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I have a few stories from a horrible boarding school I was at in the seventies. All queer and all true.
I was 14 and we had to skivvy for any prefect who chose us at the beginning of the term.
The one chose me was an arrogant arsehole, a bully and had a huge cock which he was very proud off. One day, he told me to get his socks which I had washed the previous day so I took the to his little room which prefects had, the rest of us having sleep in the long dorm. I opened the door to lob the socks in to find him reclined on his bed with an erection which I couldn’t avoid having a glance at.
I turned to leave and just before I shut the door he said “Hey man, you looked eh” I was pretty embarrassed but really pissed off with this arsehole so I went into the room and said “ Go on then, show me again then”
He was shocked and uncertain and had covered up his crotch with a pillow. “What’s the matter, gone all shy have you?” I was shitting myself but i took a couple of steps forward and yanked the pillow away and exposed his rapidly deflating cock.
“ Not so big now, is it?” I said looking at his cock and balls. He began to close his legs and cover up but something made me lean forward and take hold of his cock. He jumped but kept still so I began to wank him. He groaned as I sped up my strokes, his cock thickening and lengthening until he was at full mast.
His cock was so big I could have both hands on it and still have the whole head suck out. He didn’t take long to come, his spunk spurting up onto his chest and belly and over my fingers.
Without saying a word, I wiped my hands on his pillow and walked out.
Naturally, this became regular thing and his whole attitude towards me changed for the better.
I regret not trying to suck that monster cock, as I regret not sucking any of the beautiful boys I played with.
I was at boarding school a decade before you. My experience was horrid too, but while the other boys were bullies I enjoyed my relationship with our retired music master!! I visited him at his cottage many times for extra tuition.
He was a widower in his late sixties and he seduced me and we had sex!!
I’m glad you got some joy out of it. I’d like to know how an old bloke seduced you. Our teachers were all misfits and the regime encouraged bullying.
I had been cycling over to his cottage for about a month and he usually greeted me at his front door dressed formally, suit and tie etc, but this particular evening he was in his dressing gown. He apologised for looking so casual but explained that he'd not long had a shower and hadn't had time to get dressed.
We went in to the lounge where he had his piano and I sat on the stool, while he leaned over me to select a piece of music to play. His gown opened and I could see he was completely naked underneath! I couldn't take my eyes off his huge manhood, although I didn't realise it at the time it was semi-erect!!
We had the lesson as usual and afterwards our usual tea and cake while we sat on the sofa and again his gown drooped open exposing his naughtiness. I couldn't help myself, I put my teacup down and leaned over and clasped his manhood in my hand and not taking my eyes off his face. as I was cautious of him being angry.
He put his hands to my face and drew me nearer to him and kissed me so passionately and whispered "please be my little girl you darling boy"!!
That was how dear Graeme seduced me!!
What a lucky man he was. What a sweet story.
About a fortnight later, Graeme was kissing me when he asked me if I would wear some of his late wife's underwear, I wasn't sure but agreed to try and we went up to a bedroom. He took some things from a wardrobe and laid them on the bed and asked me to undress. We both stripped naked and he got a pair of knickers and helped me put them on. Oh! the feeling was incredible, they were so silky and lacy, then he handed me a petticoat and a bra and when I put them on I felt so feminine.
He took me by the hand and led me to the bed, he was so horny and erect and I felt so girly and little when he turned back the bedclothes and we got into bed together!! Graeme was so gentle and loving and I so enjoyed that experience with many more to follow!!
Please let me continue my story; Graeme was rather different with me when I was wearing his late wife's clothes, the way he looked at me, the way he kissed me, the way he fondled me, so gentle and unhurried!
We got into the habit of me dressing in the feminine underwear and a dress prior to the piano lesson and Graeme would wear his robe. He would stand behind me as I sat playing , pressing himself against me, I could feel his erect penis and I would turn around, open his robe and stroke and kiss his throbbing manhood he loved that!!
Once the music lesson finished, or even on occasion earlier, Graeme would take my hand and we'd go to the bedroom, I'd feel his hand up the dress caressing me naughtiness in the knickers as we climbed the stairs, then as he took off his robe in the bedroom I would take the dress off and we'd get into the bed and make love.
Graeme was so horny, I got to know exactly what he liked and I adored being his submissive girl and this activity being our special secret.
Soon I was tall enough to wear stockings and I found that so sexy, Graeme would kneel and fasten the clasps, nuzzling my erect naughtiness and licking me as I stepped into the silky knickers and he pulled them up and over my naughtiness and suspenders. He would caress my stockinged legs, his hands rubbing up and down pulling me onto his face for "our special intimacy" as he called it and sucking me to my ejaculation.
Our relationship lasted until I was 19 and Graeme passed away when I was at University. I believe that he really loved me as I inherited all his assets including the cottage in Somerset and I inherited a love of being feminine and have lived that way ever since!!
I had friend who liked lingerie although I never saw him in stockings and suspenders. I wish I had as I think they are very sexy. A really sexy story and I’m glad her loved you.
Thank you for your kind reply. I believe he grew to love me, and he awakened a part of me that was hidden. As an orphan I was brought up by an aunt and sent away to boarding school at the age of eleven. I was little and frightened, geeky and very shy, so the perfect target for the bullies.
Graeme gave me the care and love I so much craved, but his love also gave me strength!! Most of all academically strong and my size became an advantage in my late teens, in that I looked good as a teenage girl and I knew it!! Graeme would take me out as his granddaughter, where I would flirt with waiters and such like, which sometimes made Graeme jealous, but he soon got over that when I made a fuss of him when we got home.
I feel certain that I fulfilled a need in Graeme during his later life and he more than returned that kindness.