tom's fucking

As you'll recall from a previous blog entry, tom's sex shop humiliation, I gave tom and his wife a suggestion for some nice humiliation for tom to start the New Year off well. The first part was to go to a sex shop and buy a big strap-on dildo and a schoolgirl skirt for tom to wear while his wife takes him. Here is the second half of poor tom's tale...

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It was an evening that started out not that much differently from many others. J and I had a lovely dinner and afterwards I spent a blissful hour massaging her feet, after (of course) kneeling before her on the couch, begging her for the pleasure and lavishing her feet with kisses. J was smiling, contented and relaxed. Her smile then got that evil little twist in it, and she stared right into my eyes and pointed to the floor beside her. This is her signal that I am to kneel before her with my head lowered, and I quickly obeyed, my cock starting to grow as I felt her control wash over me.

J stroked my hair and lifted my chin, staring right into my eyes at close range. "Now slave...isn't there something we've been meaning to do?"

She smiled as she saw me start to tremble. "Yes, my Lady," I whispered.

"Oh slave...are you shaking?" J asked tauntingly. "Well...I'll be giving you something to shake about soon! Now...pour me a glass of wine and then go and prepare yourself exactly as Julie instructed. Understand?"

"Yes, my Lady," I responded. I crawled to the kitchen and poured her a glass of Merlot, then brought it back and presented it on my knees. J smiled and said, "Go now. Though what do we say first?"

"Thank you my Lady. And thank you Miss Julie," I responded quickly. I crawled out of the room and headed upstairs to prepare myself.

I went to the bedroom, removed all of my clothes, slid on my collar and waited for J to come upstairs. She had decided not to observe or participate, but wanted to be close in case I needed any help from her. She arrived in our bedroom, slid one hand across my cheek as I knelt and whispered in my ear, "are you ready, slave?"

"Yes, my Lady," I whispered. J smiled and simply said "Go."

I went to the bathroom and lubed my slave hole, sliding a finger in and out and moaning softly as I fucked my ass. It felt sooooooo good, and like a small preparation of what was to come. I generously coated my ass and hole, trembling all the while at how like a complete slave it made me feel. I then took out the enema kit and stared at it, my heart racing.

I had never given myself one before and was really shaking as I filled the bottle and slid the hook in place. I took out a towel and stood on it as you had instructed and got everything ready. It felt like it took forever for me to get my nerve up, but then I felt my submissive nature take over as I slid the tube into my ass. It felt like forever again before I let the warm soapy water inside me, but once again I knew I belonged to J and was under her and your instructions and had no choice.

As the water entered me I was shocked at how loudly I gasped! It was unlike anything I have ever felt before, and I squirmed and moaned and danced...you would have laughed your head off watching me! :) I immediately had to put both hands on my ass to keep myself clamped shut, and then stared at the clock on the bathroom wall, willing myself not to fail. As the wretched second hand made its final circuit on the fifth minute I felt a twinge of subby pride that I had survived the first round. Only two to go...

Knowing what was coming made the next two both easier and more difficult. I definitely got each one going a lot more quickly, as I spent a lot less time standing there afraid of the unknown, but I felt more and more...owned I guess is the right word, knowing my wife was lying on our bed on the other side of the door and that I was preparing myself to be taken by her new, enormous strap-on. This was thrilling and humiliating, and while my mind was reeling and heart racing, my stiffening little cock told me I was where I belonged, where I truly yearned to be.

My slave hole was so sore after the third one! I had been clamping down so hard to keep all the water in as you had ordered (J had promised severe punishment for spilling), and my ass was sore in a way I've never really felt before. I've felt the sting and pain from a good belt whipping (especially after my typo disaster!) but never this kind of soreness. It was thrilling and made me feel incredibly submissive, but in the back of my mind I wondered how I was going to survive the rest of the night...

I took a long hot shower and cleaned my slave hole one more time thoroughly with soap and water. Along with being so sore I also felt really clean back there, which was kind of a good feeling. Especially as I knew I had cleaned myself for the pleasure of J. I then crawled out of the bathroom and laid a towel down on the floor next to the bed, where J was stretched out luxuriously, looking incredibly sexy in satin pajama pants and a tight t shirt. I spread out the towel and laid down on it, again as you had instructed. J smiled, browsing the internet and glancing down at my trembling form beneath her.

Turns out she had a surprise for me though...after about 30 minutes J ordered me to close my eyes and I heard her open our toy box. I felt out black leather blindfold slide over my eyes, and then felt her straddle me, her satin-clad thighs feeling like heaven as they closed around my legs.

"Are you all clean, slave?" she said mockingly. "And did we make sure not to spill anything?"

"Yes, my Lady," I whispered. I so longed to see her sitting on me...it is one of my favorite views in all the world, which is why J sometimes delights in denying it to me.

"Very good, dear," J said, the mocking tone still in her voice. "Now...we've got a big night planned...how much longer do you think you need on this towel before I can take you?"

"I...I'm not sure...maybe ten more minutes, my Lady?"

"I see...well...if that's what you feel you need, slave. But nothing comes for free, my love. So...." I suddenly felt the sharp sting of a wooden clothespin on my left nipple. Then another one on my right nipple. I gasped and writhed, but was trapped under J's thighs. She laughed and flicked each pin cruelly. Then I felt her slide another one along my naked, defenseless torso.

"Let's see...a clothespin for every minute is fair I think." I could almost see her wonderful wicked smile. "But your poor nipples seem taken now...oh dear, where shall we put the others?"

I whimpered and J immediately stuffed a small black ball gas in my mouth. "Now hold that in dear," she said firmly. "I won't have any whimpering. You decided you needed ten more minutes, I'm only trying to pass the time and amuse myself before the real fun starts!"

She clapped her hands and giggled, and I felt myself turn to jelly underneath her. I held the gag fast and tried my best to keep silent and she secured a clothespin on each of my upper arms. Then she slid one slooooooowly down my chest and clipped it to my stomach, laughing as she flicked it with delight.

Five down, five to go...I felt J slide down my legs and trembled as I knew what was coming. I moaned against the gag as she clipped my now throbbing cock once...then again. Then on on each ball.

 Then she turned around and placed one between the second and third toe on my left foot. Laughing as she said, "and one to grow on!" she clipped my toes on the other foot as well.

I felt her climb off of my and wriggled and writhed. My ass was so sore and now my tender flesh was screaming as the cruel clothespins did their work. I felt J standing over me, sliding her foot across my body, over my face, along my cock...flicking and pushing the wicked clothespins with obvious glee. I writhed and moaned against the gag, willing the time to move forward.

"Time's up, slave!" J slowly and wickedly removed the clothespins, flicking each one as she unclipped it. She left my cock for last and then removed the gag and blindfold. She pointed to the floor and I assumed my kneeling position.

"There...just wanted to keep you guessing, slave," J said evilly. "I know you know a lot of what's coming, but I don't want you for a second to think you know everything."

"Yes, my Lady," I whispered. My whole body was shaking as I felt her hands on my face. She kissed my deeply, passionately and said, "go and get dressed now, dear."

I stood and opened the dresser drawer where the skirt we had bought was folded neatly. I took it out and slid it up my legs, my cheeks burning red as I heard J laugh softly.

"Ahhhh...that brings me back. Remember Stef my dear? Once we're done tonight perhaps we'll make a return visit to that store and fill her in on our evening...what do you think?"

As I heard Stef's name my mind turned back to the sex store and my utter public humiliation. The thought of returning to give Stef the details made my cheeks burn red hot, but also made my cock throb like the slave I am. I answered "whatever you desire, my Lady," in a quavering voice, and J laughed even harder.

"Give me a twirl, dear." I obeyed, twirling and making the skirt flip up, my hands above my head. I was so utterly J's plaything now.

"Very nice. Now come over here." I approached and J grabbed me roughly by the hair and pulled me over her knee. "Who do you belong to?" she asked.

"You, my Lady. I am yours."

J lifted my skirt up and CRACK! Down came the wooden hairbrush on my tender ass. Since we had been apart for a while I had obviously not been spanked all that much recently, and my tender flesh immediately burned. I yelped and squirmed but J held me fast, wrapping a leg around mine and holding my neck down firmly.

CRACK! CRACK! CRACK! CRACK! CRACK! CRACK! CRACK! CRACK! CRACK! CRACK!

J delivered ten HARD blows in quick succession and I was screaming by the last one. She cooed and slid her hand across my now burning cheeks, caressing the red marks I could already feel forming. "Ah that Julie," J said..."She does know her stuff. I will enjoy this so much more with your ass nice and red!"

J mercilessly spanked me with the hairbrush, varying between hard and soft smacks, moving from my cheeks to upper thighs and back again. Her hand sometimes caressing my now burning flesh, inspecting her handiwork before she returned to her work. I lost count of how many spanks there were as my mind dropped deep into a submissive space, my whole body shaking and pinned down my J's hand and leg, my will completely subjugated.

Finally, mercifully, I felt J's hand again...and then I felt her leg slide off of mine and her hand release. I slid down to the floor, shaking and knelt once again. When J permitted me to look up I saw she was holding our old butt plug and some lube.

"Stand, slave," she ordered. I stood and she led me to the corner of the bedroom. "Now...I want this inside of you, and then I want you to press your nose into the corner and hold your skirt up so I can enjoy the view."

She handed me the lube and plug and returned to the bed. I lubed up my slave hole again, sliding a finger in and out. Then I took the plug, the only one I had ever known, and began teasing my hole with the tip. The enemas had left my anus already incredibly sore, and I felt it stretch against the plug, making the soreness even worse. J laughed as she saw my knees buckling while I fucked myself for her, sliding the plug a little deeper. It has two widths on it and she laughed again as I moaned and pushed the wider part inside my slave hole, pressing it as deep as it would go. I then pressed my nose into the corner and lifted my skirt, all while J laughed and applauded.

"Very good, slave! Such a little slut for Mistress!"

I stood there, grinding my nose into the corner as J approached. She slid her hands down my back, my whole body an exposed nerve to her simple touch. She then playfully spanked my screaming ass a few times, delighting at how I jumped at each SMACK of her hand. Then she took the base of the plug and began sliding it in...and out...in...and out....my knees buckled, hips rocked and soft moan escaped my lips as J teased my sore anus.

"Who do you belong to?" J whispered in my ear. She began fucking my slave hole faster and faster.

I could barely speak. "Y...You, my Lady."

"Yes....you are my little slut, aren't you?"

"Y...yes, my Lady." My cheeks reddened as I agreed.

"Good." J then abruptly removed the plug, grabbed me by the ear and brought me to a kneeling position. I crawled behind her to the bed, where her strap-on was waiting.

It looked HUGE. I felt my ass clench involuntarily as I gazed at it, knowing J was going to take me with it...use me...wring me out to dry with that huge cock. She didn't say a word, simply handed me the strap-on and stood before me.

I slowly slid the strap-on up her beautiful legs, shaking as I brought it up over her lovely hips. I was shaking so much that I struggled with all the little doodads for tightening everything (J even had to slap me once and tell me to focus) but eventually I got it secured and comfortable and to J's liking.

I knelt there, in a position I have never been in before. J loomed over me, her cock enormous as it hung there before my face.

"Kiss it, slave," she commanded, all amusement out of her voice now. I have always been amazed and completely enthralled when she becomes fully commanding, and she was definitely in command now.

I placed a kiss on the head of the cock. J took it and slapped my face with it. "Again," she ordered. I kissed it again, and J smacked me with it again.

"Now...you know what you are going to do now, right? Julie's instructions were clear, and I expect a good performance."

"Y..yes, my Lady."

I took her cock in my hand and opened my mouth. J stopped me.

"Not yet...beg me," she said, her voice icy and stare even icier.

"P...please...my Lady. Please may I suck your cock?"

J slapped me again with the cock. "You can do better slave...BEG."

"Please my Lady! Please let your slave worship your cock!" I practically yelled.

"Better. You may begin."

I took the cock and slid my lips over the head. I had never done anything remotely like this, and was tentative at first. J quickly grabbed a handful of hair and stuffed her cock into my mouth. I gagged and tried to move back, but J was firm. She took my mouth, sliding the cock deep inside and then removing it to allow me to thank her and beg again. The begging added to the humiliation, but I found also made me more eager. After a short while I was sucking her cock with vigor, my submissive side fully engaged and her smile all the pleasure I required.

J then grabbed my hair again and began fucking my mouth with gusto. I gagged a few times and she always pulled back, but never let me take it out of my mouth. She moaned softly as she used me, gagging me again and again, pulling my hair, faster and faster, taking me completely.

She finally allowed me to remove my lips...as the drool dribbled off my lips I knelt before her in awe, taken, used, HERS. She had a glint in her eye and stared at me with such intensity that it made me tremble even harder. Without a word she grabbed my head and pushed me down, raising my ass into the air. She spanked my cheeks a few times, her passion roaring out of her and into each SMACK. I yelped and moaned and wriggled, but there was no escape.

J pushed me down, nose to the floor and slid behind me. I felt the tip of the cock press against my ass cheeks and felt terrified, thrilled, helpless, taken, and overjoyed to be J's slave. J slowly slid the tip inside, my sore, wrung out anus squealed in protest as I felt it strettttttttch me open. "I'm going to have you now, slave," J said, a hard edge to her voice that made my cock even harder and whole body succumb.

She slowly slid the dildo farther in...I felt like I was going to split in two but my sore slave hole was up to the challenge. J was slow and careful, opening me to her gently at first...but I knew what was to come. As the dildo went deeper and deeper I heard J moan softly, clearly enjoying herself. She teased and slid the dildo in with skill (especially since this was a first for her!), gently but firmly stretching me wider than I thought possible.

As the dildo got deeper she began slowly taking my slave hole. In....out...in...out...never coming all the way out, just using it to open me up. Then faster...and firmer...I moaned and screamed and writhed and whimpered and it just spurred her on. I was fully being taken now, J's hips thrusting against me as she fucked my hole, her moans showing how much she was enjoying herself and watching me struggle.

Faster and faster...deeper...harder...I screamed for it, begged for it, needed it. J responded, moaning and gasping herself as she took me. Then she slid deep inside and paused. I then heard the unmistakable sound of her small vibe...with her slave fully stretched and plugged she began sliding her vibe to her pussy through the straps...moaning and throwing her head back, pausing to push her cock deeply inside me and watch me struggle while she pleasured herself.

I heard her screams as she came, felt her fingernails scratch my back as she bucked, her cock sliding in and out. After she paused to recover herself she then said "Now I'm going to really take you...beg for it, slave!"

My whole body was sore and shaking, heart racing as I yelled "Take me my Lady!"

It's hard to describe the rest...I was wrung out (as you had wished I believe...), sore, on fire, shaking, blissful and completely her slave at that moment. J took me vigorously, sliding in and out, deeper and harder. I was amazed later thinking back as to how much I could take.

J then eventually slowed down, keeping her cock inside me however. "Does slave wish to cum tonight?"

"OH GOD YES," I practically screamed.

"Wellllll...you have been a good little slave, and I have thoroughly enjoyed myself. So you may cum...while I fuck you."

I practically exploded just at the words. J began sliding her cock in and out again...she permitted me to begin stroking my throbbing cock and my hips bucked and rocked against her cock violently as I stroked myself.

"May I cum, my Lady?"

J waited cruelly, fucking me harder...knowing I was dying for permission. She finally laughed and said "YES slave...cum for me..."

I exploded all over the towel and J cooed "gooooooood boy," as she watched me buck and heard my screams. I almost collapsed then but stayed in position, just barely. J slowed down and the sloooooooowly slid her cock out of my slave hole. She had me turn and kiss each foot.

"What do you say?"

"Thank you my Lady! And thank you Miss Julie!"

"Very good," she stroked my cheek tenderly, her eyes shining and smile wide.

J then had me slide the strap-on off of her and clean everything up. I returned and crawled into bed with her, utterly wrung out and exhausted. My ass was sore for days afterwards, a constant and wonderful reminder of an incredible night. J has promised we will be doing more of that.