Annie Holder's House Pt. 03

The Tuesday and Wednesday passed without any sign that Annie wanted me to return for more punishment. Walking to college on Thursday morning I spotted the pair of black briefs in the landing window that signalled my return that evening.

When I arrived at four 'o' clock I opened the front door. On the previous Monday I had undressed on my own in the hallway and waited until I was called through. This time, Annie was waiting in the hall herself. In contrast to my two previous visits where she wore a dress, this time she was in a black, calf length dressing gown, closed with press studs at the front. Her legs were bare and she had slippers on her feet.

"Get here!" She ordered, "Turn around and get your arms up in the air. From now on you won't undress yourself, you'll come in and wait for me to strip you!"

I did as she ordered. She pulled off my sweatshirt and threw it down, followed by my T-shirt. My arms remained in the air as she stood behind me and ran her hands over my chest and stomach.

"Left foot back!" She ordered. I kept my arms in the air and lifted my foot. She pulled off my training shoe and sock together without unlacing the shoe and tossed them aside. The same happened with my right shoe and sock.

She reached around, undoing my belt, unfastening the button on my jeans and unzipping my fly. Before yanking down my jeans harshly. "Step out of them!" She ordered. I stepped forward as she grabbed and threw my jeans with one motion.

She slid her wrinkly hands inside the back of my briefs and yanked them down to my ankles. "Step out, turn around and keep your hands away from that little cock of yours!" She ordered. As I did so she flung my briefs towards my jeans on the floor.

She reached down cupping my balls in one hand and stroking my penis with the other. She gripped and withdrew my foreskin, saying, "That's it, now keep it pulled back."

She let go and told me to turn and face the living room door, drop my arms and stand straight.

She grabbed my penis again, this time running her gripped hand coarsely over my glans and shaft, masturbating me. "Let's get this tiddler hard shall we?" She cackled.

My penis rose to attention and I was sporting a full erection within seconds. She smiled and spoke, "That's it, you little bastard. Now when I say mush you get yourself through that door and stand facing the armchair!"

She paused, letting go of my penis. She slapped my buttocks. "Now, mush!"

I walked swiftly through Annie's living room and stood facing the armchair that had been positioned with her small coffee table beside it. Lots of items were laid out on the coffee table, but as I was aware of Annie watching me I faced the chair and looked forwards instead of examining them.

Annie strolled in and sat in the armchair. Eddie was nowhere to be seen. "I bet you've never been across someone's knee for a spanking!" Exclaimed Annie, "It's about time you did!" She pulled apart her dressing gown and parted her knees.

"Get over here now and don't put your weight on me, support yourself!" She ordered. I positioned myself and bent over her lap. She grabbed my penis and testicles, forcing them between her knees and closed her legs, trapping and squeezing my genitals. With my feet and hands on the floor I supported my weight as Annie pushed my head down and pulled my thighs forward to get my buttocks in the air.

She began to slap my buttocks with her right hand, one at a time, quite quickly and sharply. The slaps began to sting and my buttocks heated up with each one. She laughed to herself as she continued to strike my warmed up buttocks while she ground my penis and testicles between her lower thighs.

A good ten minutes passed, all the while Annie slapped away at my tender and sore ass cheeks, alternating between hard strokes with long intervals and sharp cracks repeated quickly. She pushed my head upwards with her left hand, "My hand is stinging now, stand up!" she ordered. I stood and watched as she retrieved a twelve-inch wooden ruler from the pile of things on the coffee table.

She whacked the ruler across the top of my semi erect penis twice, before tapping the underside of it, making it rise and drop. She passed the ruler into her left hand and began to masturbate me with her right hand, slowly but purposefully. "I bet you thought I'd have forgotten what to do with one of these didn't you?" she asked, as my penis hardened in her grip. "No Mistress." I gulped, aware once again of how easily aroused I was.

"Don't lie!" she cackled, "I know just how to treat this little worm!" She pulled my penis down, making me take up position over her lap again. This time she fed just my penis between her legs, letting my sac rest on her thigh. She opened and closed her legs a few times, squeezing it between them.

She took the ruler in her right hand and systematically began beating my buttocks with it, right-left-right-left continuing on as the heat built up in them and the stinging, burning pain spread up my back and down my legs.

Every time she pulled her hand back to begin, she relaxed her legs. Each time she struck she closed them hard, trapping and squeezing my penis between them. Despite the constantly fanned flames of pain in my buttocks my erection remained rock hard and as she struck me time and time again I felt like I would cum very soon. My balls were ready to erupt.

My breathing probably gave it away. Annie stopped and put the ruler down. "You're not supposed to be enjoying this, you little bastard!" she snapped. "Get off and kneel down in front of me!"

I did as she asked. She slapped my cheeks hard with the flat of her hands, left first then right. She looked me directly in the eyes. "When you stole my underwear off my clothes line you wanked over it didn't you?"

I didn't actually. It was more a dare and a joke with my friends. I guessed, though, that was not what she wanted to hear. I answered, "Yes Mistress," and looked downwards. She slapped my cheeks again, "Look at me you little shit!" She snapped. I directed my gaze at her face. "I'll give you a wanking lesson every Thursday now and it's one you won't forget!"

She picked up a pair of large panties from the table. "Not clean ones this time, ones I've been wearing!" She cackled, and pushed them under my nose. They smelled musty and pungent. She had probably worn them since Monday and taken them off before I arrived, hence her attire.

"Open your mouth!" She ordered. With my mouth open wide she pushed the panties inside, poking in with her finger. She pinched my lips shut and picked up a pair of tights from the table. These she pulled over my head so that the crotch was over my nose. She stretched and wrapped one leg around my head over my mouth, and the other over my eyes, tying each off.

The odour from the tights was every bit as pungent as that from her panties that now resided in my mouth. As I swallowed saliva I thought about it being mixed with the juices on her panties. I quickly pushed the thoughts away, concentrating on what I could partially see.

"Can you breathe?" She asked. I nodded. "Can you see?" she asked. I shook my head, although it wasn't the entire truth. I certainly could not see straight ahead but looking downwards I could see through the mesh of the tights almost clearly.

She instructed, pulled and pushed me into a position she was happy with, making me stand, my legs apart, straddling her legs and my erect penis pointing upwards at her face. My hands were to remain behind my back. Grasping each opposite elbow.

When I looked down I could not see her face but I could see her body from her chest to where I straddled her thighs. She picked up a tennis shoe lace from the table and wrapped it around my scrotum, between my penis and my balls. She looped it, pulling it tight, before tying it off with a double bow.

She placed a small towel over her thighs underneath where my penis stood, stil erect then picked up a small bottle of baby oil, opened it and poured a stream up my penis shaft from base to the tip of my glans. She put down the bottle quickly and grasped my penis with her right hand, obviously eager to start.

"I'm going to wank you now," she stated, "and I'm going to wank you properly, and hard. I'm going to wank you so hard and for so long it will be painful. You'll do one thing and one thing only!" She paused while she smoothed the oil over my penis. "You won't cum! If you feel like you are going to cum you stop yourself. You'll get no help from me, I'll keep wanking you until I think you've had enough and then some more." She paused again

"This will happen every Thursday now and don't think you'll help yourself by wanking yourself off before you get here because if you don't get it hard straight way you'll get a bigger beating and I might even ask Eddie to do it!"

She began to masturbate me, sliding her hand along my shaft quickly and smoothly. The urge to cum was almost immediate and I breathed deeply through my nose as my eyes widened. The odour from her tights filled my nostrils and reacted with the taste of her body fluids from her panties on my tongue. I fought hard not to explode as her hand slid deftly up and down, massaging my glans and sliding swiftly from tip to base and back along my penis.

Thoughts that she would slow or stop when her hand got tired were diminished as she switched between her right and left hands almost seamlessly, the relentless masturbation not even pausing as she did. I gasped against my pantie-gag as I desperately resisted the urge to blow my load. After what felt like an age but was probably about ten minutes my shaft and glans were burning and my balls had a dull ache that was getting worse as time moved on. I was still fully erect and Annie's hand was still gliding up and down my shaft at speed.

She stopped a while, pouring on a fresh coat of baby oil and wiping her hands. I had been looking straight ahead into the blindness afforded by the tights leg covering my eyes. As she started masturbating me again I looked down to see that her dressing gown was gaping open at her chest where she had undone two press studs and while she slid her right hand along my penis her left hand was inside her dressing gown. She was fondling her breasts!

How I didn't shoot my bolt at this point I don't know but unaware that I could see her she was playing with herself as she masturbated me. I willed her to open some more press studs so I could perhaps glimpse her breasts but as she changed hands she pulled her gown closed, leaving the two press studs open.

As I visibly gasped, she pulled open another two press studs further down and put her hand down into her own crotch. Her thighs parted, touching against mine as her hand moved inside her dressing gown. She moaned lightly, obviously trying to suppress the sound as she carried on her dual assault on my penis and her own nether regions. Whether she was rubbing her clitoris or inserting her fingers in her vagina I couldn't see, sadly but she was evidently enjoying herself.

As this continued her hand movements on my penis sometimes got erratic, though this didn't help my efforts not to ejaculate and my balls now ached agonisingly I was near delirious trying not to cum.

Annie's concentration was so intense that she didn't hear Eddie come in the front door and into the lounge behind me.

It was only when he spoke that she jumped back with a start, pulling her dressing gown together and pulling her hand out at speed. ""You still wanking him, Annie? You'll wear it out at this rate!" Eddie joked.

Annie stammered and coughed, embarrassed. "No more than he deserves!" She croaked, trying to maintain some composure. "Don't stop on my account," laughed Eddie, "I don't mind watching his balls turn blue!"

He stood at my side, "Bloody hell Annie, I've never see a cock that red, it looks like a stick of rhubarb! How long have you been wanking it?" He chortled. Annie looked towards the clock above her fireplace. "Over twenty minutes at least." She cackled, adding, "That's enough now, time he learned another lesson. Did you finish it?"

Eddie passed Annie something. She held it and looked at it in front of her. As she lowered it I saw that it was apiece of broom handle around eighteen inches long with graduated marks from around six inches from its tip to a handle around six inches from its base wrapped in grip tape like a tennis racquet. I knew immediately what they were going to do with it.

Annie removed the lace from my scrotum but the ache in my balls did not subside. She wrapped it tightly around the base of my throbbing, sore penis, the lace cutting into my erect flesh and burning as she pulled it tight and tied it off.

I was made to kneel. Annie removed the tights from my head before having me push the panties from my mouth with my tongue into her hand. I was made to stand. I noticed Annie adjusting her dressing gown as I did so, fastening the press studs and smoothing it down.

I was made to lie on my back on the bench I had been whipped on the previous Monday and to spread and bring up my legs, holding my calves with my hands. Annie knelt down and taking the bottle of baby oil she poured a stream over my penis and down between my buttocks.

Eddie watched, transfixed as Annie placed the bottle back on the table and picked up the length of broom handle. Annie grinned as she waved the wooden phallus in front of my face. She pointed at the first mark on it. "That's about the size of your little tiddler! We'll try that up your ass first shall we?"

She poked at my sphincter with the tip of the tool, applying pressure as my anus contracted involuntarily. Eddie shouted in my face, "Don't try and stop it going up your shitter, boy! It's going up there whatever you do!"

Annie laughed and pushed the tip of the tool in. Although only an inch or so in diameter it felt much wider and I gasped as it slid inside.

They both laughed, then Annie pushed the tool further up my anal passage. She carried on as my anus tried to contract eventually getting it so it seemed it was up inside my stomach. "That's only six inches," she told me, " Hardly in there!" My anal passage seemed stretched beyond belief as it coped with its new and uncomfortable visitor.

Annie pulled the tool out until its tip sat around half an inch in, and then pushed it in quicker this time. My mouth dropped open as the phallic shape pushed its way up my anal passage, seemingly into my bowels. She let it sit there for a few seconds then withdrew it quickly, pulling it right out this time.

My penis throbbed, still rigid and tied tightly at its base. Annie grabbed it and squeezed it hard, digging her fingers into the flesh of my shaft. She pointed my glans towards her and spat on it. "I half expected it to sizzle." She joked to Eddie, adding a question to him, "Do you want to watch or will Dot be expecting you back?"

"I'll watch you work on his ass hole then get back," replied Eddie. Annie nodded before spitting on the rounded end of the broom handle then dribbling spittle from her mouth onto it.

She positioned it against my anus, twisting the tip in my sphincter. With one huge thrust she pushed it inside as far as it had penetrated before.

She pulled it out slowly then thrust it in again even harder. My eyes rolled with the agony as it pushed deeper into my rectum than it had before. This time she withdrew it sharply leaving me in more agony as my anal passage contracted, pain increasing as it coped with its unwelcome intruder's movements.

Annie grabbed my penis and squeezed as she inserted the rounded end of the handle again, pushing it in fully. "Right you little bastard, let's get started!" She panted in excitement and began a fast, hard, rhythmic thrust and pull. The wooden pole slid up and down my anal passage as I choked and gasped through the sheer agony of it. Annie showed me no mercy and they both laughed with sheer glee at the pain it caused me.

For fifteen long minutes I suffered the humiliating and painful experience of Annie thrusting the wooden pole up and down my anal passage, thankfully breaking off for the addition of more baby oil as lubricant from time to time as she felt dry resistance.

All the time that one hand was thrusting the pole up my rectum, her free hand was squeezing, twisting or yanking my penis. For minutes on end she pressed her thumbnail into my glans. It was all I could manage not to cry out in pain. With the lace tied at the base of my penis it stayed erect and throbbing.

Annie finally called a halt to it, saying that although she was enjoying seeing me suffer, her arms were a bit tired from wanking me for so long earlier.

As Annie finally withdrew the wooden phallus from my anus, Eddie beamed proudly, gloating about how red and swollen my sphincter was. "That's a proper work out up your shitpipe, boy! Your ass hole looks like a baboon's!" Annie laughed with him, adding, "Deeper, harder and for longer next week you little shit!"

I was made to stand, and Annie untied the lace, letting blood flow once again into my penis. It pounded and ached from its rough treatment. Annie didn't leave it alone though, insisting on masturbating me again. As she talked to Eddie she carried on vigorously pumping my foreskin backwards and forwards over my glans, stretching it down my shaft and off the tip with her wrinkly, bony fingers in a tight grip.

I could see Eddie's obvious erection through his trousers. In this state of arousal he seemed a little irrational, making a comment about taking me upstairs and reaming my ass. Annie seemed a bit on edge too, perhaps through some level of sexual arousal.

They began to bicker and Annie shouted at me to stand still and wait, as she ushered a reluctant Eddie into her hallway and closed the door. Though they talked in hushed tones it was obvious that they were arguing. Off phrases filtered through the door as voices were raised.

Eddie saying, "I don't see how that's worse than what you've been doing to him!" and Annie saying, "Don't make me out to be a liar, I haven't and it's none of your business if I had anyway!" The argument continued some while. They were still in the throes of it when they obviously decided that I shouldn't be left any longer and returned.

Annie said, resignedly, "Fine, do what you want, nothing to do with me," as she came through the door. Eddie replied pompously, "I will, don't worry. What I decide is none of your business!" He was red faced and panting. He pulled a small pill bottle from his pocket, shook out a tablet and popped it in his mouth without looking.

Annie came straight over and told me to bend over. "What are you going to do now?" asked Eddie. "What does it bloody look like I'm going to do? I'm going to slipper his ass!" snapped Annie.

"I thought your arms were supposed to be tired?" scoffed Eddie, adding, "Mind you I bet your legs aren't to tired to open!" in a mocking tone.

Annie didn't rise to his mocking, merely stating, "I thought you had to go now? Goodbye!"

Eddie shuffled to the door before turning around and asking calmly, "Are you sure you'll be all right on your own with him?" Annie reminded him that she had been absolutely fine on her own earlier before he arrived.

He addressed me before he left, telling me, "I'll be seeing you soon enough, boy!" He left, closing the doors as he went, dropping the latch on the front door as he exited.

Annie walked immediately to the front door and locked it, so that anyone from outside couldn't enter, even with a key.

She came over and made me stand up straight again. She took my balls in her right hand, massaging them around in my sac. "Are they aching?" she asked, squeezing them gently. "Yes Mistress," I replied. They were actually aching less now but were in agony earlier when I had been masturbated continuously and not allowed to cum.