Please leave comments good bad or indifferent. I am really interested in your critique.
This recollection is about a game I played with Pamela when we were in our mid-twenties. In most of our games we play as parent to child. With the naughty child being punished with a spanking in some form. But on this occasion Pamela wanted to play with both of us as adults and include sexual activity as part of the role-playing.
Another big difference is we would both be role-playing outside our natural preferences. Pamela likes being a bottom, the one being controlled and punished. Where I am happiest as a top, the one in charge and doling out the punishment.
There would be one other difference in that this is the first time we would be experimenting with bondage and using some sexual toys in our game. Pamela had set the scene; I would be her newly acquired sexual toy. She would be training me to serve her pleasure and to do this she would need some things to punish and bind me with. Also she had made some purchases that she informed would be a complete surprise.
So on Friday night I reported to my new mistress’s apartment ready for a night of servitude. I found a note for me taped to the door me to come in and go directly into the bathroom where I would find the outfit I was to change into. I entered the bathroom to find a loose fitting vest and a pair of the skimpiest underwear I had ever seen. Both were bright red and made out of satin. Where she had come up with them I had no idea but as I stripped to put them on I decided I was in for a very long night. I knew that Pamela had put some real preparation into this fantasy game and even though she was a sweet person could be quite ingenious and tough when she wanted to be.
The vest was fine it tied in the front and hung from my shoulders but when I slipped into the red satin underwear my balls and cock barely fit in the cup area and I could feel the cloth clinging around the cheeks of my ass. On the sink was another note next to a bottle of her favorite men’s cologne. The note read ‘Put a touch behind each ear, under each nipple, just under you belly button and under your balls’. Dressing her slave boy and perfuming him the way she wanted and I hadn’t even seen her yet.
After placing a touch of the cologne in the spots where she ordered me to I exited the bathroom and heard Pamela call from the living room. “Slave, come to your Mistress.”
Hurrying into the living room I knelt on the floor at Pamela’s feet and lowering my head to her feet said. “Yes Mistress.” And as agreed to earlier to help set the scene I continued. “I am a gift to you from your friend Janet.”
“Janet has good taste, I have been expecting you boy. Can you read?” Pamela says.
Not knowing where that question was leading I decide to answer honestly. “Yes Mistress.”
Pamela reached into a duffle bag sitting on the floor next to her and pulled out a thick leather dog collar. Attached to it was a tag and holding the collar in front of my face Pamela said. “Read the tag boy.”
“Yes Mistress.” And lifting my head from the floor I read the tag. “I belong to Pamela.”
Pamela again reaches in the bag pulled out a small brass lock. As She placed the collar around my neck I notice a pair of rings near where the buckle was and when the collar was in place I heard a distinctive click as she locked it in place.
Up till this point I was playing a game but the locking of the collar had a strange effect, all of a sudden I felt something around my neck that I could not remove. Pamela had made me her slave with the locking of the collar. A collar with a tag that said ‘I belong to Pamela’ for the whole world to read. She had dressed me in the manner she wished and I knelt at her feet waiting for her next command.
“Good, I think I’ll call you Todd.” Pamela said. “Yes, Todd sounds like an appropriate name for a pretty slave boy.”
God, she had just done it again. Not only was I collared she had named me. Even though this was my name the implications here were intense. She could have named me anything she wished. I don’t know if Pamela realized this but she so far she had made me feel me feel like a slave instead of a participant in a role-playing game.
Pamela stood up and said. “Pick up the duffle bag and follow me Todd.” As I tried to stand to follow her Pamela said. “You follow me by crawling, slave.” When I looked at the duffle bag she added.” Put the handle in your mouth and crawl behind your mistress.”
Knowing myself as a slave I leaned forward and grabbing the handle of the duffle bag with my teeth I began crawling behind my mistress. The duffle bag was bulky and weighed about ten pounds. It was not an easy chore keeping up with Pamela crawling and half carrying half dragging the duffle bag with my mouth.
Pamela led me to her bedroom door and as crawled past her into the room she reached down and swatted my ass a couple of times with her hand. “Move faster slave, I can see that what I have planned for you next is going to be necessary to get you more enthused in your serviced to me.”
“Yes mistress!” I said and tried to speed up my pace to please her.
Following me into the room Pamela took the duffle bag from me and pointed to tall wooden barstool standing at the foot of the bed. “Todd stand and bend over the stool.”
I stood and placed my hands on the stool seat and bent at the waste a little. Pamela again spanking my bottom with her hand said. “Lay your belly on the seat, stretch your hands down and grasp that cross bar next to the legs of the stool. Place your feet on the inside of the back legs of the stool, pressed tight up against them.”
I followed her instructions to the letter and said. “Yes Mistress, Sorry Mistress.” As I placed my hands and feet in the positions that Pamela had told me. I then that noticed at all four posts, tied to legs of the barstool, were lengths of rope.
Pamela laid the duffle bag on the floor in front of the stool right below where I was facing. Taking up one length of rope she wrapped it four or five times around my right leg securing it in place. She then proceeded to do the same to both of my hands and my other leg. She then unzipped the duffle bag and feeling around brought out another length of rope that she passed around my waist and the seat of the barstool and tied my tightly. I would not even be able to wiggle during whatever she planned to do to me.
Standing behind me Pamela lightly smacking my butt said. “All tied up Todd. I am going to soon be spanking this cute bottom of yours. I do this to all my new slaves first thing. I use it as a teaching tool.” Pamela kept chattering at me. “This way a new slave has no doubts that I will punish him any time I wish. I find it helps the new slave concentrate on the job of pleasing and obeying me.” She then grabbed the waistband of the underpants and pulled it upward giving me a wedgie but more importantly leaving the cheeks of my ass exposed and my cock and balls tightly bound up in the cloth.
“Please Mistress have mercy, I promise to serve you to the best of my abilities.” I claimed.
Reaching into her magic duffle bag Pamela pulled out a leather paddle. It had a wooden handle and a four-inch wide and ten-inch long rectangular striking surface. Where the hell did Pamela come up with this thing? I had no idea where one could buy a paddle like this. Pamela kept showing more resourcefulness and the further this game went the more I felt like a slave.
Pamela walked behind me and tapping me on the rear with the leather strap said. “Oh Todd you will serve me well, and it pleasures me now to discipline you. I want you to count the blows. I don’t know how many times I am going to hit you but keeping the count would be nice for me.”
“Yes Mistress.” And I tense up the ass cheeks in anticipation of the first blow.
‘Swish!’ ‘Crack!’ The leather bit into my ass. Oh God this was going to hurt. “Ouch! Please Mistress not so hard? N
umber One Mistress.”
‘Swoosh!’ ‘Swat!’ The paddle again struck me. The hit was not as hard as the last one. Thank God Pam was going to show some mercy. “Oww! Number Two Mistress.”
‘Whack!’ Another strike harder than the first. Pamela was not showing mercy instead she was upping the torture; I would have no idea how hard each blow would be. “Argh! Please Mistress.” I hollered out.
“Todd you ask for mercy but you can’t even follow simple instructions. Now count.” Pamela said sternly.
“Sorry Mistress, Please forgive me?” I begged. “Number Three Mistress.”
‘Smack!’ ‘Crack!’ ‘Swat!’ The punishment continued. With each ‘Strike!’ to my reddening ass I cried out in ‘Pain!’ and then counted the stroke. Pamela kept varying the hardness of each ‘Spank!’ to the point I had no idea how to prepare for the next stroke finally as I said. “Number Thirty, Mistress. OWW! Please let me serve you?” Pamela walked around to the front of me.
Grabbing my hair and lifting my head she said. “So are you ready to serve me Todd in all ways?”
“Yes Mistress. Please let me show you how ready I am? I will serve you with all my heart.” I responded.
Thrusting the Paddle against my lips Pamela said. “Kiss the paddle and beg me to use it on you whenever you are not pleasing.”
“Mistress, beat your slave with this paddle whenever he does not please you.” I said and I kissed the paddle opening my mouth I even tongued it to demonstrate to my Mistress that I meant every word. “Thank you Mistress for beating your slave. Please let me serve you.”
“We shall see Todd how well you can serve.” And laying the paddle on the floor Pamela untied me.
Once free I fell to my knees and kissing her feet I begged. “Please Mistress I am ready to serve you.”
“Place the paddle on the stool and then crawl to the bathroom and run me a bubble bath. I wish you to oil and massage my body and then wash me, Todd.” Pamela instructed.
I put the paddle on the stool where it would wait for me if I case I was not diligent in serving all of Pamela’s wishes. I then rushed into the bathroom and turned on the water to the tub. Checking with my hand the temperature I added bubble bath and bath oil to the water. Rolled next to the tub I found plastic coated cushion that I spread on the floor next to the tub anticipating that this would be where my Mistress would want to lay while I massaged her. I spread a couple of soft towels over the cushion so the rough plastic would not offend her body,
I heard a noise behind me as my Mistress entered the bathroom. Turning my forehead touching the floor I said. “Mistress I am ready to serve.”
I looked up to see Pamela standing in the doorway nude. She took my breath away. I had seen her naked many times but never before in these circumstances. I was kneeling at her feet and my desires meant nothing to her. All that mattered was her desire and needs. Pamela is about five feet three inches tall. She has strawberry blonde, almost red hair and her pubic bush is a deeper rust color. She is full figured sort of like a Marylyn Monroe look. Full hips and large beautiful breasts with pink nipples. She has freckles that trail down her cheeks onto her shoulders and stopping just above her tits.
“I see you are resourceful Todd.” Pamela said as she lay down on the cushion on her belly. “Use the flavor massage oil of your choice boy, after all I will definitely want you to be using your tongue at times during this massage.”
Not quite understanding her meaning I looked around and then saw on a small shelf a collection of flavored massage oils. I choose the plum flavored for no particular reason other than the looks of the bottle. I also grabbed another towel folding it and placed it for Pamela to rest her chin on while I massaged her. I shut off the water to the tub and prepared to start the massage.
“Start with my shoulders and back then move to my feet, I want my ass last to be massaged.” She ordered as she pulled her hair off her shoulder.
“Yes Mistress.” After rubbing my hands together to warm them I squeezed a liberal amount of the massage oil on her shoulders and started massaging it in.
“You may kiss and nibble my neck and ears while you massage me boy. Be inventive and make me happy.” Pamela ordered.
I leaned forward and started kissing her neck, the smell of plum strong from the oil. I rubbed deeply the oil into her shoulders. As I worked down to rubbing the small of her back I kissed and nibbled at her shoulder blades. I caressed and rubbed her back for about five minutes kissing and moving lower I skipped her ass with my hands but not my mouth. I kissed each of her butt cheeks then flicked my tongue starting at the top of her crack sliding my tongue down. I just tenderly kissed and licked along the outside of her crack until I nibbled where her ass cheeks met her upper legs and I was satisfied when she a sighed with pleasure.
“You are doing well slave.” She whispered.
I stopped kissing her ass and knelt at end of the cushion. I lifted one foot and ran my lips and tongue over her arch then pouring some oil in my hands I started massaging her foot, then calf and finally her thigh. When I finished that leg I lifted the other foot doing the same with mouth to her arch and then pouring some more oil on my hands I massaged this leg. Her legs were spread and I had a wonderful view of her slit and the view increased a desire for her that had my cock straining against the light silk underwear.
Having finished her legs I poured oil on each ass cheek and I started rubbing it in. My hands spread her cheeks and my greasy fingers played up and down her crack stopping and massaging her nether hole. Pamela was breathing heavy and the smell of her sexual arousal started filing the room. I leaned close to her asshole and puckering my lips blew at it.
“Oh Todd, My wonderful slave.” Pamela said and then she rolled over.
I started at her feet this time and moved up her legs. I spread her legs kneeling between them as I massaged her inner thighs. Skipping her pussy I kissed her lower belly just above the hairline of her bush. My lips and tongue moved up her body as my hands slide up her sides massaging. By the time I was sucking on the hard nipples of her tits my rock hard dick threatened to tear through the front of the red underwear.
Feeling my dick rub against her pussy lips Pamela said. “Just keep that thing in your pants. I have no interest in it now. But you may use your mouth where your dick is rubbing.” And pushing at my head she added. “Lick my pussy boy.”
I moved back down her body kissing and licking my way to her sex. Using my hands I spread her slit and began sucking on her clitoris. As I did this one of my hands lifted underneath her body rubbing her asshole and the other hand dipping two fingers into her pussy.
“Oh Todd don’t stop, that feels so good.” Pamela murmured lifting her hips and using her hands at the back of my head she pushed my face harder into her pussy. I kept up using my tongue to lick and my lips to suck on her love button. After about five minutes of this manipulation Pamela with a loud sigh moaned. “Oh Todd I’m coming don’t stop.”
Then with a shudder Pamela came. The muscle of her legs and stomach tightened with orgasm. As she subsided she grabbed my hair and jerked my head away from her pussy and said. “That’s enough Todd, Just finish preparing my bath and let me rest for a minute.”
Smiling I moved around my Mistress turning on the hot water to warm the bath water. I grabbed a towel to wipe my face from the juices of Pamela’s orgasm and my hand trailed down inside the red satin underwear and idly started stroking my raging hard dick.
“Todd what are you doing?” Pamela said slapping at the hand inside my underwear. “Did I give you permission to pleasure yourself?”
Pulling my hand out of my underwear a
nd feeling guilty I said. “No Mistress, I’m sorry.”
“Take off your clothing boy, I have a solution for your problem. Later a
fter my bath I will punish you for your audacity,” Pamela said.
I untied the vest, took it off and then slid the underwear down easing it past my hard cock and then off. Pamela was at the sink with a washcloth running water and soaking the cloth. Turning to face me she said. “Boy put your hands behind your head and spread your legs.”
Not sure what to expect I spread my legs a little wider than shoulder width and crossed my hands behind my head. Pamela took the washcloth and put it on my balls and dick. The washcloth was ice cold, she had soaked it in cold water. I gasped for air and tried to step away from the cold cloth.
“Stay put boy or I’ll have you get me ice for this. I’ll freeze your balls and then I’ll warm your ass.” Pamela ordered.
I stood still and felt my balls and cock shrivel as the cold shock of the washcloth drove all desire for sex from my mind. Again Pamela taught me that I was the slave and my job was to please her and not myself. It took a tremendous amount of will power to stay still as Pamela dipped the washrag again under the faucet and I shivered again as the cold, wet rag was wrapped around my dick and balls.
“After you finish bathing me boy.” Pamela said “I want you to remind me to punish you for playing with yourself without permission. Do you understand Todd?”
“Yes, Mistress.” I said. “I’m sorry for my actions.”
“That’s okay.” Pamela said throwing the washrag into the sink. “Now help me into the tub.”
I carefully placed my hands around Pamela’s waist and helped her into the tub. Pamela sighed as the warm bubble bath enveloped her body.
I knelt next to the tub and as I soaped up a washrag to wash my mistress’s luscious body she said. “Gently boy.”
I washed my mistress from head to foot gently massaging her body with the soapy rag. Pamela relaxed and seemed to enjoy my ministrations immensely. After fifteen minutes of soapy massage Pamela said. “Boy I want you to use the big towel to dry me.”
I quickly stood and holding the towel open I waited for my mistress to exit the tub. Pamela let me stand there and wait for a couple of minutes, relaxing in the warm water. When she stood I held out my arms and steadied her as she exited the tub. I then spread the towel around her body so the air would not chill her damp skin. Gently I dried her with the towel.
When dry Pamela said. “My robe boy.” I quickly grabbed the blue terry cloth robe hanging from the towel tack and held it for my mistress as she slipped into it. Leading the way into the bedroom she said. “Follow me boy.”
I followed Pamela into the bedroom and luckily remembered her orders knelt at her feet as she sat on chair near her dressing table I said. “Mistress you said to remind you that I am to be punished for playing with myself.”
“Ah Yes, good thing you remembered boy.” Pamela said. “It would have been far worse on you if hadn’t.” Turning to face the mirror above her dressing table She said handing me a hairbrush. Brush my hair while I consider how to punish a boy who thinks he can just play with his dick whenever he feels the least bit horny.”
Quickly I stood and taking the brush I began brushing with long strokes Pamela’s light red hair. “Yes mistress.” I worried about what she could be planning for me. At first I thought for sure it would be more swats with the leather paddle waiting for me on the stool, but now with her thinking about it I was unsure what I was in for. So far Pamela had surprised me at every turn and my feeling of servitude and dependence on her; my having to bend to her will just kept increasing.
Snapping her finger Pamela said. “I know, boy fetch the duffle bag.” I quickly fetched the bag and handed it to her. “Put your arms behind your head and spread your legs.”
Remembering the cold washrag when I received this command earlier I timidly obeyed. Pamela searched around in her duffle bag and came out with a weird contraption. It was sort of sleeve with a small sack under it and cords for tying. It was made of the same red silk as my slave outfit.
Pamela started rubbing my cock and getting it hard. “We’ll see how you do with this thing of yours all tied up.” I realized then that I was in trouble. When my dick was semi-hard she slid the sleeve over my cock, pulling it down tightly around my swelling cock. Then she wrapped the sack around my balls and taking the silk cords she tugged it around my scrotum. “Now let’s see how comfortable you feel about a hard cock tied up in this.”
She pulled the cord so that my dick and balls were tightly wrapped in silk. She didn’t tie the thing to the point of me being in pain but it was really uncomfortable and I knew there was no way I had enough room in there for me to get a full hard on. “Please Mistress take it off.” I begged. I also knew that I was going to have to move carefully or I would put a strain on the thing that I really didn’t want to experience.
“Just quit that begging, that dick and ball restraint will remain in place for as long as it pleases me.” Pamela said. “Now I want you to get up on the bed on your hands and knees. I have a little surprise for your asshole also.”
For my asshole, I really didn’t like the sound of that. I hesitated for a moment and said. “Please mistress, I won’t play with myself again with out permission.”
Pamela ordered. “Either to the bed right now or bend over the stool. I’ll warm up that ass with the paddle then have the fun with your asshole.”
I decided that I didn’t want a spanked ass to go along with what ever else Pamela had planned so I quickly crawled unto the bed and said. “Please don’t spank your slave again mistress. I’ll do whatever you order me to.”
“Okay, Todd. But one more time you don’t immediately obey me, You’ll go over the stool, I’ll tie you down, Spank you till your bottom is red as a cherry and then I’ll do to your ass what I have in mind.” Pamela said to me sternly. “Now put your head and shoulders down on the mattress. Stick your ass up high. That’s it.”
I obeyed each order exactly as she commanded. “Spread your knees a little. Now reach back and pull your ass cheeks apart so I can see your little brown hole.”
I stretched my hands to the cheeks of my ass, which was still a little sore from the earlier punishment and pulled them apart. “Yes Mistress.” I said as I felt the cool air touch the tender area of my asshole.
Pamela sat down on the bed next to me reached in her magic bag and pulled out a tube and showed it to me. The label read something like ‘Sex Lubricant’. ‘Shit’ I said to myself silently. I had a strong feeling what was coming out of the bag next.
Pamela said. “Ahh! Here we go.” And pulled a six or seven inch dildo out of the bag. “You were thinking about putting that dick of yours into me and fucking me.” Pamela said laughing. “Now I think you need to see how it feels to have a big dick stuck inside of you slave boy.”
Pamela pushed the dildo towards my face and said. “First suck my toy dick.” And as I opened my mouth she pushed it in. “Suck it good.”
I sucked and licked on the dildo, my cock and balls restrained and my ass cheeks spread waiting for the invasion of my asshole with the dildo that I was sucking on.
Pamela took the lid off the lubricant and pulling the dildo out of mouth said. “Now beg me to fuck you slave.” She started smearing the dildo with lubricant.
As the dildo started to glisten in the soft lights of the bedroom I begged. “Mistress please Fuck my Asshole. Please Mistress Fuck me good.”
Again laughing Pamela moved behind me. “Pull it apart farther boy.” And as pulled my ass cheeks farther apart I felt the head of the dildo rub against the tight entrance of my asshole.
As the dildo head started to enter and stretch the tight skin I begged. “Please Mistress slowly.” We had played with small butt plugs during sex before but none of u
s had ever been invaded with something like this before.
Pamela knew that my asshole, like hers was relatively virgin territory s
o she slowly eased the dildo in. The sensation was really different; she was pushing it in so slowly that it was only on the edge of pain. It didn’t quite hurt and when she said. “There we go it’s all the way in.” I couldn’t quit believe I had taken it all the way. “How’s my little slave doing?” Pamela asked.
Pamela had come out of role a little just to make sure I was handling the new experience. “I am okay mistress.” I said. This let her know that we had no problems and she slowly started sliding the dildo in and out of my ass.
She fucked me for about five minutes and then leaving the dildo stuffed in my nether hole, she removed her robe and slid her body around so that my face was again above her cunt she said. “Eat me slave.”
As I licked my Mistress to another orgasm I had to every once in a while reach back and push the dildo back in my hole. It kept trying to slip out.
Finally Pamela came again with a loud moan. “Oh that is so good slave boy.”
When Pamela caught her breath she ordered. “Go into the bathroom and wash the dildo and return quickly.” But as started to pull it out she commanded. “Just leave up your ass till you get in the restroom.”
It sure was embarrassing getting off the bed, balls and cock still bound, holding a seven-inch dildo up my ass and walking across the bedroom was humiliating experience. Pamela laughed. “Be careful boy.”
I entered the bathroom, her laughter ringing in my ears, I pulled out the dildo. Turning on the water I soaped the thing and washed it clean.
When I return to the bedroom Pamela was sitting on the edge of the bed with a dog leash in her hand. On the floor at the foot of the bed she had spread a couple of blankets and a small pillow.
“Come here boy and kneel.” Pamela ordered.
As I knelt at her feet she attached the leash to the collar around my neck and then tied it to the bedpost at the end of the bed.
“Lay down on your back.” She said indicating the blankets at the foot of the bed. She reached down and untied the restraining cloth from around my cock and balls.
The relief of no restraint was tremendous and I instantly started getting a raging hard on. “You may now Jack off.” Pamela said. When you cum catch it with your free hand, I don’t want squirting all over the place.”
Pamela layed on her side and watched her slave masturbate. It wasn’t long before I came and squirted a huge load of cum into my left hand.
“Mistress, may I go to the bathroom to wash my hands.” I asked expecting her to unhook my leash.
“No boy you may not. Just lick it clean and go to sleep.” I was shocked, but seeing the look on my mistresses face I started licking the cum off my and hand, swallowing it. I thought after all there had been many times that Pamela had sucked me to an orgasm and swallowed my cum!
When I finished licking my hand Pamela said. “Good boy now go to sleep.”
As Pamela slid up under the blankets on her comfortable bed and shut off the lights, I her slave wrapped myself in the thin blankets and tried to get comfortable on the hard floor. I, a slave would sleep on the floor. It took a while to doze off as I wondered what else Pamela had planned for her slave the rest of this weekend.