Aunt Dorothy Takes My Virginity (Diary, Incest, Mature)

Aunt Dorothy Takes My Virginity

Aunt Dorothy isn't my real aunt. She's my mum's best friend and lives next door to us, my two arsehole brothers and me were brought up as kids calling her aunt, just as we did with all of mums friends.

Aunt Dorothy is 36 years old and she's married to 'uncle Ron' who is 19 years older than her, they have no children. Uncle Ron works in the coal mines with my Dad and when Ron isn't at work he'd be getting drunk in the local working men's club. My two brothers are both older than me and spend most of their time telling me how much they hate me, they hit me and mentally and verbally abuse me all the time, their favourite insult is to mock me for being a virgin, all this resulted in me being very down trodden, depressed, shy and geeky. I'm quite small and very thin, even though I'm 18 I look a lot younger.

During the long hot summer of 1976 with both my parents at work Aunt Dorothy would keep an eye on me and my brothers. Most days started the same, we were quiet but once they got bored my brothers would entertain themselves by picking on me.

Aunt Dorothy would hear the commotion from next door and come around to sort us out, this usually ended with her taking me round to her house and I'd spend the day with her. Aunt Dorothy seems to enjoy having me around as she likes to mother me, I think I'm the child she always yearned for. She is always smart and wears make up most of the time, she's very pretty, she has short jet black hair and beautiful brown eyes, she is a little curvy and has a big bust. She cuddles me a lot and pulls my face into her generous cleavage which I secretly enjoy.

Aunt Dorothy is very flirtatious and would often 'accidentally' flash me. I spent many hours looking down her top and up her skirt when we I could and I often got a glimpse of her nipples as she sometimes went braless and they would stick out really hard beneath her blouse or t shirt. She would lean forward deliberately letting her tits fall out and pretending it was an accident.

She would also lay on the sofa with me next to her and open her legs letting me see all the way up to her panties, I would stare and she would watch me but not close her legs. One time she caught me staring and said "do you like that Paul?"

"Yes, it looks nice" I replied.

She pulled her skirt up to her waist and beckoned me to her, she pulled me on top of her and hugged me tight, my crotch was pressed against her pussy region and she put her hands on my arse and pulled my groin tightly into her. She moved me up and down rubbing her pussy against my cock and I felt my cock hardening, "that's a good boy" she said. I'm very inexperienced sexually and never even kissed a girl properly, so this felt very exciting to me and I just went along with it. After about 5 minutes of this Aunt Dorothy said "it's so hot today, I'm going upstairs to change into something cooler."

"Ok." I replied and sat on the sofa.

"Come with me, help me choose something."

Aunt Dorothy pulled her skirt back down from her waist and took my hand and we went upstairs.

She led me into her bedroom and immediately she took off her top and her skirt, then instead of looking for some cooler clothes she laid down on the bed. Next she patted the space on the bed beside her "come on get on here with me."

I nervously got on the bed and laid beside aunt Dorothy "why don't you take your clothes off too." She said.

I removed my t shirt and kept on my shorts.

"Those too, take them off." She said as she pointed to my shorts.

I took them off and she pulled me on top of her into the same position we were downstairs. Her legs were wide open and my cock was hardening as it pressed against her panty clad pussy, my face was directly in front of her boobs. Aunt Dorothy pulled my head into her cleavage and hugged me tightly. I could feel her grinding her pussy against my cock that was really hard now, she was breathing very heavy, "are you ok?" I asked, concerned that she was ill.

"Oh yes, I'm fine how are you?"

"I'm ok." I answered as my face disappeared into her slightly sweaty cleavage. I was nervous and didn't know what to do. Aunt Dorothy moved a little and gently pushed me off her and I laid beside her once again.

She sat up slightly and removed her bra, "that's better." She said as she laid back down, her big boobs wobbled as she moved.

I sat up and stared intently at her boobs, "do you want to touch them?" Before I could answer she took my hand and placed it on her boobs and said "play with them."

I stroked them and they felt amazing, they were soft yet firm and her nipples were very hard.

"Lay down Paul." Said aunt Dorothy, I done as I was told and she manoeuvred herself into a position where she was leaning over me, she leaned forward and placed one of her tits on my lips, her hard nipple was between my lips "kiss them and suck them."

I reached up and held her big tit with both hands and sucked on her nipple like a starving baby, aunt Dorothy was stroking my chest and belly all the time I was sucking. I could feel my cock was still hard and could sense a wet patch in my pants.

She pulled her tit from my mouth, "how was that?" She asked.

"I loved it." I replied.

"Do you want to carry on? I can teach you everything about sex, but it must be our secret. Nobody must ever know."

"Yes, yes please, I want you to teach me everything. Nobody will know, I'll keep our secret safe I promise."

"Ok, now close your eyes."

I closed my eyes and felt aunt Dorothy's lips on mine. She kissed me for a few seconds then said "now I'll show you how to kiss properly like lovers kiss."

She told me to open my mouth and once again our lips met, this time it was different I could feel her moving her head and her tongue was touching my lips and going into my mouth, she broke the kiss "how did that feel?" She asked.

"Amazing." I replied.

"Ok, now I'll kiss you again, but do it back to me, use your tongue too."

Our lips met and I kissed aunt Dorothy just as she asked, I'd never felt such passion and didn't want it to end. I could feel her heavy boobs on my bare chest as we kissed. My cock was rock hard and leaking pre cum and trying to burst through my tight pants.

I desperately wanted her to grab my cock but she didn't, and I was too shy to say anything. She was my sex teacher and I needed to be patient.

Aunt Dorothy broke away from kissing my lips and started kissing my chest, it tickled a little but it was nice.

Suddenly she stopped and laid down on the bed, "are you sure you want to carry on doing this?" She asked.

"Oh yes, absolutely, I love it."

"Will you do anything I ask of you?"


Aunt Dorothy put my hand on her chest and said "play with my boobs again, stroke them, squeeze them, kiss them, do anything you've ever wanted to do with them, get used to how they feel, from now on they are yours, enjoy them.

It felt like the best present ever, I'd often fantasised about her big boobs, now I have them to do what I want with.

As I caressed them Aunt Dorothy was making appreciative noises and telling me what she liked, I leaned forward and licked her already hard nipples and sucked on them, "oh yes, that's a good boy keep sucking." She said as I saw her hand go between her legs, she was wearing panties and I watched as she rubbed her pussy through the thin material. I could hear a wet noise coming from between her legs as I continued to suck and lick her nipples.

Suddenly aunt Dorothy stopped and yelled, I thought I'd hurt her but she smiled and grabbed my head and kissed me.

"Is everything okay?" I asked

"Mmmmmm yes baby, I've just had an orgasm, thanks to you."

She put her hand inside her panties and I could hear the wetness again, she pulled her hand out and two of her fingers were soaked in her juices, she rubbed the juice onto her nipple, "taste it, lick it all off." She said.

I was a bit hesitant but licked it anyway. It tasted like nothing else I'd ever tasted but I loved it. "Do you like it?" She asked.

"Yes aunt Dorothy it tastes nice."

"That's good, we're going to have so much fun."

Having gained a little confidence I leaned forward and kissed aunt Dorothy while caressing her boob. "Mmmm that was nice Paul, I've taught you well."

We laid on the bed talking, aunt Dorothy told me she hadn't had sex for a few years as uncle Ron had a heart condition and he'd lost interest in sex, she also said she knew about the problems I was having with my brothers and the names they were calling me. She said "I've heard them mock you for being a virgin, well that's going to change very soon."

Unfortunately we couldn't go any further, it was getting late in the afternoon and my mum was due home soon.

We got dressed and went downstairs, "come round again tomorrow any time after 08.30 and we can spend all day in bed." Said aunt Dorothy.

"Okay, I'll be here at 08.30 if that's alright." I replied eagerly.

Aunt Dorothy said goodbye then put her arms around my neck and gave me a long lingering kiss, I felt my cock hardening again and really needed to cum. We said goodbye and I jumped the small fence between our houses, I ran inside and up the stairs and locked myself in my bedroom.

I took off my t shirt quickly followed by my shorts and pants and laid down on the bed, I took hold of my hard cock and stroked it, I knew it wouldn't take long to cum as I'd been hard for hours.

Thoughts of my day with aunt Dorothy were running through my mind, I couldn't wait to see her pussy and the thought of it took me over the edge, my cock spurted stream after stream of warm cum all over my belly and chest. I'd never cum that much in my life.

I had some cum on my hand too, curiosity got the better of me, I'd loved the taste of aunt Dorothy's cum and decided to taste my own. I licked it off my hand and although it wasn't as tasty as aunt Dorothy's cum it was surprisingly okay.

I slept well that night and aunt Dorothy was the first thing on my mind as I woke. I still had over an hour before I could go round to see her. I knew this would be the day I would lose my virginity. I had a shower and a shave, but dressed similar to yesterday in a t shirt and shorts as I didn't want my brothers to notice I'd made an effort to go and see aunt Dorothy.

Finally the time came for me to leap the small fence and go and see aunt Dorothy. My heart was pounding and I was nervously excited, I knocked the door and walked into the kitchen. Aunt Dorothy was stood there waiting for me, she had a huge smile on her face, she smelled wonderful and looked absolutely beautiful as she held out her arms to hug me.

She was dressed in a satin dressing gown and showing a lot of cleavage. Usually we hug when we meet but this time was different as she tilted my face towards hers and we kissed, our tongues met and danced in each other's mouth. My cock hardened in seconds as I reached behind her and grabbed her soft pert arse. Aunt Dorothy felt my erect cock pushing against her, we stopped kissing and she said "mmmm you're eager Paul, let's go straight upstairs." She locked the door and led me upstairs to her bedroom.

We entered the bedroom and I closed the door, Aunt Dorothy was facing away from me I walked over to her and put my arms around her waist, my cock was pressing between the cheeks of her arse, she took my hands and placed them on her tits, she was wearing a bra and her tits felt amazing through her satin dressing gown.

As I fondled her tits aunt Dorothy undone the belt to her dressing gown and slid it off her shoulders. I stood away from her a little and it fell to the floor, she turned around to face me and I thought my cock was going to explode.

I was looking at the most beautiful sight I'd ever seen, aunt Dorothy was dressed in black stockings help up with a black and dark purple suspender belt with matching silk bra and panties.

The curtains were closed and the light was coming from a table lamp beside the bed, she looked like a goddess and I wanted her.

I stared at her open mouthed and speechless, she smiled and helped me undress, she removed my t shirt and shorts just like yesterday but today she went further and slid my pants down my legs exposing my hard cock. "Mmmm what a beautiful looking cock." She said as she licked her lips. My cock was only average size, I don't profess to be hung like a horse, but aunt Dorothy was happy with it so that gave me some confidence.

Aunt Dorothy held my hand and climbed onto the bed, I followed her and we laid on our side facing each other, "I want to teach you so much today, I hope you're ready." She said.

"I'm definitely ready." I replied.

She gently pushed me onto my back and kissed me from my neck all the way down my torso until she reached my hard cock. I felt her fingers wrap around it and slowly stroke it up and down, then I felt her warm wet mouth around my cock and I watched as she took the whole length into her throat. She moved her head up and down very slowly and licked and sucked all the way up and down my length.

"I want you to cum in my mouth when you are ready, let me taste you."

I was ready, "oh god aunt Dorothy, that feels amazing I'm going to cum now." I just let myself squirt every drop of cum I had into her mouth, she had her mouth tight around my shaft but there was so much cum that it was leaking from her lips.

She took my cock out of her mouth tilted her head back and swallowed all that was in her mouth, then using her fingers she wiped the rest from around her mouth and chin and swallowed that too.

Aunt Dorothy laid down next to me smiling, I was smiling too and caressed her boobs as we got our breath back. Her bra had a clip on the front so I undone it and released her boobs, I kissed licked and sucked on her perfect boobs, I liked how her large dark areoles were soft compared to the hardness of her nipples.

She took my hand opened her legs and placed my hand on her pussy, she still had her panties on but I could feel her pubic hair through the panties and she had quite a large bulge.Photos http://cpmlink.net/_b9AAA She guided my fingers up and down the length of her slit and I could feel her warm wet juices seeping through her panties. Then she put my fingers on a small hard lump, "that's my clit, rub it gently and it'll make me cum." She showed me how she liked it rubbed and I followed her instructions until she screamed "oh fuck, yes Paul that's the way baby."

I'd never heard aunt Dorothy swear and was a little shocked but she clasped her legs tightly shut trapping my hand against her pussy. Once she'd calmed down she released the grip on my hand and opened her legs, her panties were soaking wet but instead of taking them off she told me to get between her legs and lick her.

This was the closest I'd ever been to a pussy and the smell, the warmth and the wetness quickly spreading all over my face hardened my cock in seconds.

I could feel the softness of her stockings against my face as I licked her pussy through her panties, aunt Dorothy grabbed my head and held it in place as I licked hard against her clit, once again she screamed and had another orgasm.

I put my fingers in the waistband of her panties and began to pull them down slowly revealing the jet black pubic hair on her mound. I very slowly pulled them down as aunt Dorothy lifted up a little to help her panties slip down her arse, I exposed her wonderful pussy bit by bit and kissed each bit as it came into view. Her pubic hair was soaked in her juices and I licked it up hungrily. Finally in front of my face was a beautiful perfect wet hairy pussy, I'd fantasised about this sight for years and now here it was.

I'd tasted aunt Dorothy's juices yesterday and once already today through her panties, now I wanted to bury my face in her wet pussy, so that's exactly what I did. I French kissed her open pussy and buried my tongue deep inside her. "Oh my god Paul, are you sure you've never done this before." She said.

I didn't reply, I just kept licking and swallowing her juices. Savouring the taste of my first pussy, "suck on my clit baby." Aunt Dorothy demanded.

I didn't need telling twice and sucked and licked her beautiful jewel, "finger me too."

I put two fingers inside her wet gaping hole and pumped them in and out slowly. "That's right, a little faster." She said.

I sucked harder and fingered her faster and her thighs gripped my head like a vice as she cum on my face, I was soaked in her juices and once she released my head she grabbed me and pulled me towards her face, we kissed and she licked my face clean, "mmmm I love the taste of my pussy juices." Said aunt Dorothy.

"Me too." I replied.

My cock was rock hard and dripping pre cum, I was impatient to feel my cock inside aunt Dorothy's pussy.

I knew today was the day that I would lose my virginity and now it was about to happen. Aunt Dorothy got on top of me and started rubbing her soaking pussy up and down the length of my cock but not putting it inside her. I almost cum so I grabbed her and laid her down, kneeling between her open legs I grabbed my hard wet cock and put it at the entrance to her pussy.

I pushed but nothing happened as I struggled to find her entrance due to my inexperience so she took hold of it and guided it to the right spot, it went in quite easily because of our combined wetness. I thrust in and out of her and couldn't believe how amazing it felt. After a very short time I cum inside her and it was the best feeling I'd ever had in my life. We then laid on the bed and just laid there cuddling and talking and kissing.

After about an hours rest aunt Dorothy started to stroke my cock back to full hardness she gently pushed me over onto my back then she sat up and straddled me, her wet pussy was touching my hard cock and she was leaning ever so slightly forward making her tits hang away from her body, she moved slowly towards my face and let them hang just above my lips letting me kiss them, she swayed from side to side as I kissed each one in turn, she reached between her legs and grabbed my cock, then lifting herself just away from me she started rubbing the head of my cock between her pussy lips and up and down the length of her pussy, "it's my turn to cum now." She said and she rubbed herself against my cock until she yelled "oh fuck that's amazing," as her pussy oozed even more of her juices onto me.

Then she guided the head of my cock to the entrance to her pussy and slid slowly down onto my hard wet cock taking the full length inside her.

She slid her pussy up and down on my cock slowly at first before leaning on my chest with both her hands and riding me faster and faster until I could take no more, I reached up and grabbed her heavy bouncing tits as I let my cock uncontrollably burst it's full load deep inside her, aunt Dorothy smiled at me as I was pumping every last drop into her and my cock felt tender every time she moved, I thought that was it, but she had other ideas, she sat upright and started to ride my cock again, luckily I was still hard, then she rubbed her clit as she fucked me until she screamed and I felt her pussy pulsating around my cock.

I begged her to let me cum again and I could feel the wetness dripping down my shaft and balls and forming a large damp patch on the bed. Each time aunt Dorothy could feel I was about to cum she stopped riding my cock and waited a few seconds for it to calm down. Finally she climbed off me and sucked my cock licking our combined juices from my cock, balls and anywhere else on my body she could find it, then she gripped my cock put her mouth over the end and with slow soft yet firm strokes she let me cum, as I cum she closed her mouth around my cock and I could feel every pulsating load shoot into her mouth, I'd never cum so much in my life but she swallowed almost every drop except for a bit that had escaped and was dripping down her chin. My cock was very sore now and aunt Dorothy finally released her grip, she smiled at me then using her finger she wiped the last drop of cum from her chin and licked it clean.

Once again we laid together on her bed, we were both smiling, "how do you feel?" Asked aunt Dorothy.

"Amazing, I loved every second of today, you're the best teacher ever." I replied.

"Oh your tuition has only just begun, if you want I will teach you much much more."

"Yes please aunt Dorothy, I'd love to learn more."

"Tonight I want you to think about anything you would like to do to me, or you would like me to do to you." Said aunt Dorothy.

"Okay, but you do that too as I'm happy to try anything."

It was late afternoon so we arranged to meet the next day at the same time.

As soon as I got home my brothers started on me as usual, one said "where've you been all day virgin boy?"

I didn't answer him, I just grinned and went upstairs for a shower. I felt amazing, discovering sex with a beautiful mature woman had given me confidence and I was hoping to take the lead a bit more tomorrow with aunt Dorothy.

I couldn't get aunt Dorothy out of my mind that evening, my mum said "have you got a girlfriend Paul? You seem to be in a dream world with a fixed smile on your face, that's only usually seen on someone that's in love."

"Don't be silly mum." I replied, but I was beginning to think the part about being in love was true. I was falling in love with aunt Dorothy.

About twenty minutes later aunt Dorothy called in to see mum, they went into the kitchen as they always do. I heard mum say to her "I think Paul's got a girlfriend he's going around in a dream world."

"Ahh bless him, he's such a sweetheart, it would be a very lucky girl to have him if you're right." Replied aunt Dorothy.

She stayed for about an hour, and each time I went into the kitchen I just wanted to grab her and hug her and kiss her. I couldn't wait to be with her again.

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