards the waistband of my pyjama shorts.

Even expecting it, I wasn't ready for when she tugged my shorts down. She pulled them right down leaving me naked. The soft wet feeling of her mouth made me groan, and the enveloping glove of her throat pushing down around the head of my cock was testing me straightaway.

"Oh fuck, slowly... please."

Lifting her head she spat a long drool of saliva onto my cock, spreading it up and down the shaft with one hand.

"Should we be doing this?" I was lost.

"Yes!... now tell me if you're close." She said it quietly as she shifted her body to kneel between my legs.

She was leaning over gripping my cock with both hands. All I could see was her blonde hair hanging forward as she concentrated on wanking me.

"God, I'm not far off... wait." I groaned.

I was tensing the whole of my body when I screamed out, "FUCK...!"

I wasn't expecting what Debbie did.

The tip of my cock was being squeezed hard between Debbie's thumb and finger. She held it for quite a few seconds before letting it go.

"Has that slowed you down?" she asked calmly.

"Fucking hell!" I whimpered.

"Well has it?"

The threat had in fact gone away, and I raised my head and opened my eyes.

"I think so," I whimpered.

"Tell me straightaway again then." and I saw her head lower and the warmth of her mouth returned.

"Ohhhh fuck, Debbie, slow down," and she did.

She just stopped moving, holding me there in her mouth, in her wet grip.

I tried to relax, but the feeling of cumming crept back. A minute later I was panicking again.

"Debbie, I think I'm gonna cum."

She lifted up once again and gripped my cock hard with her fingers and thumb. It was harder than last time... and she held on.

"Jesus... god Debbie... ahhhhhhh!"

Eventually she let go.

"You've done great, you're hanging in there, now I won't do that again, next time you don't hold back, just see how long you can last."

It all felt so crazy, as Debbie took me into her mouth once more, and again she hardly moved, she just held me firmly, surrounding my cock with the softness of her tongue and cheeks.

I called on all my resolve, I thought of bizarre things, and managed to hang on for maybe a couple of minutes, and then it became too much.

"I'm cumming Debbie... please, I'm cumming!"

In an explosion of so much pleasure my cock jerked, and kept jerking. I couldn't believe I was still in her mouth. She worked it up and down and I could feel her swallowing every drop.

"OHHHHH! FUCK!...." my cry of pleasure went on as she continued to suck until I jerked no more.

"Jesus Debbie, this is crazy." I said.

"Maybe, but you need to learn, you need to practise."

It was the weirdest thing when she stood up beside the bed, naked. She picked up her bathrobe and put it on.

"You get dressed and wait downstairs, I'm gonna take a shower. I don't think I need to tell you about not saying anything to Maddy, to anyone... promise me for god's sake!"