A First Time for Us Both

Names changed, but this is the true story of my girlfriend and i losing our virginity.

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My father dropped me off at the staff accommodation early as he had to get to work. It was a converted barn in the village, with room for 6 of us to live. This year there were 4 lads sharing a room, and across the hall a room with two girls in. It made a change from last season when it had been only lads staying there. I quickly dropped my bag on the last spare bed, grabbed a few things for the day and headed downstairs.

Quick introductions were made to the new faces, and I was welcomed back by a couple of guys who I had worked with last year. They had been here a few weeks already, having more summer holiday as university students than I had at my last couple of years of school. Also new was Adele, a petite dark-haired girl dressed in a blue rash vest and shorts, apparently the new windsurf instructor and from southern England.

Within a few minutes we all started to head out the door into the bright sunshine of July in the UK. The sailing centre we all worked at was a few miles away down the side of a Lake. As we all loaded our bags I suddenly realised that there were not enough seats in the small car.

"No worries" said Gareth "the new staff member is coming, she is called Jo, and you need to show her the way to work!." With that, he leapt into his drivers seat and floored it out the gate. Almost immediately I heard a squeal of tyres, and so I rushed out the gate and peered past the house myself. Gareth's car was stationary and facing it in the narrow lane was a very cool looking bright orange mini with an attractive blonde girl of about my age behind the wheel. The two cars were reversed enough so that Gareth could exit, and almost immediately the mini pulled up alongside me.

"Is this the sailing centre accommodation?" she asked through the open passenger window I had leaned down to look into.

"You must be Jo?" I replied, and geekily offered a handshake through the window. "Come on, I will show you your room."

I helped carry her bags in from the back seat of the car, introduced her to the landlady and family, and then took her for the quick tour of the bedrooms, bathroom and small downstairs lounge. All the time I could not help but notice her lovely smile and gentle character. She seemed almost shy and barely spoke, but was clearly being introduced to a lot of new people and a new place in a short amount of time.

"We need to go" I told her "Apparently you are using your car for the season?" This was something arranged by the boss who paid car owners mileage.

"Yeah, apparently so" she smiled "But I don't know how to get from here to the centre -- I assume you do?"

"I do, come on, lets go" I replied.

Climbing into the mini was an eye opener. It had a full roll cage and bucket seats, and a custom dash. As I hunted for the harness I admired her long tanned legs and short running shorts, her vest top which clung to her small but seemingly very pert breasts.

"Wow. This is, well, different" I commented.

She smiled, putting on her sunglasses and starting the car while also explaining her father ran a business renovating mini's, and many of the family took part in some form of motorsports as well as sailing. She as a slim 5'6", clearly athletic as a runner and sailor, and she could throw that mini around corners with a confidence and skill I could only marvel at. It transpires she was nearly a year older than me but in the same year group at school, heading to university like me a the end of the summer, and both raced sailing dinghies when not instructing in them. That 8-mile journey to work up the side of the lake on a sunny day, in a cool car with frankly a beautiful young lady had me utterly smitten.

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A month later Jo and I had been going out for a couple of weeks. I had asked her out properly at my 18th birthday party, and since then we had both taken many evening walks, but also managed a couple of meals out in local pubs. Being away from the others was a challenge -- we all shared a house, worked together and tended to socialise together. That said, we found opportunity where we could but had not yet managed a full day off together. We had also kissed and held hands, but very little else as the house always had someone there, we had shared bedrooms, and the local pub was rather inappropriate for such things. Jo was a passionate kisser, and quite constant in small touches and handholding where we could. We did discuss finding quieter places and the need for more kissing and perhaps more.

Finally, we had a day off together and so headed off across the mountains in her mini to climb a hill above another lake. Later that day we found ourselves sat against a boulder enjoying a picnic with a view across the mountains without anyone else around. Our kissing became petting, Jo happy for me to slide my hand under her top and feel her lovely b-cup breasts. They had lovely small nipples, rock hard under my fingers, and drew some moans from Jo. She in turn was running her hands over my body, and confidently straddled me to continue our kissing, slightly dry humping me as well. Sadly, this was interrupted by some more walkers coming up the hill.

As I drove us home Jo had her hand on my thigh, lightly rubbing at times and so high up I thought she was going to stroke my cock.

"Are we going with the others to the pub tonight? I asked. It was Saturday night, and all the centre team tended to head out for a few pints.

"I fancy a night in" she said with a smile.

"Oh reallly.....?" I laughingly replied.

"Yeah. I think you and me need to have a date" she replied

"Well you and me need to kiss some more, I know that" was my reply, to which she squeezed my thigh.

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Back at the accommodation we had a meal with all the staff and the host family, before heading into the staff lounge. We put on a video and cuddled up on the corner sofa, my arm around her shoulders and Jo leaning against me.

Pretty soon everyone headed out to the pub, with more than a few jibes about what Jo and I would be getting up to as they left the glass door from the lounge into the garden.

We both sat for a while watching the film, slightly awkward as only inexperienced teenagers are. Finally, I felt her hand slide back onto my thigh again, and I took that as a cue to also begin to softly slide my hand around her shoulders, hand slowly roaming over her belly and edge of her breasts.

After a few minutes of this, I pulled up her t-shirt slightly and so my hand was touching her bare stomach. Jo turned, leaned in, and we kissed. Our tongues entwining, our lips keen to explore each other. Our hands began to move again, Jo pulling my face to hers, my hand roaming around her back. We continued for a while, slightly changing position so that once again I could feel her breast. Under her plain white cotton bra I could feel her bullet like nipple again, but struggled to move the fabric aside.

"We can be seen here" said Jo, breaking off the kiss and motioning to the door. She was right -- anyone coming back from the pub or visiting the house could see straight into the door. "Lets go upstairs"

And with that she led me by hand upstairs, into her room.

Her single bed was against the wall, Adele's bed further down the narrow room. I closed the door and we both sat against the wall on her bed and resumed our kissing. Soon I was back on her breast, trying to make skin contact. Jo disconnected, reached behind herself and unclasped her bra, but did not remove it or take off her t-shirt. I reach back in to kiss her and slid my hand up under her bra.

Jo gasped and grabbed my wrist, I thought at first to stop me, but in fact she was encouraging my contact. Her breasts felt warm and firm, her aureole crinkled and crowned with those hard nipples I had already felt. As we kissed, I felt Jo pull me towards her, back towards the pillows to lie down.

Still dressed, I could feel my raging cock straining against my underwear and jeans. I was sure Jo must have felt it too, as I rolled slightly over her. We kissed more and I slid my hand down from her breast to her waist, sliding over her belly, back lower across the waistband of her jogger bottoms, and finally over her mons. I tried to be all nonchalant, and carried on sliding my hand from breast, side, and across her waist, eventually sliding fingers under the waistband of her joggers and feeling the top of her underwear. She spread her legs slightly, an invite to explore further, and my fingers slid over her knickers, feeling her bush and a heat.

"Stop, we need to talk" she gasped. "I haven't been all the way before"

I stared at her "It is OK, there is no pressure" I replied, thinking that this was maybe as far as things were going to go. I kissed her again. "Whatever you are comfortable with" I assured.

"But I think I want to" she replied, looking me in the eye. "But I am a virgin. But I want to lose it"

"I am too" I replied.

"What? I thought you must have....." she mused.

"Nope. Never went that far"

She kissed me back. "Well what do you think? Should we?"

Now asking 18-year-old me if I wanted sex was only every going to get one reply.

"yeah. That would be nice." I was trying to play it calmly. "I bought some condoms, I will go get" and I made a move to climb off the bed.

"No need -- I have some here." She rolled away slightly and opened her make up bag on the bedside table and pulled out a pack with a smile.

We kissed, deeply, and my hand slid up her side again to her breasts, this time with a new found confidence and permission. Jo melted under me, relaxing like she had not so far.

Interrupting, she sat up and removed her top, but also to my surprise when she lay back down, slid off her joggers and knickers. I gazed at her tight athletic body, her pert breasts standing proud with light coloured puffy nipples, a slim waist and boyish hips, but with a lovely curve across her mons to a dusky light coloured bush. She had the most amazing difference between her tanned areas and bright white where she covered up from the sun at work each day. She was the first girlfriend I had seen naked, and the response from my cock was immense, almost painful.

"I am cold" she said, and wriggled away, trying to slide into the duvet we were lying on. I got up, allowing her in, but then climbed over her and stood up. I removed my own t-shirt, and then bashfully for the first time, undid my belt and slid down my jeans and boxers in one go. I had to unhook my cock from my underwear as it stood proud. Jo was eyes wide and smiling, looking very intently at my cock and back to my face, admitting afterwards it was the first one she had seen.

Inelegantly I then reached down and pulled off my socks, before sliding back onto the bed and under the duvet. Jo rolled towards me, her hands pulling me close, and her lips once again keen to find mine. Our bodies generated incredible heat, the new sensations of being completely unencumbered by clothes was one I will never forget.

Our hands were roaming, and hers reached my cock before mine found her pussy. Her fingers closed gently around me and I groaned. Her touch was nervous, light, and unskilled, but it was glorious as she felt me and tried to move her hand slightly.

"It is so big" she whispered "are you sure it will fit?". She was genuinely nervous, and I have since found, had a right to be as I am thicker than most. Back then I was also slim, bordering on skinny, and so my cock really stood out in size compared to the rest of me.

I rolled her over on her back, assuring her we would take it easy and I would stop if she wanted. My hand slid over her arm, reaching for her pussy. She was only the second girl I had fingered, and it took a clumsy few moments of sliding through her bush and finding a wet trail, heat, and a new shape of pussy to explore. But my fingers soon found her slit, a wee nub of a clit and her soaking wet hole. I slid back and forth gently, not yet skilled in the art of frigging a woman.

My finger was now sliding in and out of her small hole, soaked with juices, and eliciting a moan from Jo each time I slid over her clit. Her breast pressed against my chest, legs open slightly, and her hand now holding my cock without moving.

I rolled onto her slightly, my cock pressing into her stomach, and I kissed her intensely. She pushed me back slightly. "Best put that on" she said head motioning to the box of condoms. I sat up out the edge of the bed and began the process of putting on my first condom. To say it was somewhat awkward is an understatement, and it took a couple of goes to get it the right way on and rolled down. Jo was watching as I did so, but she made no physical contact as I struggled.

I turned back into bed and Jo opened the duvet, pulled me over onto her, sliding her legs wider and pulling on my hip to position me above her. I paused, my hips now between her legs, my weight resting on my arms, feeling her breasts squashed against my chest. My eyes looked intently at her, her face now fearful, almost tearful. "Are you sure?" My head told me to stop looking at her face, despite the opposite message from my loins. She nodded.

I slid upwards a bit, my cockhead sliding up her thigh and into the fold of her leg. I repositioned, moving up her body and lifting my weight from her. I felt the heat of her slick hole as my cock found her entrance. I tried to move slowly and pushed forward, but my cock just slid upwards. I reached down and pressed my cockhead back down and felt the warmth spreading over my tip. I pushed again and Jo winced, this time I was in the right place, but seemed unable to get any further. I rocked back and forth slightly, but each time was met with no way forward. I pressed harder, her tunnel now accommodating a few centimeters of my rock-hard erection.

"Ow" she squealed and recoiled.

I stopped "are you OK"

"Of course I am, it just hurts first time doesn't it?" she almost snapped at me, and with that she pulled on my hips some more to encourage me deeper. I was less forceful in my pressing in, by now I was sliding about 1/4 of my cock in and out slowly but feeling no way through and watching her face as she felt some more pain. After a minute or two, I tried again to push deeper, but found I slid out of her slit again, missing my target.

"Why don't we try you on top?" I meekly suggested "You have the control then"

We disconnected and she rolled on top, but to my surprise sat up some. She had one leg crouched, the other folded under her. She took my cock and pointed it into her depths, easily finding her entrance, which I studiously looked at in the light. My condom clad cock started to slide in again, but was once again met my resistance.

I looked up -- Jo had her eyes closed and was clearly in some pain. But her weight bore down, and suddenly I slid deep into her. She stopped, wincing and gasping slightly. Her eyes opened and she looked at me, looking very emotional. Our eyes connected and I sat up to kiss her, she responded by holding my face and kissing me deeply back.

She lifted slightly, and then slid back down again. She repeated this, each time getting me another fraction deeper, until our bodies prevented any deeper penetration. My loins were on fire -- her pussy was everything a teenage boy dreams of. So tight, so hot, so slick. Both grasping and yet offering little resistance now I was in.

She lifted, this time almost completely off me, and started to move slightly up and down, her pussy entrance over my cock head, but not very deep. She folded her second leg under her and tried to build a rhythm up and down.

I now reached for those magnificent youthful breasts as they jutted out, impressive despite their modest size. My hips began to try and match her pace, but our inexperience showed as we struggled to make it work for both of us. I lowered a hand to find her clit, and began to circle it as we made love.

I felt it rising, as the sensations seemed to increase in intensity. I slowed my hip movement and whispered "Hang on, I am nearly cumming". Jo opened her eyes and carried on, slowly moving up and down. "No really, you need to stop a moment" I pleaded, but with that she slid back down deeper on me, and that was enough. I exploded inside the sheath, ropes of my thick young sperm filling the space, my cock swelling even more. My orgasm was huge and I groaned openly, pressing into her and squeezing her tit involuntarily.

Jo slid up and stopped. She looked at me intently. "That was nice" she said, smiling. My reply was a kiss and agreement.

I reached down to touch her clit again, but she moved my hand away.

"I am so sore" she said, and slid off me, my cock slapping against my own belly. I looked down at some blood on both of us, and a condom full of my seed.

She reached for a tissue box on the nightstand, and as I took it off her, she hopped off me and quickly disappeared through the bedroom door and into the bathroom.

A few minutes later we were cuddled up in bed, me apologising for cumming too soon and how much pain it had caused, her assuring me it was fine and she had not expected fireworks first time. We chatted a few minutes longer, and I offered round two as my youthful cock had not reduced its rigidity at all since we had finished. Jo was adamant that once was enough for the night being sore, but perhaps we should try again tomorrow.

We kissed deeply again, and all but fell asleep entwined together. We startled at the sound of the front door being opened and drunken voices as the pub-goers returned. We both froze, listening to the voices and the steps on the stairs, followed by the bathroom door. I jumped out of bed and started dressing, only to have the door in front of me burst open to reveal a smiling and drunk Adele.

"Oooh" she squealed "I know what's going on here" she roared, eyeing my nakedness up from head to toe.

"Fuck off" I replied and pushed her out the door, closing it behind.

Jo and I laughed as we dressed, the peaceful evening over.

We only ever had sex three times that summer. Between 6 people sharing two bedrooms, 6 days a week work, and the end of the summer a fortnight later, we barely found opportunity to kiss let alone fuck. The next two times were better, and I was proud that I learned enough about her to deliver her first orgasm, a short, physically jolting, and flushed affair as she grasped my hand encouraging me on.

We said goodbye on a lovely sunny summers evening as she tore off in that cool car, away to the south of England while I headed to a Scottish university. With 350miles between us, busy courses, and a lack of train fare money, we never met again.

I regularly think of her, my virginity losing beauty, and wonder if we will still feel a frisson of excitement should we meet again.