I suppose it started when my Mom caught me stealing a pair of her silk panties and stockings from the linen basket. I was nineteen when she caught me and I'd got into the habit of taking a pair of her panties and sniffing the gusset as I wrapped a stocking around my cock and wanked. She caught me coming out of the bathroom, one of her stockings hanging out of the pocket of my bathrobe.
I thought that she would explode. I mean, what woman would be pleased to find her nineteen year old son masturbating into her stockings while he sniffed her panties? I did not realise that Mom had guessed wrong when she saw me with her stockings. I wanted to smell her pussy on the material; she thought I wanted to wear them.
"Well!" Mom snapped, "If you're going to steal them, you had better put them on."
I could see that she was really annoyed, so I said nothing, just slid the silky material up my legs and over my cock and balls. I started to close my bathrobe, but Mom lapped my hands away and made me stand there, with my bathrobe open, while she inspected the pink silk, covering me. Then she pulled her stockings out of the pocket of my robe and threw them at me, ordering me to put them on.
I could not help getting turned on by the feel of the smooth silk on my legs and over my ass and balls. My cock twitched inside Mom's panties and she just looked at me with one eyebrow raised a little. I could see the faraway look in her eyes that meant she was thinking deeply.
"Go to your room and wait while I decide what to do with you." she ordered.
I went into my room and sat on the edge of my bed. My cock was hard and throbbing and I desperately wanted to reach inside the panties and take hold of it but I dare not. I knew that, with my cock so hard and sensitive, one touch would make me blow my load into Mom's panties and that would make her furious. I tried all sorts of things to distract myself from the ache in my balls and cock but it just seemed to grow harder and more sensitive with every second that passed.
After a few minutes, I heard the front door open and voices from downstairs. I recognise Mom's voice, even though I could not tell what she was saying, but even though the other voice was familiar, I could not put a name or face to it. The voices carried on for almost half an hour, while I waited anxiously. I felt sure that I knew the other voice but, no matter how I wracked my brain I could not identify the owner.
The voices stopped and I heard movement downstairs, followed by two sets of footsteps on the stairs. I recognised Mom's light tread instantly, but I could not work out who was with her. One set of footsteps stopped at the top of the stairs and Mom continued on, into my room. Mom had been wearing only her bathrobe earlier, when she caught me in the bathroom, but now she had changed into a denim dress, that buttoned down the front. She was wearing hose and pumps with a two inch heel, but I had no idea what else she might have been wearing underneath. She stood in the doorway, her hands clasped behind her back and waited until I stood up. She looked down at my cock, pushing against the silky material of her panties and tutted when she saw the damp stain where a drop of pre-cum had leaked out.
"You can't even keep my panties clean." Mom snapped, "Well I've decided what I'm going to do with you. Take your robe off and get on your knees"
Numbly, I obeyed, kneeling with my back straight and my head hung, looking at the floor. I heard the other set of footsteps on the landing, then coming through the doorway. I kept my head down and all I could see was a pair of man's shoes and the cuffs of a pair of dark grey slacks. The sound of a zipper being pulled down was loud in the room and, with a rustle of cloth, the pants dropped around the shoes.
"Lift your head, you disgusting creature." Mom commanded, sternly.
I did as I was told and looked up to find Derek from down the street looking down at me. He was a head teacher who had taken early retirement when he had inherited a large sum of money. He lived on his own and there had been rumours about him but nothing provable. Now I could see his boxer shorts tented by a long, thick cock.
"Get his cock out and suck it." Mom said, "If you want to dress like a woman you had better learn to please a man."
I pulled his boxers down over his cock, acutely aware of the smell of him. The head of his cock slapped against my cheek, as it sprang free of the waistband of his shorts. His cock was hard and swollen, almost pulsing with the blood that was surging through it. Nervously, I opened my mouth and reached up to grasp the base of his cock and guide the head between my lips. Derek thrust his hips forwards, forcing the head of his cock to the back of my mouth.
Slowly I ran my tongue all over the hard meat of his cock, covering it with my spit. I could taste the sweetness of his pre-cum as he worked his cock in and out of my mouth, pushing deeper with each stroke until my eyes watered and I gagged as the head pushed to the back of my throat. Spittle ran down my chin and dripped onto my chest as tears left streaks on my cheeks. Mom whispered in Derek's ear and he stepped back, pulling his cock roughly out of my mouth.
"Stand up and turn to face your bed." Mom ordered me, "Now bend over."
