Written by Ben

19 Apr 2017

It's probably fair to say I was a bit of a geek when I was a teenager. I studied hard and got good grades, and wasn't really into sports. I did have plenty of friends at school, male and female, but I was the classic boy who got 'friend zoned' by the girls. I wasn't bad looking in a geeky sort of way, slim with wavy brown hair and glasses but the girls seemed to go for the more 'laddy' types on the football and rugby teams. Because I was quiet and a bit shy, a few people (including my mum) had wondered if I was gay, which annoyed me because I definitely wasn't! I fancied several girls in my year but never had the confidence to do anything about it. Instead I took care of my pent-up sexual frustration by masturbating to porn videos in bed at night and thinking about the girls at school I liked. A few of my friends claimed to have had sex (although I'm not sure I believed all of their stories) and I felt annoyed that I was still a total virgin at 18.

I had been having piano lessons since I was 11 and had become a pretty decent player. My teacher, Helen, had encouraged me to stick at it and by the time I was 18 and in my final year of sixth form I was about to take my Grade 8 exam, hoping to get into a conservatoire to study music. Helen was in her early 40s and had a couple of younger children but had divorced her husband a few years earlier. As my hormones had kicked in I'd begun to think she was quite attractive, she looked younger than her age and I guess you could say I had a bit of a crush on her. I'd even managed to find a video featuring a woman who looked a bit like her and I have to admit it became one of my favourite to wank off to. Quite often she'd sit on the piano stool next to me to show me a tricky bit and I always enjoyed feeling her body pressed up against mine. I loved the perfume she always wore and sometimes in the warmer weather when she was wearing a more low cut top I couldn't resist a cheeky peek when she was concentrating on playing. This always gave me a bit of a thrill and I had to be careful not to get too excited and embarrass myself, but it was basically just harmless fun. Or so I thought...

We were coming to the end of my weekly lesson on a warm summer's evening and I was getting ready to pack my books up and head home. Helen then surprised me by saying she'd had a long day and needed a glass of wine but hated drinking alone - I was 18 now so would I like to join her? I was a little taken aback but thought I might as well, my mum was working late that night so all I had to look forward to at home was a microwave meal. "Erm thanks, that sounds good" I replied. "Go and grab a seat on the sofa then and I'll fetch a bottle" she said. I went through to the sitting room and sat down. Helen came in with a bottle of pinot and sat next to me on the sofa, pouring us each a glass.

"I've been so impressed with your effort recently Ben", she said, "you're going to ace your exam!"

"Thanks Helen, I really appreciate all the help you've given me" I replied.

"You're welcome, you're one of my longest standing pupils now and I'm going to be sorry to lose you when you head off to college next year".

"Yeah, it's been a while hasn't it!"

"I was so pleased that you stuck with it, a lot of pupils lose interest when they get into sixth form, too many other distractions like girls and parties! Do you have a girlfriend yet Ben?"

"Umm no I don't" I replied knowing I was blushing a little.

"Oh I'm surprised, thought they'd be queuing up for a handsome lad like you!"

That definitely made me blush, although I just took it as a bit of teasing and didn't really think any of it.

"Not exactly, maybe it'll be different when I get to uni".

"Oh I'm sure it will, you'll have a great time" she said, with a wink which threw me slightly.

She changed the subject back to music and we chatted for a while longer. I didn't even notice her topping up our glasses, I wasn't too used to drinking wine and it was going to my head a little. I tried not to show it as I was enjoying being treated as an adult and didn't want to look immature. The conversation turned to my upcoming exam and, loosened up a little by the wine, I admitted to Helen I was actually feeling a bit nervous about it as one of the pieces was proving really hard to master.

"Oh don't worry, we'll do plenty of work on it so it's perfect by the time of the exam" she said. "You've got nothing to worry about Ben", and as she said this to my surprise she put her hand on my thigh and gave it a little squeeze. I tensed slightly at the unexpected touch and she quickly withdrew it.

"I'm sorry Ben, I don't know why I did that" she said looking embarrassed.

"Erm it's ok Helen, don't worry about it" I replied.

"You just looked pretty worried so I wanted to reassure you but I shouldn't have done that" she said looking away from me.

"Honestly, it's fine" I said knowing I was blushing massively. "You've always been great at encouraging me".

"You're a great pupil Ben, you work so hard and I'm going to make sure you get what you deserve" she said looking a little more relaxed.

"I couldn't ask for a more supportive teacher" I replied giving her a smile to show her I wasn't annoyed or upset.

There was a little silence then as we both took a sip of our wine.

"I still can't believe you haven't got a girlfriend" she said, "handsome clever lad like you".

"Ah well the girls seem to go for the sporty boys, and I guess I'm more of a geek".

"You just need to find one who appreciates a talented musician" she smiled.

"Yeah I live in hope" I grinned back.

"If I was 20 years younger I'd be all over a lad like you" she said and her hand once more went onto my leg.

Feeling Helen's hand on my leg a second time had an effect on me and I felt myself starting to get a stiffy. It was probably the wine making me less inhibited but this time I didn't flinch. I turned to face her and she was staring back at me. I don't know where the confidence came from but I moved my face towards hers and our lips touched. We both drew back looking a little shocked but then she began kissing me again and this time we parted our lips allowing our tongues to touch. I didn't really know what I was doing so I let her lead the way, it felt like it went on for ages even though it was probably only a few seconds.

"Ben, you're an adult now but I need to know you're totally comfortable with this. There is absolutely no pressure and if you want to go home now we'll never mention this again". She looked nervous as if she'd crossed a line.

I didn't know what to say so I just leaned in and kissed her again, feeling my dick reach full hardness in my jeans. We kissed passionately, our hands starting to explore each other's bodies. She guided my left hand towards her chest and I touched a woman's boobs for the first time. Her hand traced up my thigh before grazing over my crotch and I knew she could feel my arousal. No words were spoken, but we knew we both wanted more. She broke off our kiss and asked me again "are you sure?" I nodded, and she took my hand and led me out of the room and up the stairs.

We got into her bedroom with a massive double bed. I felt a little nervous being totally inexperienced but because I knew Helen so well I trusted her. I was flattered that she'd be in any way interested in me and decided I would just go with it and see what happened. We sat on the edge of the bed and kissed some more, hands wandering over each other's bodies, our breathing getting heavier. I suddenly realised I didn't really have a clue what to do next, this was totally new territory for me. Luckily Helen took the lead.

"Come and join me up here" she said patting the pillow.

I quickly took my shoes and socks off and scooted up the bed. We resumed our kissing and I was still rock hard in my tight skinny jeans. When we broke off she took my glasses off before tugging my t-shirt over my head revealing my skinny but slightly hairy chest with a thicker treasure trail leading down into my jeans. "Oh Ben," she giggled, "I didn't expect you to be so hairy! Although I know you've got pretty hairy legs from seeing you in shorts" I blushed and she then took my hand and helped her take her top off, revealing her lovely big boobs in a black lacy bra. "Oh wow" I whispered. I reached out to feel them and we kissed some more before I felt her hand move onto my bulge. It felt so good I was worried I was going to lose it there and then but I managed to control myself. She began fumbling with my buttons and they came open. "Do you want to take them off Ben?" she asked, I nodded and slowly pulled them down. Now in just my tight boxers and with my erection clearly visible I suddenly felt very vulnerable and exposed but also incredibly turned on. When I looked over Helen had also taken her jeans off, lying on the bed in her matching bra and panties. These sights were all new to me and I couldn't believe how sexy she looked. She got close to me and stroked my thighs, teasing me before brushing her hand against my penis.

"Is this your first time, Ben?" she whispered.

I nodded nervously. "Don't worry, we'll take it nice and slow and we can stop any time you like".

Not likely, I thought to myself as again I felt Helen's hand against my boner. I shuddered as I felt her hand slip under my waistband and for the first time I felt someone else's hand wrap around my aching dick. I couldn't help moaning a little, it just felt so good, even better than I'd imagined.

"Does that feel good Ben?" she asked.

"Mmhmm" was all I could manage in response.

"Let's have a look at him" she smiled easing down my pants until my cock popped out.

I was a little shy at what she'd think of it, I won't lie and pretend I'm massive, I've got a pretty average 6 incher but she seemed to like what she saw. "Mmm Ben, that's just beautiful" she said running her fingers through my pubic hair and wrapping them around my shaft. She gave it a couple of tugs before taking her bra off, letting her lovely boobs go free. I reached out to stroke them and without thinking leant forward and kissed one of them. She gave me an encouraging smile and so I latched onto her hard nipple and started to suck before switching to the other one. She was stroking my shoulders as I did it and I heard her moan softly. She gently pushed me down onto my back and once more took hold of my cock.

Nothing prepared me for what came next as she leant her head down and gently flicked her tongue across the tip. She did this a couple of times before slowly taking it in her warm wet mouth. I had always wondered what a blowjob would feel like and it was just amazing, a couple more sucks and I suddenly knew I couldn't hold back any longer, I barely had time to warn her before I started shooting my cum. She was obviously experienced and managed to swallow pretty much all of it.

"Wow Ben, you certainly seemed to enjoy that...I saw you wiggling your toes so I guessed you were close! I'm sure you're not done yet, though, are you?"

I shook my head giving her an embarrassed smile. "Would you like to try it on me now?" she asked.

I didn't need any more encouragement and scooted down the bed. I could already smell the scent coming from between her legs. She slipped off her panties and I got my first look at her beautiful vagina. She was not shaved like a lot of women in the videos I watched, but her pubes were neatly trimmed and I found it incredibly sexy. Although I'd seen those videos and read loads about how to eat pussy, I was still a little apprehensive. I leaned down and tentatively licked the area around her hole. The taste was so new and so good. She shuddered and I got a little bolder, running my tongue around in little circles hoping I was doing it right. From the little moans I could hear she seemed to be enjoying it. When my tongue made contact with her clit she squealed and told me to take a break.

"You're a fast learner Ben, just like on the piano" she giggled and I couldn't help laughing too. She kissed me again and I could feel my cock getting hard again.

She noticed and said "I see someone's waking up again...there is something else we could do, that's if you want to"

"I want it so much" I replied.

"As long as you're sure", she said, "I'm on the pill so it's totally safe".

As it was my first time, she got me to lie on my back, my now rock hard dick pointing skywards. She moved over me and lowered herself slowly down onto it, as I felt her hot hole around my aching shaft I couldn't believe I was losing my virginity with this sexy lady I'd known for years. When it was all the way in she stopped to check I was ok before slowly rising up and back down. I knew I wasn't going to last long but didn't want to embarrass myself by cumming too quickly. I reached up to hold her boobs as she continued to move on me. Now I was used to the feeling I relaxed a little and enjoyed the sensations running through my body. She started to bounce a little faster now and was rubbing her finger against her clit. We were both moaning, she got louder then suddenly squealed as I felt her pussy start to pulse around my cock. I couldn't take any more and began shooting my load deep inside her.

As we came down from our intense orgasms I think the reality of what had happened began to dawn on us. She asked me if I was ok and I reassured her I had wanted it and it was beyond incredible. I said I had better get home and we kissed before getting dressed and heading downstairs. When I got home I jumped in the shower and could barely believe what we'd done, masturbating to yet another orgasm thinking about Helen's sexy body.

The next lesson was a little awkward at first, neither of us seemed too sure whether the other would regret it. In the end, Helen brought it up and we agreed things had maybe got a little out of hand not helped by the wine but at the time we both wanted to. Nothing happened between us again and a few months later I headed off to university. Helen messaged me a few times to see how my studies were going but moved away during my first year so I never saw her in person again. That experience did boost my confidence with girls hugely and I found a girlfriend on my course. We have amazing sex but I'll never forget that first crazy experience.