The kids were off seeing the grandparents for the day – who was I to deny them opportunities to spend time together? And my wife, Penny, had said that she had a few things to do – nothing that I could help with. I ran through in my mind if there was anything that I needed to do and figured there was some work that I could get done. Heading down into the basement where our office was, I hopped on the computer and started to get some stuff done.
I had been working away for a while – somewhat seriously, I wasn’t busting my butt by any means, when I heard Penny coming down the steps into the basement. Without turning around, I called out “Hey honey, what’s up?” She didn’t respond right away, so I just finished up my thought in what I was doing and then turned around. What a sight greeted me.
I started at the floor and moved my eyes upwards. Penny was wearing her black high heels, opened toe, so not my favorite, but a good tall heel on it, which was. On her legs she wore her black stockings. My oh my, did I love stockings. Not her black fishnet stockings – which were fun as they had elastic tops, but her regular ones. I wondered how she had them clipped up. I was sure that I would soon find out. Her skirt ended a bit above her knees, it could be classified as sexy but not quite yet slutty. It was tight, but not too tight. It was darker in colour with a nice pattern on it. Her top was lacy and white, buttoned up the front. On her wrists were some glittering silver bracelets and her neck sported a necklace to match it. Her hair was up. She was walking towards me holding a pen and a notebook in front of her. I felt myself getting rock hard. It had been years since she last did what I thought she was about to do. I wondered why on earth I was going to be so lucky today.
As I swived in my chair to fully face Penny, she came to a stop before me and asked “Hello sir, I’m your new secretary. I hope that you find me up to whatever you need me for. I know that we are married, but I hope that you can see me as your good little secretary here at work.” She said her line, full of its double entendre, blushing and looking unsure of herself. We had tried a little bit of roleplay in the past, but she had never felt like she was very good at it. I wondered what had inspired her? Perhaps it was the encounter we had a few weeks ago, when we had a “three outfit night”. Perhaps that had helped her to realize that new things could be great fun.
Looking up at her, I knew that it had taken a lot of courage for her to start up what we were doing, so I was going to respond in time. This little bit of roleplay could be great fun. “Thank you Ms. Penny, but I have to be honest, your hiring caught me off-guard. I don’t think we ever had a proper interview to fully explore what talents and abilities you bring to me”, I responded. She wasn’t the only one who could do double entendre. Looking over, I decided to take a risk. “One thing though, we do record our interviews here, so that it can be examined later to help us make the best decision. Don’t worry about it, it’ll be off to the side, you can largely just ignore it.” Penny gave me a shy and nervous smile at this, but didn’t complain as I picked up the digital camera I had seen sitting to the side, and set it up in the corner of the room, giving it a great view of my desk and the area around it. Before I started the video recording, I said “Ms Penny, if we could not start from the top? To get everything on record.”. Clicking record, I went back and sat down and with much more confidence, Penny repeated her first line.
“She Ms Penny, what can you offer me?” I asked. With a slight hesitation, Penny replied “Well I file, keep track of your emails and well…. I am pretty good at taking dictation”. As Penny said that last word, she mouth turned up in a small smile. Oh good golly, this was just getting better and better. Smiling wide, I replied “Well that sounds rather lovely, but as a member of this company, you will be representing this company, so could I please have you show me what all will be representing us?” As I said this, I motioned for her to turn in a circle. “Do you think that’s appropriate? I thought that this was a professional environment!” She exclaimed. Putting on my best stern voice, I replied “Ms Penny. If you truly want to be my good little secretary, you’ll find that you need to find my orders to the letter. Since this is your first infraction, I’ll let it go, but in the future be warned that I will need to assert my authority if you do not comply.” Again, I motioned for her to circle.
Penny looked a bit more nervous at this, but did as I asked, and turned awkwardly in a circle, showing herself off to me – and the camera – from all angles. “Ms Penny, if you are to work here, you will need to show some more enthusiasm. We need to be represented with a smile and poise.” Penny looked confused for a moment, and then gave me a smile. This time she gave a much more graceful turn, pushing her chest out and smiling large. “Good girl” I responded. Penny’s smile grew at this statement. She loved being called a “good girl” – which was ironic because I called her that when she was being what could be very well considered a ‘bad girl’. I gestured to Penny that I would like to further what she had to offer me, a carry-on movement of my hand. “Oh, is there something else you would like to see?” Penny asked. But as she did so she put her hands behind her butt and pushed her chest out, clearly showing me what else she had to offer. I gestured with both hands out and open, indicating that I would love for her to show off for me. “Oh, I don’t know what else I have to show you!” Penny said, and as she did, she passed her pen to the hand holding her notebook, then, with her free hand, reached up and unbuttoned her blouse till a clear amount of cleavage was in sight. In fact, the edges of her bra were also available to see. Just as I was hoping that the camera was seeing this as well, she twisted on her toes, giving the camera a great look.
“I’m really not sure what to show you… here, let me put down these things for now.” As Penny said this, she took a step forward, so that she stood right in front of me, and then turned around, presenting her ass to me and the camera. Then she bend at the waist, keeping her feet together, and leaned much further down than necessary and placed her pen and notebook down. I couldn’t help myself, I ran my hands up her legs and got them just under her skirt when Penny squealed. “Excuse me!” She exclaimed as she stood quickly back up. “Bend back over Ms Penny.” I said sternly “I thought I was perfectly clear that I wanted my orders followed to the letter.” Penny looked over her shoulder at me, unsure what to do. I put my hand on her back and gave firm pressure. “Bend back over Ms Penny.” This time, Penny followed my command, sticking her ass back ever further than she had the first time. “Good girl” I replied “But apparently not always” I added on. “You will be punished for that infraction… in good time”.
As I told her this, I returned my hands to her legs, and ran them up her legs again. Stopping as they got under her skirt again. I massaged her thighs a bit, then ran my hands down her legs again and then ran them back up again, this time as high as I could get them. As my hands climbed higher, I felt the edge of her stockings, then the straps that held them up. My fingertips could then feel the garter that topped it all off. But one thing I did not feel – panties. I was so happy that Penny had learned how she was to properly dress. That being said, I knew how to roleplay this. I massaged her ass with my hands and as I did so I ran my thumbs towards her center as much as I could. “Ms Penny, I’m starting to see what sort of secretary you wish to be. Luckily that’s exactly the sort of secretary I’d always wished you would be.” Penny’s skirt rose higher and higher as I played with her ass and her feet came apart to keep her balance. As her legs came apart, it gave me more room. Penny gasped as my thumbs swiped her pussy. “That being said, showing up first day to the office, coming to your boss dressed as you are with no panties on? I must say that sends a certain signal.” “Well, I am your sexretary” Penny really emphasized the first syllable of that. “And as I told you, I want to be your good little sexretary”. Again, she emphasized that lovely first syllable. That being said, she said it rather breathlessly, as I was not letting up on her pussy.
By this point I had Penny’s skirt pushed right up around her waist. I reluctantly removed my hands from Penny’s rear, and leaned back admiring the view. I instructed Penny to shuffle her feet slightly so that she gave the camera a better view. I let her stay leaned over for a few seconds before I let her stand up. “Drop your skirt – I hardly think it necessary anymore.” I instructed. Penny didn’t turn around to comply. She reached around and unzipped herself. Then she did that lovely shuffle that women can do. Her skirt fell to the floor with a push from her hands and a slight bend of her knees. I then reached forward and tapped her legs, getting her to spread her legs apart. I shuffled sideways, as to not block the camera’s view and then used my hand to put gentle pressure on her back to get her to bend over again. I reached over and started to play with her pussy once again. Penny’s pussy was really quite wet by this time, my hand was getting quite slimy. I had my fun for a bit, getting Penny moaning considerably. To finish off, I stuck two fingers up into her pussy and sawed in and out a few times – meeting virtually no resistance. “A drenched pussy – clearly a sign of a good little secretary” I commented. “Your copious juices have simply drenched my hand.”
Penny turned around with a look on her face that I could not quite place. She looked at me for a while and then finally said “Well, part of a good secretaries job is to keep her boss comfortable, stress free and looking good”. My brain went blank as what Penny did next. She reached out, took my hand, bend at the waist once more and starting sucking my hands clean of her juices. She had never done anything close to this before – she thought that giving me a blowjob was disgusting enough and that for me to go down on her was just another level on top of that. I guess our 3 outfit night had changed her more than I had thought. She started with tentative licks, but these got more energetic and she finished with sucking each of my fingers clean as if they were all little cocks. When she was done, it was all I could do to say “Good girl.”
She stood back up straight, legs still apart with a slightly triumphal look on her face. I beamed back at her. Gathering my senses, I gave Penny her next command “Face the camera, keep your legs apart. Keep your back straight and your chest pushed out.” I wanted her on display for the camera. Penny complied instantly, and she crossed her arms behind her back to further emphasis her chest. Penny looked lovely, tits out but still concealed and pussy framed by her stockings and garter. I let her stand there for a few moments before I mindlessly ran my hands over what I could reach. Then I asked Penny to do something that I had never seen her do before and I seriously wondered if she had ever done before. I had asked her to play with her breasts before, but this was going to be new. “Reach down and play with your pussy.” Penny looked over at me with concern crossing her face. It was quickly replaced with a tiny moment of composing herself, but then just as quick as those emotions crossed her face, they were replaced with a genuine smile. This girl had truly learned about the joy of sexy play with her husband.
Penny placed one hand on her thigh and the other slowly reached to her pussy. At first Penny just slowly and carefully rubbed her pussy with her hand. Back and forth, then up and down. Penny kept going in this manner for a while, getting used to the feeling of her own hand upon herself. I started to hear how wet Penny was – there was a distinct sound that was coming from her obviously very wet pussy. And beyond that, the smell of her sex was clearly in the air now – the office was permeated with it. As Penny got into it, she changed up how she was playing with herself. Penny changed up from simple rubbing the entirety of her pussy, she made a small but important change. I saw her fingers middle two fingers part and she lightly gripped her clit between them. She continued to rub up and down but clearly this was something that bought her greater pleasure still. I sat entranced as my wife started to breathe heavier and heavier, her legs getting more bent as she fought to stay standing. Her hand on her thigh now there to hold her up. I couldn’t help myself, I started to rub myself – this was hot beyond imagine. Soon Penny changed it up again – she began to focus on her clit exclusively. First she rubbed it with just two fingers, but adding a third quite soon. She clearly was getting lost into her sex-filled mind, because her other hand left her thigh and with great difficulty, she completely unbuttoned her blouse. As soon as that was done her non-pussy hand started to maul her own breasts. She clearly didn’t think that she had enough access to her breasts, so she took a moment to completely shed her blouse.
“Finger yourself” I commanded. Without hesitation Penny quickly moved her fingers from clit and, bending a bit, slid two fingers into herself. She quickly learned that her thumb was now in position to play with her clit, so she made good use of that fact. Her fingers were not penetrating her at quite the rate I wanted so I directed her to speed it up. Besides the obvious effect of looking awesome, this fingering had the effect also of spreading her juices all around. These juices had already started to leak all down her leg, but now it seemed like they were just all over Penny’s lower half. Occasionally I would tell Penny to slap her pussy. First time she looked at me strangely, but then pulled out her fingers and gingerly slapped her pussy. “Harder” I commanded. Penny slapped a bit harder, her pussy made a wet noise and Penny made a “mmmmmmm” sound. “Once more”, Penny complied, more noise. Then I allowed her to get back to fingering herself. I had her do this a few more times after she had sawed into herself a bit. It was fantastic to watch Penny saw into herself. By the tone of her moaning, I could tell that Penny was getting close to cumming – I didn’t want this quite yet so I commanded her to stop. She gave me a very pained look… but complied. I reached over and with two fingers did a long swipe from just above her stocking top all the way up till I finished by swiping up her pussy’s slit. This brought forth a guttural deep moan from Penny. I brought the fingers to my own mouth and enjoyed my first taste of Penny’s juices. I indicated that Penny should clean her own hand as well. Penny, with glazed eyes, looked down at her own hand and slowly licked it clean. I wasn’t sure if she was doing it because of her sex haze or if she was trying to (further) turn me on, but her slower pace was amazing. The slow long suck of each finger perhaps was the best.
By this point, I had my cock out – how could I resist? Also, seeing how much fun Penny had just had, I decided it was time for a bit of enjoyment myself. “Ms Penny, thank you so much for showing me what you have to offer. I must say that I am more than pleased with what you have to bring to the table.” Penny looked at me a bit puzzled, I think she of momentarily forgot our roleplay. Snapping back into it, Penny straightened up and pushed out her chest. “Thank you sir” she replied. “I think now’s the time to put some of your skills to the test. If you will….” As I said this, I scooted away from my desk and motioned underneath it. I continued saying “You said that you were good at dictation – I think that it’s time to test that”. With a smile, Penny walked over passed me, kneeled to the ground and then backed under my desk. I stood up and moved over to the camera. No point in having it if it couldn’t record the action properly. I quickly attached the camera to the tripod that was nearby and had it look over my shoulder if were to be sitting. I then filled that position and before I had a chance to say anything, my cock was in Penny’s mouth. Penny went at my cock with a vengeance – kissing, licking, sucking… it was glorious. It was as if she was literally starving for my cock. As much as possible I made the pretense that I was working, but the wet blowjob (the best kind of course – the wetter the better) that I was getting was making that near impossible. Finally I just leaned back and enjoyed the show that Penny was giving me. Penny was really into the blowjob, moaning and generally being rather energetic. But I am nothing but generous so I instructed Penny to start to masturbate herself again. This lead to an even MORE wet and energetic blowjob. Leaning back I could just add my moans to Penny’s.
Eventually I knew that I couldn’t last much longer, my cock could take only so much awesome before I exploded! It took a feat of willpower, but I rolled backwards on the chair, my cock sliding from Penny’s now complaining mouth. She complained more when I told her to stop masturbating. “Shush, or I’ll have to punish you, Ms Penny. Now up you get. Feet apart, chest out, arms behind you back.” Penny complied quickly – in some ways, I was a little bit disappointed – I wanted to “punish” her a bit, she seemed to enjoy it so much during our 3 outfit night. As Penny stood tall, I stood next to her and inserted a couple of fingers up into her pussy. Penny shuttered. I prodded in and out a few times and then removed them. I then walked over to the camera and brought my fingers up to the lens. Slowly separating them, I showed the camera just how wet and sticky they were. Walking back to Penny I fed my fingers to Penny, enjoying as her tongue played with my fingers as they were in her mouth. As I pulled them out, they made a satisfying ‘pop’. Quickly repositioning the camera so it had the chair most central, I sat down and pulled Penny onto my lap. I had her facing towards the camera and she immediately grabbed my cock and directed it into her warm and wet pussy. It slid in without any resistance. As soon as I had entered her fully, Penny was bouncing back off, then driving herself back down onto my cock as far as she could go. She leaned forward so that she could really use her legs to fuck herself onto me, placing her hands on my legs for support as they were in between her own. I took the opportunity to unhook her bra – it was a bit difficult considering how active she was being, but I managed. I pushed the straps off of her shoulders and it held for a bit, but the sheer amount of movement that Penny was doing caused it to quickly fall. Normally, I was the one who did most if not all of the work when we had sex, but today really seemed to be different – Penny simply could not get enough cock into her fast enough.
I grabbed Penny’s hips and helped her drive herself onto me, also driving my hips up into her. The air was filled with slapping wet flesh and our moans of passion. On some unspoken signal, both of us leaned back into the chair, our pace was less frantic but just as passionate. Penny stroked herself up and down my cock, and leaned back her head so that we could make out. One of my hands reached up to pinch and pull her nipple while the other went down to play with her clit. Penny’s hands also got into the action – her unattended breast soon had one of her hands mauling it and her other hand was on top of mine on her clit, pushing me to pleasure her more. It wasn’t long before Penny’s thrusts and strokes were becoming disjointed and lost their rhythm. Her breath became ragged and she couldn’t keep her concentration enough to maintain a kiss. I rubbed her clit all the harder while driving my hips into her as much as possible. Penny let go of a long moan and her body shuttered, out of control as her orgasm overtook her. It was a good long one for her and I let her ride it out for as long as possible. Eventually it came to an end and she leaned back against me, spent.
I let her rest a moment and then gently thrusted my hips up, letting her know that I was not finished yet. “A good little secretary can’t leave her boss like this – he needs to be cleaned up and presentable to clients” I whispered into her ear. With great effort Penny leveraged herself off of me, my cock slipping from her pussy with a trail of goo connecting the two of us until it finally broke. She turned around and just before she went to kneel before me, I told her to go get the camera. She took the few steps to grab it and brought it to me. As she gave it to me I told her “good girl”. As Penny kneeled at my feet I brought my butt to the edge of the chair to make things easier for her and I also got Penny and my cock in frame. She started by licking and kissing all around the base of my cock and my balls – she was getting them clean – just as I had asked. Next up was the shaft which got largely the same treatment – not that I was complaining – it was grade A treatment! Finally Penny reached the head with which she started with more of what she was doing, but soon she was bobbing her head up and down on it. During this time I had not been still – instead of keeping the camera dead on I had switched it back and forth between that and more of a side view. In some ways I wished I also had a more distant view to see all of Penny as she gave me a blowjob – but you can’t have everything in life. Soon though I had it back dead on her and I let her know that I was soon going to finish. Our 3 outfit night and today must of really of changed her mind or rewired it or something because instead of immediately coming off my cock like I expected, she speed up and her tongue became more involved. Eventually, the site of my wife sucking my cock, covered in her juices, after all of the fun we had just had, was too much, I warned her quickly once more and then exploded into her mouth. Penny did very well, she barely gagged and only a little bit of cum got out of her mouth. After making sure that I had squirted my last, Penny kept her mouth as a seal and backed off my cock, making sure that it came out clean. She leaned back onto her heels with a thoughtful look on her face – it was only her second taste of cum and this time she had a much greater sample size. I zoomed the camera up onto her face and directed her “Open your mouth, let me see my cum in there”. Penny complied and played with the cum with her tongue. After a few seconds I gave a second direction “Swallow it”. Mouth closed and a large gulp later, it was gone – Penny reopened her mouth to prove that it was gone. Falling backwards, I muttered “good girl”. With a smile, Penny leaned forward, kissed my cock and got up. She gathered up her clothing and started to walk towards the stairs. “I hope I performed as you wished today. I do like being a good secretary” she said over her shoulder. Fortunately I had the presence of mind to continue filming until she had walked up the stairs and out of sight.
Source: reddit.com/r/sexystories/comments/8on050/sexretary_penny_and_i_2_mfroleplayfilmed