I got onto the bed and did what I was told. The tv was playing a porn movie and Debbie told me to start wanking myself off. I was trying to get hard again when she walked in and said this was not good enough and instructed me to stand in front of the bed and touch my toes. I did this quickly and just as quickly, she strapped my writs to my ankles leaving me bent over helplessly. She took her cane she used on me last time and announced that a good caning after the paddle should wake my lazy cock up a little. Just hearing this caused a feeling of dread but amazingly, my dick was already respond... Continue»
As my parents were divorced, I used to visit my mom once a month at the hotel she managed up the coast and normally my dad took and fetched me at the end of the two days. One weekend I went and her friend Debbie was visiting her as well. I was 17 at the time and she must have been about 32 or so. I had known her quite some time so was pretty comfortable around her. She was a bit plump but had a nice face and the most beautiful feet I had ever seen and she often caught me staring at them. On the Saturday night she and my mom who had the night off were going to go out and I was going to stay in the room and watch tv. My mom showered and got changed and came out of the bathroom fully dressed. Debbie went in and after showering came out with a towel around her while I was sitting on the bed. My mom had gone to reception to sort out a few details so we were alone. To my complete surprise, she dropped the towel on the floor while her back was turned to me and bent over to pull her panties on and I got an eyeful of her gorgeous hairy pussy.she turned around and put her bra on and I just stared at her lovely plump tits while she looked me straight in the eye with a knowing look and a small smile. Needless to say, I had the Hardon of a lifetime while they went out and while they were out, had a few intense jerk off sessions.
At the end of Sunday my dad phoned to ask if Debbie could bring me home as he was having car trouble. While we were driving, home Debbie asked if we could stop at her place so she could get changed to go out that night. She had a small cottage she rented on a large property. When we arrived she told me she just wanted to take a quick bath and would I like to watch a video while I waited which was no problem for me until it started ( quite a hot porno movie with anal sex and everything) when she came out she said the bat water was still hot and I should bat to get the salt water off me from swimming in the ocean. Again no problem and I took a bath. She left my shorts on the pedestal for me to put on after my bath. When I came through to the bedroom I got quite a shock when I saw her. She was wearing a black corset, stockings, panties and bra but what got my cock really hard were the leather thigh boots she had on. Debbie was always very sweet to me but her voice was quite different now, very authorative and strict. She told me to take my shorts off and lie on the bed with my legs open. I was taken aback and was a bit scared but excited as well so did what I was told. She put the movie back on and told me to start masturbating while she went to the bathroom to get something. I was very embarrassed but the movie got me going and I was soon wanking like crazy. She came back into the room and told me she wanted to see come squirt out of my cock NOW or I would regret it. Well I couldn't come immediately so after about ten seconds she ordered me to stop which I did. Debbie then told me to stand up while she piled about five pillows on the middle of the bed and told me to lie down on them which basically pushed my bum in the air. While I was lying face down, she quickly handcuffed me behind my back an tied my ankles to the corners of the bed whil telling me I would be getting the hiding of my life. She started with her hand which stung but was pleasurable but then pulled out a thick belt which she lambasted my ass with I was squirming and so she took a strap out of her drawer which went around the small of my back holding me firmly and as I was making noise she put a ball gag on my mouth. I must have got about thirty strokes of the belt and was in tears so she stopped an caressed my burning ass cheeks for a few minutes but then got up and pulled out a long thick rattan cane. She said to me that if I could take twelve of the best from her I could fuck her as many times as I wanted which I tearfully agreed to. They were twelve strokes from hell six from each side and my bum looked like red bleeding train tracks. After she untied me, she was very soft and sweet and let me take off all of her lingerie while she rubbed some cooling lotion on my butt which felt great. I left the boots and stockings for last and peeled them off her legs and feet while smelling them. She asked if I wanted to suck her toes and I went to it with relish and the were delicious ! we were both naked now Anaheim was straddled over my face so I started to lick her pussy which I found had been shaved with a small triangle of hair on top but the lips were smooth. This was incredible and I licked and sucked like mad. While I was doing this, I felt soft lips on my cock and her tongue lick the hole on the tip gently which nearly made me come so she quickly took out a syringe with a small needle and injected the base of my penis with some liquid. I got a fright when I saw it but it was done so fast it was over before I even fel the pain. She then gently started wanking me off for a few minutes and my cock just kept getting bugger and rock hard (sore even) " now you're ready for a real fucking and if I don't come at least five times, you'll get another hiding" I was amazed by my new hardon and she sucked it off for at least five minutes without me coming. Debbie then climbed up onto my cock and started riding gently while kissing me and the feeling of myself deep inside her tight elastic and hot wet cunt nearly drove me mad ! We started fucking faster but her strokes weren't so deep and I felt her shudder and groan twice in that position before she lay on he back with me over her but also not allowing me to fuck he too deep and to push my knob up toward her belly button. I did this an all of a sudden she squeaked and some kind of clear liquid squirted out of her pussy that wasn't pee but was thin and sticky but ha d a strange but nice smell and taste. I fucked her doggy style for about 15 minutes and she came twice again. Debbie looked very happy and relaxed and said I was to get a special reward. She made me lie flat on the bed on my back while she got a tube of clear jelly and put some on my throbbing cock she also smeared a little bit on her asshole. She tol me to sit up on my elbows and watch what happened next. She was facing away from me as she sat down on my dick an in the mirror, I saw my cock slowly sink into her asshole until it was all the way in up to my balls. This was already something that I had always wanted to try and she started moving up and down on my cock with full strokes while she fingered her cunt it was so warm and tight that I felt the most huge orgasm build up and tried to pull out but she pushed down and said she wanted to feel the come squirt up her ass which I did literally in buckets! When I pulled out her ass started dribbling a lot of come which we had to keep wiping away for a while. I was still hard and then fucked her swollen pussy sideways gently until she came again and so did I .
After we got dressed and she took me home telling me not to say anything to my parents as there were more things we could do in the future which I didn't so I have a couple more hot encounters to tell of next time !