21 years 42 strappings
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Dallena Does Strap On free porn video
Hi, ISS Readers, This is Dallena again. Find below is my new story. Your comments & replies are welcomed at When I was 25, I worked in a local office as an Admin Assistant. I worked for Jasmine who was the secretary of the office manager, Dallena. My job was to help her sort out the backlog of paper work left after her last assistant had walked out on the job. Jasmine was in her mid-twenties with a gorgeous trim body but a dull character. Her main topics of conversation were her husband, their cats and the ‘exotic’ package holidays they treated themselves to every year. I soon found myself saying yes, no and lovely at appropriate moments and letting my mind drift.
After three weeks, I came in on Friday morning to find I was covering for Jasmine for the day as she had rung in with a migraine. I got my head down and tried to do as much as I could. Dallena turned up at 10am and called me into her office. She told me that I should not try to do everything and gave me some priorities. It was the first time I had spoken to her and found myself warming to her straight away. We struggled on, staying late into the evening, as everything seemed to be at crisis point. I began to realize why Jasmine had a bloody headache. At around 11pm Dallena said we should call it a day and asked if I wanted to go for a drink. I pointed out that the pubs were all closing and it would mean going to a nightclub. Dallena immediately suggested that I come back to her place for a drink as she only lived five minutes drive from the office. I took her up on the offer and we headed to her flat. An hour later, we were deep in conversation on her couch, a glass of wine in our hands. We had started off with small talk about what I was studying and what my plans for the future were. Talk turned to boyfriends and I decided that I would see how shakable Dallena was by telling her that I was bisexual and my last boyfriend was a girl. She raised her eyebrows then smiled and told me that she had given up on men after two failed relations and was a lesbian.
The atmosphere changed, as we looked at each other in a new light. Dallena was in her mid-thirties, still trim but starting to soften slightly. She has long, dark brown hair that I had only ever seen tied up at that time, a round face with a hint of a double chin, dark brown eyes and full lips. She was taller than me at 5’ 7″ and her boobs were large and full. Her stomach was fairly trim but her hips were quite wide. Her legs were her best feature. Long and well shaped, they had been the first thing I had noticed when I was introduced to her as she was wearing a long wrap around skirt that had fallen off her legs as she sat down in front of me, giving me a glimpse of her stocking top. We looked at each other for a moment, appraising each other. I broke the silence by asking if she was seeing anyone. She laughed and said she had several girlfriends who came and went at her beck and call. I assumed she was joking and laughed saying she was the first Mistress I had met. She looked me in the eye and said that she did not consider herself to be a Mistress as she wasn’t into domination full time but went on to tell me about her roll playing games. I listened as she described how she liked to relieve the stress of work by getting her girlfriends to dress up as secretaries and come to the house as if it was a place of work. She would then punish or seduce them depending on her mood and the events of the previous week at work. She admitted that when she did this she often fantasized that it was Jasmine or I being punished. I was a little shocked at the revelation and a little flattered too.
We talked about the kind of things she liked to do and how she had discovered herself. I was intrigued and finally asked if she would let me play one of her games since she had already included me in her mind. She thought for a moment and said that she would love to but I had to be discrete at work. It was something new that I hadn’t tried before and I wanted it so badly. Finally, Dallena agreed that she would trust me. I asked her how she wanted to play it and she said she was too tired to get into it now. We made a date for the following evening and I left. Sofia quickly wrote out what she wanted me to wear and what my role would be when I got to her flat. I read the piece of paper five times in the taxi on the way home and had to masturbate twice before I could sleep.
The next day I busied myself around the house, interviewing a new lodger for the downstairs bedroom. My mind was not on what I was saying, especially as the girl who had come about the room was wearing a business suit having popped round from the estate agents where she worked. At 7pm, I was dressed in a short, pin stripe skirt, black tights, strappy heels and a silk blouse. I contemplated wearing some nice underwear but Dallena’s letter had warned me that I was to wear underwear that I would normally wear at the office. The drive round to Dallena’s didn’t take long and before I knew it I was ringing her doorbell. I was Anupama the secretary and I had been summoned to the boss’s office to discuss my future with the company.
Dallena answered the door in a dark, tailored power suit. I followed her through the flat and into one of the bedrooms. The bedroom had been set up as an office, similar to Dallena’s office at work. A large desk had a computer on it and a leather swivel chair behind it. To the right of the door was a couple of filling cabinets. Sofia took her jacket off and motioned me to sit on the chair in front of the desk. As I sat down, demurely pulling my short skirt down, crossing my ankles and putting my hands in my lap, Sofia took her place opposite me.
‘Anupama, you have worked here for three months and I must say that your work is very good. However, you’re dress leaves a lot to be desired. The men in the office are not working as hard as they once did before they spend all day gazing at your legs and trying to look down your loose blouse.’ she began.
I instinctively looked at my loose blouse and saw how much cleavage I was showing. I tried to cover myself up but Dallena got to her feet and moved to the front of the desk.
‘You might try to cover yourself up young lady but it’s too late now. The damage has been done.’ she snapped then continued in a more menacing tone, ‘I also have reports that someone is rumored to be having an affair with our Sales Manager, Rakesh. The rumors speak of illicit sex in the photocopying room after working hours. The rumors have been linked with your name Anupama. What do you have to say for yourself?’
I looked into her eyes, saw a lustful gleam and decided I was going to play a defiant, cocky roll.
‘Some might say that Rakesh is fucking a younger woman because a certain manager in our office is too frigid to allow herself a little pleasure’ I answered back. Sofia looked shocked at my retort. Or acted shocked. She told me to get to my feet, which I grudgingly did. Dallena walked to her desk and picked up a piece of paper. This is your employment contract. You signed this when you first started with us. It says that a senior manager is entitled to punish a junior member of staff if the junior member of staff breaks any of the company’s rules. You have broken one of those rules… no fraternizing between members of staff on work premises.’ she said in an official sounding voice, ‘ your punishment is to be spanked by a senior member of staff, the amount of strokes and method are defined in the company handbook. In your case, you may choose between 50 smacks with the hand, 20 strokes with a strap or 12 strokes with a cane. Which do you choose?’ I looked at her and wondered what to go for.
‘I’ll take the 50 with the hand’ I mumbled. Dallena said that was fine with her. She moved the chair I had been sitting on out of the way and told to bend over the desk. I moved over and leant over so that my upper body was on the desk with my bum stuck in the air. I was highly aware of how submissive the pose was and how horny I was getting. Dallena stood to one side then pulled my skirt up.
‘What are you doing?’ I yelped
‘The rules say that for a first offence the spanking must be made on underwear. A second offence will result in the punishment being administered to your bare bottom. Didn’t you read the rules before you signed them? Well, it doesn’t matter. You can’t be punished for stupidity yet.’ She continued pulling at my skirt until it was pushed up to my waist. My bottom felt cold sticking out behind me even though my panties and tights covered it. Sofia stood to one side of me and I braced myself. The first smack landing in the middle of my right cheek, stinging but not that painful. The second followed it on my left cheek, a little harder than before. A tingle started between my legs as Sofia continued to spank my bottom, alternating between cheeks, always hitting the fleshy part of my buttocks. By the time she had done 25 strokes, I could feel a warm glow on my bum and between my legs. I was dying to put my hand between my legs and touch myself but couldn’t. Dallena continued spanking me, her slaps getting harder until the last 10 when she really let go, five of the smacks landed on the tops of my thighs which hurt but sent a massive shudder through me. I shouted aloud as each landed. When she had finished telling me to stand up but to leave my skirt where it was. We were both breathing heavily but for different reasons. I stood looking at the floor as she stared at me. She walked to the desk and picked up the phone, pretending to dial a number. I heard her having a pretend conversation with someone else in the ‘office’, her responses getting more and terser as she went on. I looked up and saw her looking at me with anger and a little contempt.
I wondered what was going on at first then figured that the role-playing was far from over. I was glad about that because I had just started getting into it and, looking at Sofia’s flushed face, so had she. I admired her heavy tits as they moved up and down with her breathing. I figured she wasn’t wearing anything more supportive than a camisole top and hoped to find out for myself later. Dallena put the phone down firmly and turned to look at me ‘I’m afraid we’re not finished yet young lady. I have just been informed that not only did you have sex with Rakesh in the photocopying room; you were also seen having sex with one of our most important clients in the public toilets in reception. As this is your second offence the spanking will be on your bare bottom and this time you will receive another 50 smacks on with my hand and 6 lashes with the strap’ I swallowed hard and looked into her eyes. I could almost feel my wetness running down my legs. This was so hot and I so wanted to rip my clothes off and throw myself on Dallena’s mercy. I leaped on this and decided to role-play it.
‘Isn’t there anything I can do for you that will limit my punishment?’ I asked, almost in a whisper.
‘And what do you think I could want from a slut like you?’ was my only answer. ‘Please, I’ll do anything you want. Anything. Those men just led me astray. I thought I was doing my best’ I sniffed, pretending to cry. ‘OK, I’m not the heartless bitch everyone thinks I am. I have to punish you, it’s the company rules, but I can reduce your punishment if you do something for me. I will think of something to do while I finish the rest of your punishment. 25 smacks with my hand and 4 strokes with the strap’ Dallena led me through the familiarity of her living room and into her bedroom. It was tastefully decorated and dominated by a large iron framed double bed that sat quite low to the ground. I briefly wondered how many women had been tied to it since she moved into the flat. Sofia sat on the edge of the bed, her skirt riding up her legs a little. ‘Come here Anupama.’ She said, slightly more gently than before. I stood to her right, my skirt still up around my waist and my pussy moist. My bum was still warm and I was almost weak with anticipation. Dallena turned to me and pulled at my tights and knickers until they were down around my thighs. She briefly examined my pubic hair then bent me over her knees, moving my position until she had my bum where she wanted it. All I could do was grip her lower legs or her low-heeled shoes. My legs dangled slightly behind me. My naked bum and pussy felt cold and exposed.
I felt Dallena’s hands moving over my bottom, pulling and pushing the cheeks, then a hard smack on my right cheek. This was as hard as the last 10 I had received over my covered bum and stung. I yelped and asked her to be gentle. The next smack hurt as much as the first. Dallena’s left hand went to my back and pushed me down. ‘Grip my legs Anupama’ she ordered. I wrapped my hands around her stocking calves, my hands automatically caressing them just before the third smack landed across my bum. My cunt felt like it was on fire and my bum was stinging like crazy. I gripped Sofia’s legs, feeling the nylon move under my fingers and tried to brace myself. The next seven slaps landed in quick succession and I cried out again. Sofia rubbed my bum again, her fingers delving into my crevice, rubbing my anus then down over my pussy. ‘So, you are a horny little slut then Anupama’ she said then smacked each cheek and the tops of each thigh. Again, I screamed and got the same thing again for my troubles. I had lost count. I didn’t know how many more. The rest of my spanking was a blur of stinging pain and jittery feelings up and down my legs and spine. When Sofia had finished, she caressed my bum until my breathing returned to a more normal pace. I realized that the sensations I had got from the punishment were very similar to an orgasm. I had been reading about piercing and endorphin rushes and realized that was what I must have experienced. Dallena’s fingers started between my legs and I naturally moved my legs apart for her.
‘Oh no, no pleasure for you little slut. Not just yet’ she laughed. She made me stand up and bend over the end of the bed, telling me to grip the iron bedstead. She said she would try to make the strapping as easy as possible. I looked behind me to see Sofia pulling her skirt off. She was wearing black stockings and a pair of ivory, silk French knickers. As I watched her, she removed her blouse to reveal a matching ivory, silk camisole top. She folded her blouse and placed it on a chair then picked up a leather strap from the floor. I braced myself, trying to judge when the blow was coming so I could move my bum forward but she was too good at anticipating my movements and all four lashes landed squarely on my arse. The strap stung a lot more than her hand but it was still a good hurt. When she had finished, she told me to stand up. I stood before her, my sex on show for her eyes. She told me to take my skirt and blouse off, pull my knickers and tights back up. When I had done that she slowly walked over to me, walking around me while looking at my body, occasionally running her fingers over part of me. She reached for my bra strap when she was behind me and deftly unfastened it. I let it fall to the ground without moving. She moved around me so that she was facing me again and reached out for my right nipple. She pinched it hard between her thumb and forefinger, pulling me to her. I moaned and moved towards her. She continued moving backwards, pulling me with her by the tit and then letting me go when we reached the bed. She reached down and pulled her knickers down, then sat on the edge of the bed.
‘Have you ever licked a woman’s pussy Anupama?’ she asked. ‘No, never’ I said, the note had said I was purely hetro. Dallena opened her legs to show me her pussy. Her clit and lips were shaved clean.
‘Kneel before me Slut’ she said, ‘you are going to eat me and you are going to make me cum or you will be caned. Is that understood?’ I meekly replied that it was and knelt in front of her, moving between her legs until my mouth was hovering over her plump cunt. Dallena pulled her legs up and rested them on my shoulder kicking her shoes off in the process. Her right leg bent around my head and pulled me into her sex. I began to lap at her, running my tongue over her wet lips and up to her clit. I soon figured out what she liked and went to work. Her right leg remained hooked around my neck; keeping me working at her while her stocking left foot rubbed my shoulders and back. It took me around five minutes to make her cum, when she did she almost suffocated me with her pussy as her leg pulled me into her in spasm. I extracted myself and stood at the side of the bed looking down at her heaving body. She smiled up at me and said I had done very well and earned my reward.
She got off the bed and told to strip naked and lay on my stomach on the bed. I complied with her wishes, trying to look at her when I heard her rummage around in a drawer behind me. ‘Anupama, look at me’ she whispered softly. She was naked except for her stockings and a seven-inch dildo strapped to her groin. Her big, soft tits were rising up and down with her excitement. Her nipples were rock solid.
‘You may play with your clit while I fuck you little slut.’ she said. I pushed my hand underneath my body until my fingers were around my clitoris. She moved over me, sitting astride my thighs. The black cock resting between my buttocks, she lifted off me and pushed the dildo between my legs, impaling me on the black rubber and sliding it all the way into me in one push. I gasped as she immediately pulled out and slammed it back into me again. I could feel her tits swinging, her nipples brushing against my back. She continued fucking me like this for a minute then slowly changed her position so she was lying on top of me, her upper body weight resting on her elbows. I spread my legs behind me and felt her move her legs together inside mine. Her heavy breasts pushed into my back. She started fucking me slowly, kissing the back of my neck and my shoulders. I played with my clit and pushed back against her with my bum, trying to rub my legs against hers. She increased the tempo of her hip thrusts until she was slamming the dildo in and out of my pussy, her weight bearing down on me. I could hear her heavy breathing in my ear and started to match her breaths with mine. She started whispering in my ear, calling me a slut and a whore. Telling me how much she enjoyed fucking little office sluts with her black cock. I came, the orgasm building up slowly. She groaned in my ear and I felt her body convulse on top of me… It sounded like she had made herself cum with me.
I felt her weight lifting off me, her hands rubbing my back and bum. I slowly rolled around to look at her. She was undoing the dildo from her body. I watched as she pulled the strapping off then slowly pulled the second part of the dildo out of her body. The strap on was designed so that a fat round cock was inside the wearer and rubber nodules tormented the clit as the strap on was used to fuck someone. Dallena collapsed next to me and we hugged each other, our hands gently caressing each other. ‘Did you enjoy that little Slut’ she asked. I replied that I had and that I wouldn’t be shagging anymore men. We kissed for the first time, our tongues finding each other’s then we moved under the bedclothes and slept. The next morning I woke to find her standing at the end of the bed looking at me. She was dressed in jogging bottoms and a tee shirt. I could see from the way she was moving that she didn’t have a bra on. I smiled at her and asked her if she was OK. She replied that she was but she was horny and was about to wake me for sex. I laughed and said that she didn’t pull any punches. Dallena climbed on the bed and said that she wanted me to do all the work as she had worked so hard the night before. She got on her knees and gripped the end of the bedstead. I moved behind her, running my hands over her legs and bum, then over her back to her hair. I pushed my hands inside her tee shirt; cupping her tits and feeling her nipples harden in my palms. I stood over her from behind and pulled her mouth to mine. We kissed for a minute or two, and then I dropped to my knees behind her. ‘Are you staying in that position then?’ I asked.
‘Yes, I feel like being on my knees this morning’ she replied, resting her head on her arms. I reached for the waistband of her jogging bottoms and pulled them down off her bum. When they were down to her knees, I reached underneath her to feel her pussy. She was moist but not ready for penetration. I dropped down behind her, pulling her thighs as far apart as the jogging bottoms would allow then started to tongue her slit, running my tongue down between her labia to her clit then back as far as her anus, licking this gently then making another circuit of her sex. I continued doing this gently, teasing her for a couple of minutes, then gently inserted a finger into her cunt. She moaned with pleasure as I gently moved my finger inside her, playing with her clit with my other hand and running my tongue around her buttocks and over her arse hole. Slowly I pushed another finger in, then another and finally a fourth, spreading them out inside her, trying to stroke her in as many different places at once. My finger worked harder on her clit, my tongue slowly pushing its way into her anus. She shouted aloud as I folded my hand and pushed my fist into her fat cunt. I stopped playing with her clit and told her to pull her tee shirt off. She quickly did this and bent over for me again. I grabbed one of her tits and started pinching the nipple between my thumb and forefinger, moving my fist in and out of her. ‘Where did you put the strap on Dallena?’ I asked her, a new idea forming in my mind. ‘Second drawer down, over there’, she replied, pointing to a chest of drawers in the corner.
I pulled my fist from her cunt, licking my fingers as I walked over to the chest of drawers. Sofia watched me and smiled as I looked back at her to confirm the correct drawer. I opened it up and saw various sex toys. The leather strap that had stung my bum the night before, the strap on dildo, a double-ended dildo that was designed for simultaneous vaginal and anal penetration, plus assorted sizes and shapes of vibrators and dildos. I picked up the strap on; a long thin vibrator and some lube then closed the drawer.
Sofia had removed her jogging bottoms and was lying on her stomach on the bed, watching me examine the toys. I was just stepping into the harness of the strap on when Dallena said: ‘Anupama please put your tights on first then put it on. I love the feeling against my skin as I’m fucked’ she said dreamily. I found my tights and pulled them on, making sure Sofia watched me. I pulled a hole in the crutch so the dildo could go inside me. I pulled the harness on, pushing the fat, rubber cock inside myself. It was only five inches long but very thick and felt wonderful as I strapped it in place. As I walked across to the bed, I could feel the cock moving inside me, the rubber petals inside the harness rubbing my clit. Dallena resumed her position on the bed, this time gripping the bottom of the frame. I grabbed a stocking from the chair as I passed and leant down to tie her wrists to the frame.
‘Now you can’t get away from me and I can have my wicked way with you’ I said, slapping her arse with my hand. I knelt behind her again and put my hand to her pussy. She was still dripping wet. I began to massage her cunt with one hand and her anus with the other, rubbing lubricating jelly deep inside her arse hole with a finger. Her cunt needed no lubrication. I moved behind her so that the dildo was pushing against her cunt, the end slid inside her easily. I stopped when the first inch was inside, teasing her with it. ‘Anupama, fuck me. Please fuck me hard’ she gasped. I slapped at her buttocks telling her I would fuck her when I was ready. I switched the long thin vibrator on, feeling the intensity of it by pushing it against my nipples. The vibes made my nipples harden and I felt a familiar warm feeling in my groin. I slowly pushed the vibrating toy into Dallena’s arse, asking her if she liked having her arse penetrated. She moaned and thrashed around, trying to get the larger cock into her cunt but I held back, slapping at her arse if she got too frisky. Slowly the vibrator disappeared into her anus, smoothly running in until it was buried in her. I pulled it out so the tip was just resting on her puckered anus and pushed it all the way in again, pushing my hips forward and impaling her on the strap on cock. She screamed and I began slowly fucking her cunt, rubbing my nylon-clad thighs against the backs of her legs. She pushed her bum against me, fucking me back as I pushed into her. I was slowly fucking her cunt and slamming the vibrator in and out of her arse as fast as I could. The rubber petals on the harness were just in the right spot and I was really getting off.
My knees began to cramp so I pulled out of Dallena, leaving the vibrator stuck in her arse, and stood above her. Squatting down over her, I reinserted the dildo and began to fuck her harder, again moving the vibrator in and out of her arse. She moaned, bucked and shouted aloud as the first orgasm hit her. I pulled the vibrator out of her arse and lay on her back, pushing my hands in front of her and squeezing her tits hard, occasionally slapping the sides so they wobbled underneath her. I slammed the rubber cock into her, pushing the inner cock hard into me and rubbing my clit with the harness. I was breathless by the time I came and Dallena was almost hysterical. I slowed down, leaving the cock in her and kissed her shoulders and back. Slowly I pulled out of her and pulled the harness of me. I untied Dallena and we lay in each other’s arms, gently kissing each other. We thanked each other for a wonderful weekend and I left around 2pm with another of Dallena’s role-playing notes. This one dictated another meeting in a week’s time. I could hardly wait. I love feedback good or bad as long as it’s honest. Send all feedback to the link below. Please make sure you put the story title in the subject line so I know it’s not spam.
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