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."
I rested my hands on the bedclothes and bent over, my ass in the air with her panties stretched tightly over my cheeks. I felt her long, cool, fingers hooking into the waistband and pulling the material smoothly down to my knees. My cock sprang out, not as hard as when I had first put the panties on, but not yet soft, either. I felt hands on my ass, spreading the cheeks wide, almost hurting. Then I heard and felt spit splashing against my asshole.
Something hard pressed between my buttocks, stretching my tight asshole and I realised that Derek had started to push the head of his cock into my ass. At first I could just feel my ass being stretched, but then he thrust a little harder and I felt like my ass was being split in two. I moaned in pain, but mom and Derek ignored me. In fact Derek just grabbed my hips and pushed harder, forcing the head of his cock into my ass up to the ridge of his helmet. I tried to pull away from him, but he just held me still and pushed harder until he felt the tip of his cock forcing its way past my virgin sphincter. I moaned loudly as his cock invaded my ass, stretching it until I was sure that he would split me open. Derek's cock felt much bigger in my ass, than when he had fucked my mouth, and the pain made me sob like a baby. Derek just laughed and stabbed his cock harder and further up my tight passageway until his balls were squashed against my ass.
"He's a tight little slut." Derek grunted to Mom, "but I'm gonna fill his ass with my cum and that should loosen him up just right."
Before he had finished speaking, Derek rammed his cock, as hard as he could, into my ass and held it there. I could feel his cock jerking and spitting thick cum into my bowels as he grunted. His cock softened slowly and, while he slowly pulled back, I felt it slide out of my ass. I heard him pulling his pants back up and fastening the zipper, then his footsteps, as he made his way downstairs and out of the kitchen door. A slimy trail of warm cum trickled from my asshole, drying on my skin. Mom moved over and sat on the edge of my bed, close enough for me to detect a hint of the aroma that perfumed her panties. My cock twitched and swelled again as I closed my eyes, trying to stifle the moan of pain as my bruised and tender asshole contracted.
"That is your reward for stealing my clothes to wear." Mom told me, quietly.
"But I didn't wear them before, Mom." I protested.
"Then what did you do with them?" she asked.
I blushed and suddenly realised that she might prefer to think of me wearing her stockings and panties, rather than wrapping one around my cock and sniffing at the other. I gulped and suddenly got very interested in the pattern on the bedclothes. I could sense that she was getting impatient and so I looked at her and mumbled my answer.
"I used to sniff your panties and wrap your stocking around my cock." I blurted.
