It all started in the summer of 1998, back in Cairns, Australia. Marriage is a fickle thing, and mine had fallen apart over perceived jealousy and the fact that she just wasn’t meant for me, or maybe I wasn’t meant for her. It didn’t really matter any more, she gathered her things on a Saturday morning, called her parents, they came to pick her up, and that was it. I never saw her again, and the only conversations I had were short and angry with her wanting nothing more to do with me.
Life sucked at the time. I had a good job, was earning decent coin, and kept doing it, because I had to do something. But, I was empty inside. I’d loved the girl, and she had taken my heart and ripped it out of my chest, stomped on it, then kicked it to the curb.
I needed balance, I needed something. I had a second tragedy within a month of the first. My best friend in town, a young man by the name of Jay, who had been suffering for a while from mental illness, decided that on his 18th birthday we’d spend the night drinking at my place. I enjoyed a nip of whiskey, and he liked coolers. His parents agreed, so I got a couple of quad packs for him and we spent the night watching movies, drinking, and enjoying company. His mind dissolved over the course of that night as bi-polar disorder flared it’s ugly real head. As I held him in my arms, I saw the young man I had known for almost 8 years disappear, to be replaced by a paranoid, delusional creature who thought he was some Biker Gang god who could do and be anything.
Jay died by his own hand eight years later, unable to handle the Bi-Polar issues.
I was alone, feeling more alone than before, I sought out Jay’s father, who was a Tai Chi Master, and we spent a few solid weeks with me doing some deep in depth training with him to find my inner balance and focus my turmoil. He was willing to give me as much time as possible, and at no cost to me, because of what I had done for his son, but that wasn’t fair to him, so I took what I needed from the training, and then allowed him to go back to earning his income from his school.
Tai Chi balance, an interesting thing. I still retain it. It taught me to look at the entire world as a series of circles and spheres. I was quick study, learning hand and leg movements, body position and posture, and how to relax and pretty must just let things flow around me, not stand in the path like most people, and then deal with getting slammed.
My loneliness was still intense, and I tried the club scene, but the two girls I hooked up with were only interested in a quick fuck, nothing long term. So neither relationship was even that satisfying.
Next step, the internet. I did my day job, now able to save money as I had no reason to spend it any more, and began hunting the internet for my interests. I had always had an enjoyment with spanking and sexual dominance, but not violent dominance, the mind fuck was much more interesting to me. The ability to dominate with words and concepts rather than brute strength.
I found some chat rooms that were kind of kinky, but they focused on Gorean lifestyle, which was odd and bizarre, the way those people had torn apart John Norman’s world and rebuilt it into a real life multifaceted sexual thing. Not my scene. Then I came across what would become my home online for the next two years, a spanking chat site.
A web site that sold spanking pictures, videos, and audio tapes, like many others, but this one also had a chat server attached to it for communities. I played with the java server, then loaded up a copy of MiRC and dove heard first into a conceptual fantasy world that engrossed and fulfilled my need for my own control.
Being in Australia, and not being interested in just a toss during the chat made me different from the hundreds of men who would log on daily. I talked, listened, healed myself, and helped others to heal and understand their own needs. I refrained from sexual things during the play, even during the fantasy spankings, I only focused on the spanking aspects, not ‘pulling out my cock and sliding it in’ type of thing that most of the online guys wanted to do.
I was better than that, I was TheOldDragon, a sage who knew a lot about everything, was very experienced with spanking all types of naughty women, and who was not wanting to grab an online sub and lock her up – I was free, so were they. Time online was time to be treasured and enjoyed with the group, not locked in a Private Chat for a toss session.
It did not take long before I was getting real life propositions. Those intrigued me more than anything else, girls were willing to take this fantasy into reality, and try and make it work?
I hooked up with an online by the name of Baybe, and after a few months, she decided to take the plunge from her dead-end life in Tacoma and flew to Cairns to be with me.
Waiting for her at the airport was an intense experience. Seeing her come off the place, blonde, a bit older than me, curvy all over, wearing the typical LBD that hugged her and revealing everything while still being decent. We got back to my place and within ten minutes she was stripped naked, had a properly red bottom, and my hard cock was buried to the hilt in a hot wet pussy that really wanted my cum.
Our relationship was fast, it was a rebound for me, but I needed it because it gave me a purpose again. I ended my job and travelled back with her to the US, setting up shop with a company in Redmond making signage, which is my trade. I was working under the table being not a citizen, and this was part of the plan.
Within a month she was openly cheating on me, and encouraging me to cheat on her. This was not a monogamous laureateship, she was an active swinger. I wasn’t really a swinger, but did play a little. The couple we had stayed with were also very much into spanking, and I had an opportunity to discipline and then use the other woman for my own needs. I spanked her, but it never felt right so I never did anything else, even as Baybe was being fucked by Spice’s husband in the other room.
Then we did a mock wedding, and that was when things really heated up. For the wedding, we invited people from the chat room to come out and enjoy the time with us. We ended up with a group of about 10 chatters who came down for the wedding of TheOldDragon and Baybe.
That was memorable. I met people who for a long time I had known virtually, and now it was reality. Some of the girls were afraid because they were IRL virgins, but really had an interest. I was able to explore that interest with one girl, who’s online nick was BadGirl.
Ahh BadGirl, my darling lass. You were so nervous when we met. Hiding behind Trevor from Scotland who gave me a wonderful split tawse just built for naughty girls’ bared bottoms. So very nervous, you knew you wanted the attention, but were so afraid to actually ask. It took some doing, but eventually, I stepped towards you, Trevor sidestepped, and you were face to face with what had been fantasy before.
I held out my hand, and you very nervously put yours in mine, then I gently, oh so gently, guided you away from the group that you were hidden behind. As they all slipped away, Willow whispering ‘Good Luck’ in your blushing ear, and before I think you realized it, we were alone, me sitting on a bed, and you standing in front of me, biting your lip so hard you did draw blood.
I gently pulled you towards me, so that we were lightly touching, my knees to your thighs, and I could feel you trembling. You were so nervous, this had been a fantasy for so very long, you were truly a spanking virgin, always wondered, but had never experienced it. I am so proud that you allowed me to initiate you into this D/S world so that you could then go back to Minneapolis and explore it there with your future boyfriends and partners.
You pulled away as I gently pulled you towards a sitting position on my lap and you did step back, not hearing a protest from me as you walked to the doorway, then you paused and looked back. I looked at you, and then held both my arms up, and you came back, into a warm hug that helped to begin to put you at ease.
My hands holding you as you sat on my lap, trembling with nervousness and some excitement. Not too sure what to do next but willing to let me guide you and lead you down the pathway to fulfilment. I slid one hand up to caress your face as you looked not quite at me, not wanting to meet my eyes, acting the sub, because you were still so very unsure. Like a doe in the sights, not sure if you would bolt or stay still.
I pulled you down and gently kissed you, which surprised you, because you did not expect romance out of me, your lips opened slightly and you returned the kiss with a touch of boldness, still not wanting to meet my eyes, so you kept yours closed.
I pulled your head gently down so that you were nestled against my shoulder, and I felt your warm breath down my back, then I whispered into your ear ‘You don’t have to do this, but I do think you want to, don’t you?”
I felt you nod, tentatively, then with more certainty.
I pushed you back slightly and made you look at me. “I need to hear you say it, BadGirl. I need to hear the words.”
You mouthed silently, then a single word ‘Yes.” escaped your lips and you buried your head in my shoulder again, letting your light brown hair cascade down to cover your face as I felt you sigh with anticipation and nervousness.
I nodded, and Willow pulled the door shut, closing us off from the rest of the party. She had been watching from around the corner as I calmed you down, I think you knew, and even if you didn’t at the time, she told you afterwards. You had always been safe, and nothing bad would happen to you in my hands. You slightly jumped as you heard the door click closed, but stayed wrapped in my arms, slowly breathing as I could feel your heart pounding as you pressed your breasts against my chest.
I gently pushed you back to a standing position, and then I also rose, letting my hands rest on your hips as I looked into your green eyes.
“If you want to stop, if this gets to be too much for you, just say my handle, and I will immediately stop. Do you understand?” You nodded, and just to be sure, I asked you to say it to me. You whispered ‘Tod.” and then I again kissed you to help reduce your turmoil even more.
We were much closer in age than Baybe and I were, your 27 to my 31. In another life, we might have become a couple, or even something more permanent. For now, this was to be a one time event, and that is where it was best left, as one glorious time that left only memories of kindness, exploration, and pleasurable pain.
My hands slid around to cup your ample bottom, as you were comfortably curvy, the way I liked my spanking girls, and you knew it well. I gave a gentle squeeze, and you jumped nearly out of your skin as another jab of reality struck home. Then, one hand slid around to the clasp of your jeans and I gently undid it. You looked at me with a question in your eyes, and I smiled at you as I slowly pulled the zipper down.
“Bare bottom, BadGirl, just like it always should be.” You smiled, a crooked and weak smile as you allowed for the jeans to open, exposing a pair of pink panties to my sight. I slid my hands into the sides of the jeans and slid them down to your knees, then sitting down, drew you face down across my lap before you could even take a good breath.
I just let you lie there, supported on the bed, legs wrapped in your jeans, bottom covered by a small pair of high cut pink bikini panties, your teal shirt slowly riding up a bit as one of my hands continued to gently rub your back, my other hand caressed your bottom as your breathing quickened, then you took a solid breath and blew it out, and I felt your weight settle on my lap as you finally acknowledged what was about to happen.
My hands kept busy, one roaming across your bottom as the other continued to caress your back and as they gently caressed and rubbed you, you continued to relax, only to draw in breath sharply as my fingers slipped into the elastic and your panties were pulled down to bellow your bottom cheeks, I was unable to pull them further because of your weight, and for the now, that was OK. They would come off fully later.
I felt it was time, and my hand slowly slid off your bare bottom, leaving it cold, you drew in a breath as my hand smartly cracked down, once on each bared buttock. You jumped and gasped. They were not hard smacks, but they were firm, as I was. You could clearly feel my hardness beneath your hip as my hand continued to warm your bottom, slapping your cheeks firmly and beginning to bring some colour to them.
As I spanked, you began to wriggle and writhe a bit, gasping at the sensations, and the panties managed to slide down to tangle around your jeans which had now managed to slide to your ankles. I paused and stood you up, your face red, breathing hard, and tapped your knee. You obediently lifted it and I unwrapped your jeans and panties from one, then the other foot, leaving you naked from the waist down, eyes moist but not tears, yet. Those would come soon, as you wanted them to. You were neatly trimmed, as you did not feel the need to actually shave, so a neat brown bush met my gaze as my eyes looked you over, then I crooked my finger and you came to stand right in front of me.
Both my hands rested on your hips, this time, my fingers pressed against warm buttocks as my thumbs held you in place. I leaned forward and planted a kiss on your stomach, which was plump, rounded, and stuck out from your shirt just a tiny bit. You smiled down at me, and I looked up at you.
“Are you wanting to continue, BadGirl?” I asked softly, my fingers gently pressing and kneading your warm bottom as I looked up at you. You nodded, and I pulled you closer, then you were over my lap again, but this time, I positioned you properly. Your legs were slightly apart, so that my hand could comfortably rest in between them, and you jumped as my other hand left the small of your back and gently cupped your breast, feeling it’s firmness through the thin t-shirt and bra you had worn.
“Breathe, my BadGirl, this is the part that girls don’t like, but they do grow to enjoy.” I said, then began to smack your bottom firmly, my hand stiff as iron as it began to slap firmly, raising colour and stinging in your bottom almost immediately. I squeezed your breasts as I spanked you firmly, and within a few firm slaps, you began to cry.
These were cathartic tears, you had not really done anything wrong, but what your body wanted, nay, demanded was this form of punishment, and then the reward that tended to follow. As my hand continued to bring a solid red blush to your nether cheeks with the occasional dip between to stroke your growing heat, your body shed some of the turmoil and pain as you let go and became a submissive girl, being spanked for no other reason than because you could be.
I steadily spanked with a basic rhythm, warming and colouring your bottom until I sensed you were nearing your limit, and then my pattern changed, beginning to spank closer to the cleft between your legs as my other hand began to gently knead the breast that it held contained. You began to wriggle your hips as the heat from your sore and hot bottom began to seep inwards, also bringing a sharp reality to what had only been fantasy before.
I began to caress your bottom, with only the occasional slap as I began to really focus on bringing you towards a conversion of the pain into pleasure. Within few moment, your legs were wide apart and my warm hand was between them, fingers massaging your lips and caressing the nub of flesh at the top as your nipple was stiffly promoting itself through your bra and shirt.
You gasped, then pushed yourself off my lap and knelt on the bed, almost panting, hair in disarray, face wet with tears and eyes glistening with arousal as your body processed the feelings and began to really feel the sexual burn from the spanking. You looked directly at me as you pulled your shirt up and off, then swiftly undid your bra and knelt, naked on the bed, in front of me.
As I was about to say something, your mouth found mine, and you pushed me down with a burst of aggressiveness as you had to see if all of the fantasy could become reality. Your hands fumbled then undid my belt and opened my slacks, pulling me free of the confines of the pants so that you could hold my stiffness in your hands like the prize you wanted it to be.
Breathless, you looked at me, then your head went down and you wrapped those lips around me, tongue already hard at work as you began to bob your head up and down, laving my shaft with your oral attentions.
You raised your head and licked around the head, then went down again, bobbing and laving all down my shaft. Then you were up again and sliding up my body, nipples and hair dragging across my chest until you were sitting on me, straddling my hips. I remained passive, this was your fantasy trip to reality, after all, you really were in charge. I caught your eye, and looked over at the table, where some condom packages sat, you looked, then ignored them and gripping the base of my shaft, pressed him home into your wet slot.
Now before everybody begins ragging on me about safe sex and protection and all that. You need to remember one thing, I was TOD, TheOldDragon, one of the most knowledgeable and respected people on the chat server, with good reason. I did not make mistakes. I gave advice freely, and my advice was without bias or judgement. I didn’t care if a snarky sub, bitchy Domme, or testy Top was asking me the questions, I replied to all of them the same way, with fact, not fiction.
BadGirl had spent plenty of time with me online, and had talked to most of the girls who I knew IRL in the Seattle area, so she really did know me. I also trusted her, like I trusted all the people I was with in this small community that we had developed. If she did not feel the need for a condom, then I knew that she was not going to let herself become pregnant, and that she was STD free. I was STD free, and I remain that way. I work carefully with my people, and with all of my relationships, even the flings, was either fully aware of the history, or condoms were used, without exception.
BadGirl was living her fantasy, and wanted it bareback, who am I to deny her that thrill.
31 years old, with a nearly orgasmic bbw 27 year old riding on my hard cock, my hands wrapped around her fleshy red buttocks, feeling the heat from them, feeling it as it seeped into her hot pussy and the slickness as she slammed up and down on me, driving herself towards a climax. I was self-taught in basic Tantra, so I was able to not only reduce my orgasm impulse, but stiffen myself and work my own muscles to caress her g-spot as she rode me.
As I expected, BadGirl came, all of a sudden, almost as a surprise to her. She stopped, gasping, then fell on me as I felt a flow of wetness from her nether lips wrapped round me and her sheath gripped me in convulsions as she pulsed.
I held her, allowing my stiffness to relax, but I was certainly not going to soften, and held her, rubbing her naked back and caressing the back of her head under her hair as her breathing slowed, then she came back to her senses and sat up on me.
“That was … amazing.” She breathed, and I chuckled. “Welcome to the world of spanking stimulation, BadGirl. I hope you are enjoying it.” She smiled, then wriggled her hips so my shaft moved a bit in her, and she began to bounce some more.
I felt it was time for a bit of dominance, so I rolled her onto her back, and took the missionary position, putting her arms up over her head so I was holding her wrists and with her legs now firmly wrapped around my waist, began to properly drive into her.
Now in a position where she had no choice but to enjoy, losing all control, she began to have small multiple O’s. Not earth-shattering, but body rippling, pussy slipping, breath gasping orgasms that kept her rolling until I felt the urge coming and this time pushed it through so that I surged into her, feeling myself swell, then spurting my seed into her as I pressed fully against her, feeling her still warm buttocks against my thighs and the dampness seep from between us.
I gently released her wrists and she tested them, making sure I had not hurt her, then I leaned back on my haunches and slid out of her, letting a bit of my semen spill out of her with a gasp from her at the loss of the full feeling she had.
I helped her to a sitting position and cuddled her as she chatted about what had happened. All her feelings and random thoughts coming out as she relaxed in the afterglow of her fantasy made real.
My darling BadGirl, you were a jewel. I thank you for the time you gave me and allowed me to share with you.
My next girl was also from the chat rooms, and was my almost soulmate until I met my angel. Boonie, or lil-boonie as she referred to herself.
An adorable young lass from the East US who is now a School Librarian. Never been touched, she was a 28 year old virgin when I began to chat with her, and she found a soul mate in me that she had never felt with anybody else. She had enjoyed spanking with a neighbour and some friends, but no proper sex, that was not permitted. Although she had permitted her friend to take her bottom so she could have that feeling known, and she had taught herself oral skills to please the man, but had never allowed penetration, until now.
My Boonie, we chatted on the phone, and talked over chat for months before she arranged to finally fly out to meet me. At Disneyland. I went down for a four day weekend to meet some of Baybe’s swinging family and see if there was any real chance of recovering the failing marriage. There wasn’t. In the time we were down there, she slept with three guys, including her cousin.
I met Boonie in a Denny’s at 11pm at night, because she flew in later than we did, and I was sitting there when she came in with her twin friends who had agreed to be her chaperones as her parents were very protective of their special little girl, even at her age, and she didn’t want them to think anything bad was going to happen; but she did plan, and her friends were fully aware of it, and in agreement that it was time.
She was exhausted, and nearly fell asleep as we sat there eating a late night snack, then I looked at her friends and said to them “I think Boonie can stay at my hotel, it’s just up here.”
The twins looked at each other, then at Boonie, who was sitting between them, anticipating and excited, but also very tired, and agreed. They got up, and she slid around to sit by me, cuddling into my arm as the two girls bade us good night with a promise to meet them at the Disneyland gates by noon tomorrow.
We sat for a few more minutes, then Boonie pressed against me and yawned heavily, she was really exhausted. A cross-country flight will do that to you. I quickly paid the tab, then helped her to her feet and picking up her small bag, walked with her back to the hotel and up to my room.
Boonie, you were so demure and innocent, you knew what you wanted, but were still nervous about what was going to happen and I wanted to be so very careful. You wanted me, and I knew that I wanted you as well, but you were virgin, I needed to be so very careful to make sure this first time was so special you would only know pleasure, no pain.
You earned and deserved that alone, for the time you gave me, and I am so pleased that I managed to give you the pleasure you wanted.
You blushed as I took charge and walked you over to the bed, then sat down and lifted the t-shirt off, exposing your breasts to my gaze, as you had no need of a bra, small, flat breasts with little cherry nipples and tiny pink aureola. I undid the belt and unclipped the button on your shorts, and with a helpful wriggle, they were down and off your feet quickly, leaving you in just a pair of white panties.
I left those on, and then looked at you. “I think we both need a shower, then we can sleep.”
You nodded, and allowed me to lead you into the en suite. I turned on the water and set it to quite warm, then swiftly undressed until I was just down to underwear as well. You were so adorable, eyes everywhere except on my erection, even though you kept sneaking glimpses at it.
I had you put your hands on my shoulders as I slipped your panties down, exposing you fully to my gaze as I looked upon your nakedness. As you knew what a sub should be, you were fully shaven, you had been doing that for months, I recalled. Liking the little girl feeling, the innate naughtiness, and also the submissive feelings that it gave you to remove your adult hair for a possible master.
I gently turned you around and had you step into the cubical so that the water cascaded down around your head and shoulders, your close-cropped black hair spatting into wetness, rivulets of water running down your compact body as you felt the warmth and heat from it. Then I was naked and in the shower with you. You still refused to look at my erect cock, even though you wanted to, but it was improper for a young southern lady to do such things, even as we were about to do something most improper.
I took some liquid body wash and gently lathered you up from neck to groin, having you turn slowly and washing your entire body down from the long flight, letting my fingers linger over your most sensitive parts, lightly rubbing and slippery pinching your nipples, then gently caressing your stomach and below, making your breath quicken.
You were too demure to wash me, which was OK, I quickly washed myself, but took your hand and placed it on my cock, and you held on, firmly, still looking st my chest rather than what your hand was holding, occasionally looking into my eyes with a furtive glance. I had us both get out of the shower and turned it off, then taking a couple of towels, thoroughly dried you, making sure every inch was dry from the water, then taking another towel, dried myself, and walked naked with you back into the main room where the bed was.
I walked you right over to the bed, then stopped you and sat down, pulling you against me, so that we remained, touching intimately, two naked adults, me sitting, you standing, feeling the light pressure of your breasts against my chest, you feeling my hardness pressing against your legs and crotch as it made it’s presence known. You looked at me, then I leaned forward and gave you a gentle kiss. You pressed into the kiss, nervously, unsure, never really having kissed anybody properly before.
I kissed you tenderly, nibbling your lips and then gently broke the kiss, one of my hands caressing your head and check, the other firmly planted on your trim backside, holding you against me.
“Are you ready, my girl?” I asked you tenderly. You shook your head with a small smile. “No, but I want to do this. I trust you.”
I kissed you again then pulled you down onto my lap, so my hardness now pressed against your thigh. One hand now resting on your hip, the other gently rubbing your breasts as you continued to explore kissing.
During a pause in the kissing, you found yourself being laid back down on the bed, with a towel under your hips, then I was lying beside you as the kissing continued. You were tense but excited. Wanting but wary.
My fingertips slipped down to your stomach,then went lower, brushing the top of your mons, then lightly rubbing your lips, which were slippery with anticipation. You put a hand down as a token defence, only to have it gently but firmly moved away as I continued to explore your most private places.
As my fingers kept up their busy work, gently caressing and sliding up and down your slit, getting you wet and more excited, my other hand firmly now held both wrists and my mouth was busy kissing your neck and behind your ear, which for you was an intensely erotic place.
You were already wet when we started, I bought you to a climax quickly, and you came, bucking against my hand, straining against my restraining grip as your body released it’s tension. I continued to rub your clit and caress you, bringing you through your orgasm and back down to the reality we had chosen together.
The nervousness came back when you felt me shifting your legs further apart and you knew what was going to happen next. I released your wrists and you watched as I took a tube of KY jelly, then put a copious amount on my hard cock, lubing it up as much as possible, then my wet fingers also stroked your slit and as you gasped, my fingers lubricated the opening into your body, rubbing KY all around your entrance and some just inside.
Your hands went to my forearms as I got into position over you, and you closed your eyes, only to open them again as I paused, the head of my cock pressing against your virgin opening.
I kissed you, deeply, passionately, as you felt my hardness split you open and begin to fill you. You whimpered as I pressed against your hymen, but you pressed into the kiss, and I felt your hips press upwards slightly as well. With a firm motion, I pushed past it, muffling your yelp with my mouth as we continued to kiss, and then was in you, fully and deeply, pressing my body against yours as the full length of my shaft filled you, the wiry hairs at my base tickling your shaved pubis.
I lay like that for a few minutes, enjoying the feeling of your intense tightness as you became accustomed to the feel of a man inside you properly. Then I began to slowly move, sliding out and then back home, pushing my hips to give some movement, but not a lot, this was a gentle coupling, gentle like my Boonie was gentle.
You began to move your hips as well, your body knowing what it wanted, even as your eyes remained closed, tears leaking from them as your emotions conflicted over what had happened. You were a southern belle, never really been kissed. Now you were a woman, after 28 years. Not married, making love to a man who you could never marry, enjoying a ‘dirty’ weekend with somebody you travelled cross the entire country to do this with so your parents would never find out. We made love the only way we could, with passion and tenderness.
I finally came into you, after you had reached two more climaxes with me firmly embedded in your depths, then I finished and unloaded my own seed into your body. After, I would not allow you to get up to clean up, bathroom only, then come back to the bed and curl up beside me, the evidence still on your thighs and buttocks, of our coupling and your lost innocence. You cuddled against me tightly, bottom pressed against my groin hard, my arms wrapped around you holding you in a tight embrace, and we slept.
Disneyland was fun, the best trip I ever had. Splash mountain was the best experience. Sitting behind my Boonie, hands firmly on her hips as the log ride spun and rushed round corners, up and down the flumes, rushing around. Boonie laughed as my hands slid under her shirt and gently cupped her breasts but did nothing to stop me, although I did withdraw my hands as the big drop came, because they took photos and it would not do for a photo to possibly end up back east for them to see their daughter having a strange man groping her on the ride.
After the day, back to the hotel, for another shower to wash off the sweat, then you wanted the spanking from me that was almost as much of a need as the lovemaking. I slapped your trim bare bottom firmly, smacking you all over your small backside, bringing colour to it even as you wriggled in discomfort. You had no real experience to process this pain into pleasure, so I was determined to help your body begin to process the emotions properly, as a woman should be able to do.
With my other hand gently caressing both breasts, rubbing nipples into an erect state, I pressed your legs apart and continued my spanking, fingers dipping in between as I did, teasing you and beginning to awaken lusts.
The spanking continued, bringing a pink flush to your bottom as my hand firmly slapped all over it, bringing a solid warmth and pink colour to your cheeks. Then I laid you on the bed and lifted your legs so that you held them under your knees, and I gave more attention to your bottom in the diaper position, so that my fingers could easily caress you intimately as your bottom continued to flush with colour and begin to take on a proper red shade.
It had begun to really hurt, despite the erotic caresses, and you began to kick and shift your legs, unable to handle the pain, so I stopped, pulling you up against me in a solid hug, and stroked your hair and cheek, giving you the affection that was important for any sub to know that despite the trial she had gone through, she was loved.
You had not cried yet, but then you began to, all of a sudden, shedding tears quietly, you were not a noisy girl by any means, and you quietly cried, holding on to me, naked, in my lap, as you cried, feeling safe, feeling protected, knowing that you were loved, knowing that this was what you had wanted and were getting it fulfilled, and that nothing would happen that you did not want to happen.
Your lips found mine and you kissed me with a passion that was not surprising, as the heat finally reached your pussy, slowly bringing it awake and letting the rest of you know, there was a purpose to the pain. I kissed you back, my hands caressing your breast and also rubbing your bottom as you sat on my lap, feeling the heat I had put there as you began to wriggle your hips against the fire slowly beginning to build in your loins.
Laying you back on the bed, my hands roamed all over you as my lips followed, kissing your neck, breasts, nipples, stomach, then my lips brushed your mons and found your small clitoris, then gently kissed it, making you gasp and writhe.
I gently kissed it, then kicked it as well, letting my tongue caress it in every direction, then I moved down and licked your lips and allowed my tongue to slightly move around the entrance to your vagina, making you gasp again and you pushed me away, unsure of the feelings I was bringing up.
“You didn’t want that, it was not part of your interest, although it felt good, it was not what you had imagined, and as a result, was not on the books for this weekend. You quickly scurried down and took me in your hands, the first time since we had become intimate that you got a good look at my package. Your hands were inexperienced, your mouth not much better, but bless you, me girl, you tried. You kissed all over, your tongue working overtime as you licked me frantically, then you took me into your mouth, licking and sucking noisily as you tried to do the right thing orally, to get me excited. It wasn’t necessary and after a little while, I pulled you off and gently laid you on your back again with a soft kiss.
You had almost instinctively spread your legs slightly when you laid back, and I took the opportunity to lay on you and slide into you gently, this time there was no extra lube, just your moistness and my excitement. I slid into you, then with a firm kiss on your mouth, slid fully into you, making you gasp as your almost virgin pussy expanded to accept me. I am not a big man, but decently thick, so I stretched you as I slid into you.
We fucked slowly but steadily, your legs slowly lifting up then wrapping around my waist as I slid in and out of you, your body responding to the movement as the excitement built inside of you, bringing you to a peak of pleasure that was heightened by your still very sore and red bottom.
I rolled and ended up with you on top, not what you expected, but as my hands were a firm grip on your hips, you knew that I was still in control, so the submissive role was still maintained. I lifted you slightly, so that you slid up along the length of my shaft, then you settled down on your own, eyes widening as you felt the full sensations that your action had done. You did it again, then again, trying to move faster, but my hands held you firmly and guided the pace.
I felt you begin to contract, and watched the skin flush occur as the orgasm began to peak in you, seeing the reddish blush rise in your chest and sweep up to your neck as you gasped and I felt the muscular contractions. I pulled you down hard on me as you hit your peak, you crying out softly and I quickly finished as well, spurting into you, helping you to continue the orgasm as I completed you for this time.
You snuggled up to me afterwards, not wanting to get up, ignoring the slightly uncomfortable feeling as my seed slid out of you, and we enjoyed the afterglow of the coupling. Then, another shower, and off to dinner.
That night, you wanted me to take you fully, which meant using you anally. This was the last part you wanted to have happen, and you actually wanted this first, as your deflowering had been too scary, but with me, you allowed me to take charge as the trust had been built so strongly that you felt totally at peace and there was no concern at all.
More KY jelly, this time after a long massage, where you lay naked on the bed, and my gentle hands rubbed, kneaded and caressed your entire body, front and then back, relaxing you, easing tension, and then I began to focus my attention on your bottom, kneading and working your cheeks as my fingers rubbed and caressed the cleft between your cheeks, lightly touching both your anus and pussy from behind, then continuing to massage you and keep relaxing you.
I took some jelly and began to rub it around and then gently, pushed it into your anus, allowing for you to relax and get used to my finger in you to the first joint, then I put more jelly on and added a second finger, gently moving them in and out. More jelly made movement easier as you expanded to accommodate me, and then I put a good dollop on my cock, rubbing it around to coat me fully, and shifted position so that I was at the entrance.
With a gentle but firm pressure, I slid into your tight back passage, you gasped and wriggled as my thick cock slid into you, but your well-lubed passage was prepared and I slid into you fully without much difficulty. You groaned as your anus stretched to accommodate my thickness, as well as my weight pressing down onto your hips and lower back.
Now that I was in you, I began to move, slowly but firmly, and you felt the feelings rise again, this time, more submissive sensations, you were being taken by your Dom, the way he wanted to, and you had no choice but to enjoy it, or suffer.
I rolled you onto your side, still deep in you, and you curled into an almost foetal position so that my arms could hold you fully, one firmly gripping your hips, the other holding your breasts and roughly pinching your little nipples as I continued to slide in and out of your bottom.
Your anus was very tight, and it did not take too long before I felt the urge to climax, knowing that I was not going to be able to hold it back, however, this was also part of what was your expectation, you cumming while I was using your bottom was not expected, you wanted to be dominated in this position, not pleasured. You wanted to be taken and used, and so you were. I came in you, filling your bowels with a load of sperm as I held you tightly enough against me to leave bruises on your hips.
After Disneyland, Boonie went back to the East Coast and although contact was maintained, it eventually began to fade as she found her new life, and my focus shifted to two new submissive girls in my life.
I had been mentoring a young lass by the handle of Londonkitty for about a year as she explored the D/s world with various different men, when she decided to make the decision to meet me. Although nothing overtly sexual happened, it was a series of encounters that left me satisfied and which I do cherish for the knowledge I gathered and for the pleasure I supplied her.
She showed up, tall, lithe, confident within herself, but still uncertain of what should happen and how to make it happen. We spent an hour talking about D/s and what it entailed, so that she was fully aware of everything. I told her right from the start, I would not be fucking her, and that the relationship would only be of a BDSM nature, with her learning the ropes and paddles, with her receiving orgasms and learning how to tune her body to enjoy the pain to pleasure process, but that she would not feel my cock in her.
Her first real D/s relationship had been a disaster, the Dom was abusive, would beat her entire body, and anally raped her when she disobeyed him. She eventually left him and in fact, changed her phone number to stop him pursuing her. It took some work from me and others in the community to protect her, but we achieved it, although I never took the time to learn his name or location, because I did not want to end up in jail.
Six months of regular meetings then ensued, with londonkitty coming over to my place and getting stripped, then her bottom spanked to her limits, and then a bit beyond in most cases. She was always cuddled afterwards, and in most cases, I then pleasured her to orgasm while her red bottom writhed on my lap.
For her, it helped a lot, because she learned what worked best to bring her to shuddering orgasms, and what did not work, so she could better guide her future boyfriends and Dominants to give her what worked best. A bare bottom spanking with hand or paddle while her wrists were tied would always bring her to a multiple orgasm, and as we experimented, we narrowed it down to the point where she knew exactly what worked and was able to use that to find herself a loving partner later on who she married and now has children with. She is very happy, and I am glad, she is a lovely girl and deserves only happiness.
If I ever found the Dom who had given her such a bad experience first off, I am sure I would have ended up being charged with assault after leaving him in a pile of bloody mess on the sidewalk.
My last girl was my kymbrgrrl. She was older than me, 42 to my 31, and we had a torrid affair that lasted until I left the country. She was living with her ex husband as he was disabled and she felt a sense of loyalty to take care of him even though she was no longer married to him. They had a child together, who was now living in another state, and she was eager to explore D/s with somebody.
I was lurking online as I always did after work, and she popped into the chat room, I had noticed the nick a few times before, and this time, she struck up a conversation. We discovered that she was only just up the road from me, not even a mile away, and with a brief chat in private, she took the plunge to drive down and meet for coffee.
Coffee, yeah right. This was unexpected, unsafe, passionate sex. You came into my living room, slightly afraid, not too sure what to expect. Kymbrgrrl was small, 5′ in bare feet, and thin, almost elfin. You stood in the room, looking around, looking at me, and not quite biting your lip, but still unsure of what was going on and what might happen.
I sat down and indicated for you to sit, you did, and we chatted about some things, then you professed that you wanted to be spanked, tonight. So I accommodated you. Who am I to turn down a pretty girl who wants to go across my lap and get her bottom coloured?
I undressed you slowly, exposing small breasts with long nipples that were overly sensitive, then slipped your pants and underwear down to expose a shaved pussy and a bottom that was just aching to be given attention.
As you stood, I slapped your bottom a few times, just to gauge reactions, then it was across my lap for a firm spanking. You began to cry almost immediately, and I knew, this was not a ‘normal’ reaction, there was something more to be gained. Slowly spanking you, my other hand slid around to your front and began to caress you, you came with my first touch, a shuddering climax against my hand. More followed, as kymbrgrrl was a multi-orgasmic girl who had never had a deep climax, just lots of surface ones.
I picked you up and walked into the bedroom, intending to give you some serious pleasure with my hands and mouth, and as I sat on the bed, you asked me to take off my pants so that you could give me some reward as well. I obliged, and you took me in your hand, bringing me fully erect, then I stopped you and was going to pull you down when you made the move to straddle me and I ended up on my back, you on top, my cock already just inside the entrance of your pussy.
I looked at you and asked if this was OK, not wanting to do anything you did not want, you nodded and pressed down, allowing me to fill you completely.
So began a torrid affair that lasted until Summer 2001. You had never taken a man anally before, that changed as I enjoyed all of your body, you enjoyed fucking me solidly, then slipping off and having me finish in your mouth as you swallowed my seed, enjoying the control and domination that was entranced in the relationship.
Things always change, and things made a change for the worse in the Summer of 2001. Baybe decided to run off across the country to find some Dom, and as she left, felt that I was not worth it any more, so informed US immigration on me. I had to leave the country and fast.
I received two offers within a few days, both BadGirl and boonie offered to marry me, as a means to keep me in the country. I could not do that to either of them, they had their own lives to live and what we shared was more of an infatuation than real love, even if love may have developed. I very gently declined both offers and made my way across the border to Canada, where I had citizenship and was safe.
Kymbrgrrl had already begun a relationship with the other man Baybe had left, Master Everett. He was a 911 dispatcher who she married, and he gave her so much joy and pleasure. He suffered from MS and she was dedicated to him, bringing him through his illness and difficulties, and saying goodbye after he retired from being a dispatcher and died of a heart attack not even six months later.
I kept in touch with people, but even that began to fade as I met the true love of my life, my Angel. To her, I was Dragon, and we have shared each other for the past eleven years now, still going strong. Her children accepted me as their Dad, so I got a full family in the bargain.
So, the life of TheOldDragon, began as an online presence on a spanking chat server, expanded into a reality full of love, companionship, sex and comfort, now ends with a life-long partnership, family to call my own, and a loving partner who I am dedicated to and who has never cheated on me, nor me on her. Life does work out, in the end, sometimes, you just have to slog through the mud to get to the pasture.