Losing My Virginity…..at 18

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By way of introduction, my name’s Tom and at eighteen I had been late developing at puberty.

I attended an all boys grammar school in south-east London.

In the first three or four years, I had been self-conscious about getting changed for PE lessons because of my lack of pubic hair and small genitals, but by the age of eighteen, I had developed into a teenager, who had a great body, but no confidence where girls were concerned.

My best friend was Alan and he lived about a mile from me in a large house in a much better neighbourhood than mine.

During term time we spent a lot of time together at school, but in the school holidays we sometimes found it difficult to meet up, because he was shipped off to stay at his auntie’s in Canterbury while his parents worked full time.

However, in that summer I was invited round to his house at the start of the holidays for 3 days before they all went off to Cornwall for their two week vacation.

With the usual warnings from my mum about ‘behaving myself’, I was delivered to his house with my bag of clean clothes and washing stuff.

Greeted by his mum, I briefly acknowledged her, before Alan took me upstairs to his room with its twin beds. I knew the house well from previous visits, but didn’t know that his aunt Jackie, from Canterbury, was staying for a few days. We rushed past her on the landing as we sought refuge in his room. But I did have time to register that she was a shapely blonde, a year or two younger than Alan’s mum, and just as attractive.

Alan told me we’d be introduced properly at tea, and, anyway, she would be ‘looking after’ me tomorrow morning, while he was being taken by his mum to a ‘work experience’ interview in the west end of London. It was something that had come up at short notice.

The rest of the afternoon passed quickly, and when the four of us sat down to tea I found I was sitting opposite Jackie.

She was quite amusing in an irreverent sort of way. Much to the apparent disapproval of her older sister, she constantly made sexual innuendoes about anything, and everything. Both Alan and I found it refreshing, because we were still treated As though we were much younger by our respective parents.

Jackie had large blue eyes, ample breasts and shapely thighs, shown off to advantage in her mini-skirt. My eyes kept sneaking glances in her direction throughout tea. It was one of those ‘glances’ that Jackie noticed, and when I looked at her again, she held my stare and I blushed cherry red.

For the rest of tea I avoided looking in Jackie’s direction, but when we’d finished eating, and Alan and I were anxious to return to our room, she made a point of remarking, “Tom, don’t keep Alan up too late, he has an early start in the morning. And I’ll let you sleep in in the morning, there’s no hurry for either of us.”

Alan and I amused ourselves for the rest of the evening, until it was time for bed, rather earlier than we both wanted, but Alan had to be up to catch an early train with his mum.

I slept well, and only muttered a muffled, “goodbye and good luck,” to Alan from under the bedclothes as he left to go downstairs. I must have then drifted back to sleep, and the next thing I was vaguely conscious of was a toilet flushing and someone moving about along the corridor. Şirinevler escort

Of course, Aunt Jackie was left behind to ‘look after’ me for the morning.

I lay there in that semi conscious state we all enjoy if we have nothing immediate to get up for. My mind drifted, and I was aware of being semi-erect, which had seemed a regular occurrence throughout my teen years. I was thinking of Aunt Jackie and the idea of a mature woman with her body, and whether she enjoyed sex. She was divorced and maybe she hadn’t had sex for a long time. Did she have a boyfriend?

I found myself squeezing my cock and it becoming harder. In fact it was very hard.

I strained my hearing to see if I could work out whether Jackie had gone downstairs, or was still in her room. I didn’t want to be caught wanking.

I decided it was ok, and pushed the bedclothes and my pyjama bottoms down. My cock stood upright, and I slowly slid my hand up and down the shaft. I closed my eyes and my hand moved faster. It was always a mental decision to slowly build, or to quickly release the sexual tension. I remember this was an urgent need. My hand was gripping the shaft firmly, but each rise and fall it rubbed the sensitive head, and in just a minute or two a jet of semen spurted into the air and backwards onto my stomach, followed by another, and another. The release was so good and I lay there, the rest of my ejaculate oozing over my thumb and pubic hair.

Reaching for my handkerchief, I heard the sound of feet passing the door, which Alan had left ajar.

Had Jackie heard me wanking? Had she heard the inevitable grunt I had uttered as I came? Indeed had she been watching through the gap in the door?

Of course, these were teenage fantasy thoughts, and she had probably been totally unaware, and unconcerned.

I quickly cleaned away the evidence of my wank session and got out of bed. I realised that Jackie was showering in the bathroom, and so I waited until she had padded her way back to her room, before gathering my washstuff and towel and peering round the door to see if it was clear.

I walked quickly to the bathroom, passing Jackie’s bedroom door, noticing it too was ajar, but I kept my eyes straight ahead and I knew I needed that shower.

At eighteen, although it may seem strange these days, I was still less than comfortable with girls, let alone older women that I barely knew. But teen boys have vivid fantasies, mostly that don’t come true. I was very much out of my comfort zone, but somehow enjoying the apparent thrill of it all.

I showered, stared at myself in the full length mirror and felt refreshed. Wrapping the towel around my waist I made my way back to my room. On the way, I slowed as I passed Jackie’s bedroom door. It was partly open, and I saw in the mirrored wardrobe doors a reflection of Jackie sitting on a stool in front of the dressing table drying her hair.

I couldn’t help taking a step back to get a better view. She was only dressed in a bra and panties; a cerise colour. I just stood frozen to the spot taking it all in. I was trying not to move, not to breathe, not to make a sound.

But she had seen a movement in the double reflection of dressing table and wardrobe mirrors.

“Tom, naughty boy!” Jackie Şirinevler escort bayan called out almost mockingly.

I’m not sure what I replied. A stammering, muttered apology. Something like “I’m so sorry, I didn’t mean……” I didn’t finish the sentence.

“Hey, don’t be a silly boy, come back here,” as I walked on quickly down the corridor.

I had frozen in mid stride again.

“It’s ok, I really didn’t mean to spy,” I garbled.

“I said come back here. I won’t bite,” Jackie’s voice was assertive.

I slowly turned, clutching my towel around my waist and my wash bag under my arm.

As I got to the door, she opened it wide and stood there in nothing but her bra and panties. I must have been open mouthed, and probably blushing, and not knowing where to look.

“Don’t be silly and come in. The house is empty. It’s a good chance to get to know one of Alan’s friends.”

I slowly moved inside the bedroom. It smelt like a totally feminine room. The smell of perfume, there were so many dresses, make up items, brushes, shoes all around.

The bed was dishevelled from when she had got up.

Jackie pulled the bedsheets roughly back into position and sat on the bedspread.

Almost inspecting me she asked if I was nervous, a strange question it seemed at the time but I said, “yes.”

I remember her saying, “well don’t be. You are a grown man. I can see that.”

It was only then, that I could feel my cock beginning to press against the towel wrapped around me, and realised her meaning.

Jackie beckoned me closer and told me to sit on the bed. There I was sitting just a few inches from this semi naked woman, not being able to take my eyes away from her cleavage, her thighs, her luscious lips.

Jackie, of course, realised this, and stared at me with her saucer like blue eyes. Her mouth pouted, and there was a half smile that would melt icebergs.

The moment of understanding had arrived, and it was Jackie who had long decided that my apparent innocence was going to be a thing of the past.

“Tell me Tom, do you like my body?”

I blushed deeply. “Of course I do Jackie.”

Saying her name out loud seemed to embolden me, and I clumsily added, “you’re terrific.”

“Then let me show you more,” and reaching behind her, she unclipped her bra, letting it fall into her lap, revealing two ample breasts and two pert, pink nipples.

Reaching forward Jackie took my hand and placed my palm onto the nearest breast.

I held my breath feeling the softness of her skin and the hardness of her nipple.

Her hand dropped down and rested in my lap squeezing my cock through the towelling.

“My word Tom, you’re not a boy any longer!”

Standing up, Jackie pressed her breasts into my face. I managed to take a nipple in my mouth, but almost as soon as I’d started to suck gently, she lowered herself to her knees in front of me, and kissed me probing into my mouth with her tongue. I was in heaven.

Her hands pulled the towel apart, and as my cock stood to attention, she lowered her head and I felt a sensation that was so new to me.

Her head moved slowly up and down below my chin. I heard myself gasping, and moaning, and wasn’t really sure what to do next. I was glad I escort şirinevler had enough self control after my wank in bed that I wasn’t going to cum quickly. But I couldn’t last forever.

Just as my resistance was slipping away Jackie stood up. She slid her panties down right in front of me, revealing a closely clipped pubic area that seemed to emanate heat. She was in control, and with a shove she pushed me back on the bed and climbed astride me, with a knee on either side of my hips. Reaching behind her, she lowered her body down and I felt myself enter her wet pussy. Her eyes closed, as I looked up at her face and I heard her groan “oh fuck.”

Her hips ground down against me, rotating round and round. She started to almost gurgle and to breathe faster, the gasping became louder, and I knew I was going to cum.

I remember gripping her thighs and watching her breasts swinging above my face.

I couldn’t hold on. The first spurt must have triggered her orgasm. My cock was jerking and her pussy seemed to grow very wet. I could feel a wetness soaking my balls, as she shouted out “Jesus”….”fuck, fuck, fuck.”

I felt the last of my spunk seeping out inside her, and she collapsed onto my chest

“Was that really your first time?” Jackie whispered.

“Yes I replied, and I’m glad it was you.”

We fell apart, and we both were realising what we had done.

Then the phone in Alan’s parents bedroom started ringing.

Jackie quickly went and answered it. It was her sister checking if things were ok, and saying that she and Alan would be home by 1pm.

When she returned I noticed it was just after 10am, and we were still glowing with what had happened between us.

Jackie started to say it shouldn’t have happened, and was apologising until I said that no one would ever know. It was our secret. Strangely, she kissed me on the cheek, and we both got dressed and went down to have breakfast.

The conversation was surprisingly polite, but there was an underlying electricity. I had lost my virginity to this much older woman, but I felt so confident and emboldened.

Breakfast finished, we set about washing up. Jackie at the sink and me with the tea towel. I kept taking the plates from the draining board, and having dried them, placed them on the Welsh Dresser. As I walked back each time to collect the next plate, I stared at Jackie’s ass, moving from side to side as she washed the dishes. I looked at the clock. There were still two hours before Alan and his mum would get back home.

As I placed the last plate down, I walked over to Jackie, and pressing myself against her ass, I reached round and cupped her breasts, one in each hand.

Kissing her neck I heard her say, “no we mustn’t.”

But I was in control now. I knew she didn’t mean it.

My cock was rampant again. I unzipped myself and slid her mini skirt up. I pulled her panties aside, and as she bent over the sink, I slid into her again.

I remember thinking that this was crazy. Here I was fucking a friends auntie over the draining board in front of the kitchen window for the second time in an hour.

Jackie was starting to make her panting sounds again and saying, “don’t stop Tom….don’t cum yet.”

The next half hour, (was it half an hour? I can’t remember now) was a blur. We moved into the lounge, first on the sofa, then on the carpet. Me on top, her on top, until I emptied myself again.

And so that was my first intercourse.

We never met again, I lost touch with Alan and his family.

But Auntie Jackie will remain a part of me forever.

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