10 comments/ 81944 views/ 41 favorites Jenny The Intern Takes Control By: writemarksmith I'd like you to meet Jenny, our new intern" James said with goofy smile. The small ad agency I ran hired an intern every summer, and I could see why there was a buzz around this one. Jenny was a twenty-one year old who exuded sexuality. She was sitting at her new desk, wearing a fitted white skirt that showed plenty of her crossed legs, a red summer sweater with a V-neck that plunged just enough to show a hint of her pert young breasts, and open toed shoes that exposed a fresh, bright red pedicure. Jenny had dark hair, smooth white skin, big pillowy lips, and gorgeous brown eyes that had a knowing look. "Very happy to meet you Jenny." I said with a kind but authoritative voice. "Mmm...I'm sure you are" she said with a giggle and a smirk. My throat caught, unsure how to respond to her playful insolence. I looked at James and he seemed not to have heard her at all, just smiling and staring at Jenny's tits. I decided to let it slide. "Yes, well...welcome" I walked away thinking about how easy it would be to get lost in her eyes. I had been married for 15 years, and had been mostly faithful, although there had been a couple of employees I had bent over the desk at my last agency. In the three years I had become Managing Director at this agency though, I had been much more careful. I shook the thoughts out of my head and got to work. Jenny's cubicle was not far from my office, so I saw her a few times that first morning. Each time I felt a curious tingle go through my body after which I would scurry off, nervous someone might see me staring. When she caught me looking one time, she gave me a little wave and to my disgust, I felt my hand go up and give her a fey wave back. That afternoon when I went to get a coffee from the machine, I passed Jenny's cubicle and felt a pang of disappointment when she wasn't there. Suddenly I saw her in front of me, getting herself a tea. She smiled sweetly as I struggled not to look at her ass and fumbled with the coffee pot. My voice cracked slightly as I asked, "So Jenny, how has your first day getting..." "I love a hot cup of afternoon tea," she interrupted breezily, "I mix the green with peach, it's so good." I started to form a response, but she touched my arm as if to dismiss me and walked away. I couldn't resist watching her ass sway in her white skirt as she sauntered down the hall. That night I couldn't get this beautiful young girl out of my mind. I jacked off twice, and both times my fantasy didn't get past her slipping out of her work clothes and exposing what I imagined must be a perfect, tight body. The next day Jenny was with a large group in a conference room all morning, meeting with a few people from one of our clients. Charming clients is an important part of my role, so at lunch I joined the meeting, and as I tend to do, started to tell an amusing story. I had the attention of all in the room as I told my animated tale, moving my gaze from one guest to another. When my eyes caught Jen's big eyes looking back at me, however, my throat caught and I stumbled, losing my flow. Jenny was not dressed as overtly sexy as the day before, but still looked hot in a tight white blouse, a black pencil skirt and black suspenders. She seemed to look right through me and read my dirty thoughts. I managed to get it together and finish my story, then quickly excused myself, went directly to a stall in the bathroom and jacked off again. There was something magical about this girl, but I chastised myself, worrying that I may not get any work done all summer if I couldn't get her off my mind. Around 3pm, when I went to get my coffee she was back in her cube. I challenged myself not to stare at her while I passed, but heard her sweet voice ask me "oh, could you get me a tea while you're there Rick?" "Yes...I...sure, of course." I was trying to send casual and cool, but somehow I knew it came out as anxious. I carefully took a bag of green and a bag of peach and dipped them into the hot water. I carried it back to her thinking we might chat a little, but Val, a cute Vietnamese girl from Accounting, was in her cube telling her something. When I went to hand her the tea jenny stayed focused on what Val was saying but motioned for me to place the tea on her desk. She nodded when I did so, but continued talking to Val. I waited a moment and when I realized I was just standing there listening to the two young girls gossip, I awkwardly left and walked back to my office. As I rounded the corner, I heard the two of them giggling loudly and wondered if they were laughing at me. As I walked from my car to the office on Jenny's third day I reminded myself that I couldn't have others see how smitten I was by this girl, half my age. When the elevator doors opened to our office, Jenny was the first thing I saw, casually bent the receptionist's high desk, chatting with her. Jenny wore a beige mini skirt that both exposed her legs and wrapped tightly around her perfect, round ass. Both girls both looked up at me and smiled as they said good morning, and I simply nodded and walked quickly to my office. I realized I hadn't even responded, but was pleased with how disinterested I must have seemed. Safely in my office, I took a few calls, made an important decision at a meeting and started to feel in control again. When I left for a business lunch with a potential new client, I didn't even have Jenny on my mind, but as I went to get the elevator I saw Jenny there with Nina, also heading down for their lunch break. I took Jenny in again as I smiled at the two of them. She looked too almost too sexy for work with a tight purple blouse that didn't show that much cleavage, but with three buttons undone there was a lot of promise. Val seemed to be dressed for the gym. The three of us got in, and as the elevator started down Jenny said to Val, "turn around and show him." Val's eyes widened but Jenny reached over and physically turned the petite girl around. "Now Rick, tell Val that this is not appropriate for the office" she stifled a laugh as she pointed at Val's ass, wrapped so tight in white yoga pants that you could imagine she was wearing nothing at all to cover her pert little bottom. Val had less curves than Jenny, but had a nice tight body that she clearly took great care of. "I...well...she..." I started, not wanting to make Val feel uncomfortable as I felt my cock hardening in my dress pants. Val turned herself around showing her reddening cheeks "It's fine...I have a class, and of course I'll change back after." Jenny giggled as Val playfully pushed her, then she slowly looked down at the bulge in my dress pants. "Well, enjoy your lunch Rick" she said with a smirk and walked out of the elevator as the doors opened. I heard the two of them giggling as they walked out and I stood there trying to compose myself. I remained distracted throughout my lunch. When I came back told my secretary to cancel my afternoon meetings so I could get some work done. I wanted to go and jack off again but instead shut my door and pushed myself to focus. Around 3pm I was dragging and really felt like I needed my afternoon pick-me up. I got up to get a coffee, then quickly sat down when I realized that I didn't want to pass Jenny on my way. At 3:15 I received an email that read simply; Rick, when you get your coffee could you fetch me a tea as well? Jenny I read it five times, my throat now dry. How could she think I would...was she just joking? I looked again at the verb she had chosen; 'fetch'. Could that have been an accident? I really needed that coffee to clear my mind. I got up, unsure how to handle Jenny's request. I noticed my hands shaking slightly as I opened my door, and tried to puff myself up a little as I broke into a stride towards the coffee machine. Jenny was in her office as I passed, but I kept walking and deliberately averted my eyes. When I got the machine, Bob, my CFO, was there and we chatted about the monthly close while I got myself my coffee. When he left, I looked at the tea selection, paused and then found myself carefully selecting a green tea and a peach, and pouring boiling water into a cup for Jenny. I walked to her office and tried to put on a confident smile as I brought her tea. She smiled sweetly up at me and said "Ohhh...you're such a sweetie, thanks!" I felt a sort of pride in pleasing her like this and she started to talk to me at length for the first time, telling me something about her first days and what she had learned. I tried to listen but couldn't help being distracted by how much of her long smooth legs she was exposing as she crossed her legs in her seat. Then I saw that she was playing with her high heels shoe, dangling it precariously from her toe. She was telling me something about how much she had learned about social media when her shoe dropped to the floor near my feet. She made no motion to get it, instead simply looked up at me with her big doe eyes, her bare foot now pointed towards me. Somehow, I knew I shouldn't do it, but I bent down to pick up the shoe for her and found her painted toes inches from my face. I knew as I did this, it would be strange to hand her the shoe so I half-assedly placed it on her bare foot and stood up. "Good" she said, simply as if this was completely natural. I knew my cock was again hard enough to show through so I mumbled something and quickly turned around and reverted to my office. I didn't leave until after 6 when I hoped everyone had gone home and I had to piss too badly to stay in. Jenny The Intern Takes Control Ch. 02 Jenny's fourth day was a training day offsite. I felt like my old self again, challenging my team to do better work on a new campaign, and even closing a new client who had been delaying making a decision for several months. Of course, I did think of Jenny...especially her smooth white legs and her sexy smirk, but I was able to shake it off, even laugh as I told myself that I surely could handle an intern half my age. The one small challenge I had was at the end of the day when I had a meeting with Bob and Val. It was all business, and Val was dressed quite conservatively, but as Bob went on about the need to keep travel expenses down for the quarter, Val took her bare foot out of one shoe and started to stretch her toes. I noticed how tiny Val's feet were and the french manicure that carefully framed each toe. Suddenly I looked up at her and realized she had seen me staring at her toes and I jerked my head back up, heart beating fast. Did she know what happened yesterday with Jenny? Her face gave no sign, but I quickly ended the meeting. God, this new intern was really playing tricks with my head. Friday was casual day and when I saw Jenny, I realized she had taken full advantage, wearing a simple sundress, minimal make-up and a pair of flip-flops. She looked even younger than her years and fresh as could be. My calendar was jammed all morning and I had booked the afternoon to finish preparing for Monday's board meeting. When I reviewed what had been prepared I realized there was a lot more work to be done. Normally I would have had this all wrapped up, but I had been rather distracted all week. I started to write out changes and additions and gave them to my secretary to prepare for the presentation. At 6pm, she told me she had to leave to pick up her son, but Jenny had agreed to stay and get any further changes on to PowerPoint. I wondered if my secretary could see my heart start to beat out of my chest at the idea of being alone with Jenny. At about 6:45 I walked to Jenny's deck with a number of changes I needed. There didn't seem to be anyone else around, but I was still cautious as I approached. "Hi...ummm...I understand you're going to help out Jenny?" Jenny looked me up and down then at the papers. "Hmm...looks like we may be here for a while..." There was a long pause as I waited for her to continue "...tell you what, I'm hungry...if you run down and get me some pad thai, when you come back up, I might have most of these done, and...I'll even let you give me a nice foot rub." My heart started to beat even faster and I felt my face go bright red. I couldn't resist looking down at her feet and I saw that she had casually taken one foot out of her flip flop and pointed it up at me. It looked so soft and perfect I wanted to kneel down and rub it right away. "Yes, sure, I...will go right now". And I did, walking directly to the elevator, my heart beating fast. She had laughed lightly as I walked away, and at that moment I realized that I had lost any sense of decorum, any ability to deny that she could manipulate me as she pleased. It probably took me over 20 minutes to get her order, but I don't really remember any of it. I do remember going back up the elevator, hoping she would be pleased with the drink I got her and the noodles, and imagining how nice it would feel to touch her, even her feet. When I arrived back at her cube I took her noodles and soda out of the bag and carefully placed them on her desk. "Such a good boy" she teased as I hoped desperately that nobody else was in the office. "I need to get this finished up, but you can get under there and rub them if you like." She kicked off both her flip flops then turned back to her laptop. She really wanted me to get under her desk to do this? Of course, she knew I would and I did, moving some wires as I positioned myself beneath her. It was cramped, and as I placed her little foot in my hand, my face was right in front of her sole. I started to rub the best I knew how, and when she moaned softly, I felt very proud to be pleasing her. I got very hard, looking up her skirt, catching glimpses of her white panties when the angle was right. Jenny slowly pushed the foot I was rubbing forward until it was pushed against my face. As she started to wriggle her toes against my nose I felt a new wave of humiliation come over me, but I could not resist kissing her soft soles. I had lost myself in this, kissing and licking every inch of her foot, when I felt her other foot move along my leg until it was pressed against my hard cock. I sucked her toes passionately and felt my cock throbbing as she slowly stroked my cock with her foot. "Such a good bitch." she said with a giggle and I felt myself immediately cum in my pants under her desk. As I finished my spurts and breathed heavily on to her foot, I looked up at Jenny's angelic face and we both knew she would be the boss from now on. Jenny The Intern Takes Control Ch. 03 A week had passed since that Friday I had crawled under Jenny the intern's desk and worshipped her feet, but the occasion had not left my mind for a moment. Before she sent me home, Jenny had made a few rules clear that night; 1) Going forward, we would both knew I was her bitch, but she would keep this quiet from others in the office 2) I would have to agree with whatever she said in the office, no matter who was around 3) She would make all the rules, including letting me know if she ever wanted me to serve her again. Given that I was running a good sized ad agency and being paid a lot of money to do so, I should have been very concerned with #1 and #2, but it was #3 that drove me crazy. Was it possible that she would not allow me to serve her again? It seemed that every time I close my eyes I imagined her soft soles pushing into my face. Jenny did give me little treats. I got to see her at least once a day when I would fetch her a tea (I would be sure to get myself a coffee for appearances sake, but I now viewed the occasion as the time to get Jenny tea rather than my coffee break). When I brought her tea she would allow me to stand in her cubicle and chat. One time she drove me crazy by kicking off her shoes so her perfect bare feet were right in front of me, almost brushing against my leg. I knew I would have knelt down and kissed her feet right there if she had told me to, though the rationale part of me was grateful she was only teasing. A second time she taunted me less discretely. I had been delayed in fetching her tea when Frank, our IT guy started to chat me up by the coffee machine. Bob and Val walked by and joined in the conversation. I couldn't excuse myself to give Jen her tea and chat with her so I was stuck. Jen sauntered over and joined us. She was looking very sexy and confident in a white sun dress that showed a lot of bare leg. We had been talking about a high profile murder case that was in the news but Jen quickly shifted the subject. She noted that everyone needed to be punished from time to time, to keep them humble. All the men paid rapt attention in the way men often do when a beautiful girl is making a point. When Jenny further stated that she always appreciated when she was taken to task, Frank's jaw dropped, and he seemed to make no attempt to hide his lust. I was wondering if Jen really enjoyed being punished when she continued sweetly, "Even the big bosses need to be put in their place sometimes, isn't that right Richard?" I felt my face redden in front of everyone. I tripped on my tongue, unsure what to answer, but Jenny looked me right in my eyes, and without language made it clear I only had one option. "You must enjoy being put over a knee from time to time?" I felt the heat coming from my face as I stammered "Yes, well, yes I...suppose we all need..." Jenny laughed and mercifully shifted the attention away from me "and I'm sure Frank here loves a good beating!" Frank laughed loudly, Nina giggled, and Bob seemed bewildered. The group dispersed soon after that. Unable to chat with Jenny, I instead found myself in the bathroom stall, jacking off to the idea of being spanked over her lap. I thought about all of this sitting at my desk late on this Friday. How Jenny had taken over all of my dreams and fantasies...how easily she could control me. I looked up at the clock and saw it was already after 6pm. I realized I should pack up and get home to my wife, but I stared out the window and allowed myself to think of Jenny a little longer. "Dick?" I looked up and was startled to see Jenny at my door. She was dressed casually, wearing a white top with some notable cleavage, a short white jacket, and tight black leggings. Earlier in the day when I saw her walking down the hall, my heart almost stopped while I watched her ass sway back and forth. "I think everyone is gone. Stand up for me." I had no idea where this was going, but I stood immediately, wanting to please and impress her with my obedience. I noted that my office door was open and worried someone might pass by. "Oh, have you been thinking about me?" Jenny was looking at my pants and I realized I was hard from the from the day dreams I had been having of her. "I...ummm..." She giggled the sweetest giggle and told me to put my hands behind my back. Of course I did as I was told, although it had the rather obscene effect of accentuating my predicament. "Oh, I have to share this" she squealed, as she started to type something into her phone. I started to protest "What...who are you?" Jenny walked over and placed a little finger over my mouth. I tingled even at this touch and could smell her sweet perfume as she stood close. She tip toed and whispered in my ear "are you going to do just what I tell you to and trust me?" I hardened even more with the sensation of her breath and nodded dumbly. Of course I would. "Kneel." she said simply. I fell to one knee and then the other, my hands still clasped behind my back. My heart beat fast with excitement, but also with fear. Would somebody see me like this? Jenny turned and walked to the door. My face was now level with her ass and she seemed to give it an extra sway. She slowly shut the door, and walked back over. She bent down to face me, exposing a lot of her round tits. "I hope you don't mind that I invited a friend?" My mind barely had time to process this when I heard a soft knock on the door. My heart started to beat out of my chest but Jenny looked me in the eyes, and again put her finger on my mouth. She walked over, opened the door and I looked up to see Nina standing there looking at me with a big smirk on her face. Jenny let Nina in and shut the door. "Now, Nina wasn't sure she should believe that you were my little bitch," Jenny spoke in a sing-song little girl voice. "I know I said I wouldn't tell anybody but...well they are my rules so I thought I could break this one just a little. Jenny and Nina walked over to me, then Jen crouched down and tilted my head so I was looking up at Nina towering over me. "You don't mind do you?" I shook my head. I had real concerns with this development, but looking up at Nina they were fading fast. Nina looked as cute as I had ever seen her, wearing a short sleeved white blouse, with a big blue ribbon that matched the blue pleated skirt she wore. Nina was a petite Asian girl, with small tits, but the skirt showed off her perfectly smooth tan legs. The skirt must have been close to ten inches above her knee and I wondered if she had worn this outfit all day at the office. "Good boy. Get on all fours and thank Nina for coming by." I looked up at Nina who stifled a laugh as she looked down at me. I fumbled to put my hands on the floor ahead of me, and thanked Nina profusely for coming. "You can show her just how thankful by kissing her feet." Nina's blue painted toes were peaking out of her shiny black pumps. Very much wanting to make Jenny proud of how obedient I was, and almost lunged forward and kissed every one of Nina's toes on one foot, then the other. I felt a little startled to hear the two of them laughing as I finished and realized just how silly I must look down there. "Such a good boss" Nina said, speaking for the first time. "You certainly have him well trained." "He is good," Jenny acknowledged. She startled me by pushing her booted foot on my chest to get me back on my knees, then she ran her boot along the tent in my pants. "And look how excited he is to serve." Nina put her hand to her mouth and laughed. Jenny taunted "why don't you take it out for us?" I froze for a moment, unsure if I understood, but they both looked at me with knowing smirks. My hands shook a little as I undid my belt, unzipped and pulled out my hard cock, still kneeling. "Nice," Jenny said patronizingly, "just pull your pants down to your knees." I imagined how foolish I looked as I obeyed immediately, looking up at the two of them for further instructions. "Now Nina has a hot date tonight," Jenny spoke slowly and raised her boot to lightly brush my cock, "why don't you use that to polish her shoes for her?" Nina started to choke with laughter, but put one foot forward just a little for me. I crawled forward, tripping on my pants a little. I could barely believe what Jenny wanted me to do, but knew I couldn't stop now. I positioned my cock on to Nina's shoe and looked up at her. I flushed with additional embarrassment as I looked directly up her skirt. She had tiny pink panties on and I could see the bottom of her round ass cheeks. I looked down quickly and started to push my cock back and forth on her shoe. The head of my cock touched her toes with each thrust and despite my ridiculous position with these two young girls I started to worry I would cum. Nina, still laughing, took the foot away and proffered the other. I positioned myself anew and rubbed myself along her shoe, back and forth. I felt beads of sweat form on my head. "What a good job!" Nina said as if to a five year old. "Look how shiny they are." "Oh, is that a little pre-cum there?" Jen pointed with her foot, "That won't do. Lick it off." I had never tasted my own cum, and hesitated for a second, but bent forward despite myself. As I carefully licked the little pre-cum I had indeed spilt on Nina's shoe I felt completely humiliated, and for a moment wondered if this was all wrong. "Good." Jen said simply. "Now I suppose you should get a little reward for your obedience. Hmmm. Oh, before that, do you have a little cash you could give me for the weekend?" I looked up at Nina blankly, a sweaty mess on the floor, with my pants now near my ankles. I awkwardly reached back and found my wallet, and unsure of how much to give her, handed it to her. She took out most of the bills without looking and handed it back. "Perfect. Well, I know the reward you want. I saw you checking out my ass today, you weren't very subtle. People may talk if you're not careful." Jenny looked at Nina and laughed, then positioned herself with her ass inches from my face. "You love it don't you?" she teased. "You'd do anything just to kiss it. Well, here is your chance. You can stroke yourself while kissing it for just a few minutes." Jenny reached back with her thumbs and pulled her leggings down revealing a curvy white ass that was the most inviting I had ever seen. I pushed my face into an ass cheek with a kiss, then started to kiss her ass greedily, not wanting to miss an inch. I kissed the curves on the bottom, kissed her ass crack up and down as Jenny pushed her ass back gently into me. I stroked myself slowly, not wanting to cum too quickly, but when I looked to my left I saw Nina. She was sitting in a chair watching me, her face with a look of genuine amazement at the boss she had once respected desperately kissing an intern's ass in his own office. I knew I could not hold back any more and kissed deep into Jenny's ass crack, burying my face and I spurted on to the ground. Jenny pulled her pants back up, and before I knew it, the two girls both kissed me on the cheek and left me there. I was alone, half naked, still kneeling, with a mess on the carpet to clean. All I could think of was how lucky I was. Jenny The Intern Takes Control Ch. 04 I had really lost control. It had been a week after I had knelt naked in my own office and been completely humiliated by Jenny the new sexy young intern at my agency, and Nina, the petite Asian cutie who until last week I had considered rather reserved. All I could think about was when I would have a chance to serve Jenny again, but of course she had made it clear that she made all the rules. I was not allowed to ask questions, and I would just have to wait for her to determine if and when I was allowed to serve again. I did continue to bring Jenny her tea in the afternoon, as she had me do every day at the office. On Tuesday when she sent me an email reminding me to fetch her a tea she told me I would be allowed to stand in her cube and look at her feet for two minutes as a reward. She did not speak to me when I came by, she simply sat in her chair, drank her tea and looked me in the eyes while I looked down at her bare feet. On Wednesday when I brought Jenny her tea, I found Nina was in her cubicle chatting. Jen used her little finger to motion that I was to fetch Nina the same and I was off to serve her as well. I got a little hard just at the idea that I would get to chat with the two of them, but when I arrived with Nina's tea I was instead waved away by the two of them and had to walk back to my office disappointed and frustrated. Thursday afternoon started worse still. I fetched Jenny her tea, but found that she wasn't in her office. I stumbled back to my office stupidly with two teas. I passed my secretary who I think is starting to wonder about me. Late that afternoon I received an email from Jen, instructing me to wear a suit the next day and book off the afternoon. I was to be allowed to take her out for a late lunch. I cancelled my schedule for the next day, then re-read the email several times. I was very excited by the idea. I had never seen Jen outside of the office and I had no idea what she had planned for me. Would Nina also be coming? Perhaps Jenny might even allow me to rent a room and fuck her? I chose my most modern, stylish suit the next morning. I wanted to look young enough that it wasn't too outrageous that I was taking out this very young girl. I got a few catcalls in the office as it was quite unusual for me to wear a suit. I realized that when I disappeared for the afternoon, people would assume I was interviewing for another job. Shortly after I arrived at the office I got an email from Jen that told me to be at a 'Viva Italia', a nice restaurant downtown at 1pm. I was to wait for her there. The morning went by painfully slowly, but finally at 12:30 I ran out of the office. The taxi took 15 minutes so I arrived early for the reservation I made. I sat there alone, looking at my watch anxiously. I finished the scotch I had ordered to steady my nerves by, and the waitress asked me several times if I wanted to order lunch. Finally at 1:15 Jenny breezed in. She looked lovely, wearing a simple sundress that showed off her smooth legs and substantial cleavage. Every eye in the place turned to her as she walked towards my table. I stood to give her a hug but she instead stuck out her hand. As I bent forward to kiss it, she flipped it over so I awkwardly kissed the palm of her hand while a waiter came by to pull out her seat. "Hi Jenny, I'm really glad..." Jen interrupted and in no-nonsense tone told me, "It will be Miss Jen now that we're out of the office." I smiled, thinking she was joking, but she just looked back at me. "Yes...I...thank you Miss Jen." At that moment the waitress approached and I realized she may have overheard. "I'll have a glass of champagne" Jen told her. "He'll have another scotch." I smiled dumbly and looked down. Jen was crossing her legs and I admired her skin, then noticed the new red pedicure. I remembered kissing her soles while Nina had watched me in the office. "Rick you're going to want to pay attention and not mess up today, I'm giving you a special chance to be with me today." "Yes, I...thank you Miss Jen, I will." I was excited to be with her, and happy to do as she said, but I had hoped we might be a bit more relaxed in public. "Good boy." Jen said sweetly as the waitress came by with our drinks. "I have a date tonight and you can take me shopping for shoes I'll look sexy in." I tried to absorb this news, and noticed the waitress standing quietly waiting to take our order. "Let's see," Jen said, "I'll have the steak frites and he'll just have a small green salad." The waitress looked at me with a smirk, then thanked Jen and took our menus. Over the course of our lunch Jen made sure that the waitress and anyone close by could tell that i was her bitch. I finished my third scotch while picking at my salad. Jen enjoyed her steak. When Jen was finished she told the waitress to bring the check, then asked me for my wallet. I handed it to her nervously, and watched her take out cash for the lunch and leave a very generous tip. She then told me to put her shoes back on for her so we could leave. I looked down and saw that she was barefoot under the table. I looked at her a bit confused but she simply nodded assertively. My hands shook a little as I got up, then knelt down on the floor to gather her shoes and place each on her little feet. I heard the young couple beside us giggle and say something about Cinderella as they watched the spectacle. As degraded as I was it was exciting to touch Jenny's feet and see her pretty painted toenails up close. As I got back up, my face was red from the drinks and the embarrassment. It got even redder as I realized my erection was visible through my trousers. I reflectively put my hand in front of it, but realized I might be drawing even more attention. I saw that the girl at the next table was staring right at my crotch, her fork frozen in her hand. Suddenly I noticed Jen was already walking out and I scurried to catch up and open the door for her. I was glad to get out of restaurant, but as we walked out I saw Jen motion for me to keep up with her little finger and realized I may have many more tests to go. We walked down the street a couple of blocks. I followed a step behind Jen, carrying her purse and keeping my eyes fixed on her ass as she has instructed me. I knew I must look like a foolish pervert following this young beauty in my suit, but I was so anxious to please her. I followed her into a shoe store and stayed close by her while she browsed the selection. She found a pair she liked and handed the heels as me telling me to fetch a size 5. I was still trying to get the attention of an employee when she tossed me a second shoe to get. I felt the shoe salesgirl knew everything about our relationship when I asked her for Jen's size. When she returned with the shoes and offered to help Jen told her we'd be fine. Jen then sat down and pointed calmly to the floor in front of her. I was mortified to do what she was asking of me in front of everyone, but I did not consider refusing. I knelt at young Jen's pretty feet, trying not to look ahead at her cleavage just in front of me. I removed her simple shoes, then took a new pair from the box. She had chosen a strappy pair of open toed white high heels. I fumbled with the straps as I tried to get the first shoe on her foot. Jen checked her text messages while I struggled and I could feel the heat of shame burning in my cheeks even while I felt myself harden. Two teenage girls walked by and looked down at me, one of them smirking and whispering something to her friend. When I finally got the shoe buckled properly I spoke softly, hoping the woman seated beside Jen would not hear, "Miss Jen...do you like them?" Jen finished typing a message while I awaited her answer, then gave a cursory look down at her feet, "They're nice. You may buy them for me." She went back to her messages, so I started to unbuckle one shoe and carefully take it off and replace it with her old shoe, then lifted her other foot and repeated the process. Jen never acknowledged me, staying focused on her phone. I boxed her shoes and as I slunk away to pay for them I found myself keeping my head lowered. The teenaged cashier has blue tinged hair and a nose ring, and when I handed her cash I felt as though she was judging me. I returned to Jen who was still typing into her phone. I stood beside her dumbly, not wanting to disturb her. The shoe sale girl came by to tell Jen how nice the shoes were she had bought and thanked her. Jen smiled up at the girl and thanked her for the help. The salesgirl then turned away to serve another customer, bumping into me a little as she left with no apology. Jen got up and started to walk out so I followed her, carrying her purse and a shopping bag with her shoes in them. As we got to the street Jen looked at me and said sweetly, "Do you think I look nice in this dress?" I had not expected this but answered quickly, "Yes! I mean...you always...you look very sexy Jen...errr...Miss Jen." "Good. We're going to meet a couple of friends of mine from college at the Red Lion pub around the corner." With that she was walking again. I trailed behind her carrying her bags, and admiring her bottom as it swayed. I really was lucky to spend the afternoon with such a beautiful young girl I thought, even if the relationship was a little unconventional. We quickly arrived at the pub and as I walked in with her purse and shoe bag I again felt self-conscious. Jen found her two friends, Matt and Vanessa, in a booth near the back, and gave them each a hug. They looked like a fresh-faced couple from a J Crew catalogue. Matt was a little taller than I am, with broad shoulders, tousled hair, brown eyes and an easy smile. Vanessa looked a bit like Kirstin Dunst with blonde hair, sultry eyes that seemed to see inside you, and what seemed like a constant smirk. Jen sat with them and I stood, unsure if I should introduce myself. "Oh" Jen added, "this is Rick from work. He's the one I was texting you about Vanessa." Vanessa giggled and put her hand out palm down as if asking me to kiss it. I did so, clumsily and she laughed more. I shook Matt's hand who smiled and seemed genuinely welcoming and amiable. "You may sit Ricky." Jen said with a little derision in her voice. Vanessa giggled and Jen turned to her friends and started to catch up. I found a place to put Jen's bags and sat down beside her. To an passer-by our group might have looked like two couples sitting together, but if they looked closer they might notice that I was much older, much more formally dressed and that I wasn't really part of the conversation. The pub was rather quiet but no barmaid had come by for our order. Jen saw me looking for one and said pleasantly "Don't sit here waiting all afternoon. Why don't you go to the bar and fetch us some drinks?" My face reddened, but I asked Jen what she would like, then took the orders of Vanessa and Matt. As I walked to the bar I heard Jen and Vanessa laughing but I didn't dare to turn around to see if it was at me. When I asked the bartender for the drinks I could feel myself staying in the role of submissive, and I felt like he treated me as such. My head spun a little from how easy it had been for me to move from being the big boss to becoming Jenny's...Miss Jen's bitch. I came back with wine for Vanessa and Jen, scotches for Matt and I. I also brought tequila shots for everyone ('top shelf' as Jen had instructed). Matt nodded, but the girls didn't even look up from their discussion as I placed their drinks in front of them. I sat down and was about to take a drink of my scotch when Jen announced we should do the shots first. "Where's the lime and salt?" she asked me. I fumbled a response letting her know I hadn't brought any. Jen asked me why I wouldn't think she'd want us to enjoy the shots properly. "Go back and get it done right." she said. I felt bad that I had disappointed Jen in front of her friend's, and ashamed to be chastised. I got up feeling like I had my tail between my legs. "Wait!" Vanessa said. She turned to Jen, "Can I spank him for screwing it up?" Jen told Vanessa that would be fine, then told me to come over to Vanessa for my punishment. I was incredulous, but also excited. I walked around the booth to Vanessa, then turned slowly so I was facing away from her. Vanessa pushed my back, "Bend over." she giggled. I bent over a little, and could see Jen looking on from the corner of my eye. I knew Matt must also be looking and it was mortifying to think that this boy half my age was seeing me willingly humiliate myself. Vanessa let me stand half bent over like this for some time before finally cupping one ass cheek and telling me I was a good boy. She smacked each cheek, not especially hard then between giggles told me to go get the limes and salt. When I returned with everything that was required, Jen led a toast and we all drank them down. I was a little surprised when Matt licked salt off Jen's shoulder then took a lime out of her mouth. I had thought Matt was Vanessa's boyfriend but now I wasn't so sure. In fact after the drink Matt put his hand on Jen's smooth leg while I could only look on with envy. Vanessa said she would have to leave soon and playfully cautioned her friends not to fall into old patterns. Apparently Matt and Jen had hooked up a number of times in college. Jen teased that with Vanessa leaving she may not be able to resist Matt's charms on her own. The conversation carried on as thought I weren't there at all. When Vanessa got up to leave, she hugged her friends goodbye and Jen whispered something in her ear. Vanessa looked over at me with a giggle, then walked in front of me. I started to get up to hug her, but Vanessa simply pointed to the ground and told me I could kiss each foot goodbye. I looked around the bar, and even though nobody was looking I was unsure I could really go through with it. I glanced over at Jen, and could see immediately that she fully expected me to obey her friend. I closed my eyes and tried to shut out the voices in my head telling me now to do this. I had come this far and knew I couldn't embarrass Jen in front of her friends. My heart beat fast as I got on to my knees in my suit. I looked up to see Vanessa looking down at me with a big grin and wide eyes. I knew I had already shown Matt that I was pathetic, but I thought about what he must think of this new spectacle. Vanessa was wearing flip-flops and I bent forward to tentatively kiss her bright red pedicured toes. She was apparently dissatisfied because as I pulled away she lifted her toes to my mouth and I gave them another, more sincere kiss. As I went to kiss her other foot Vanessa giggled as she took her foot out of her sandal and angled it so I was presented with her sole. I kissed the bottom of her foot which was soft and salty. I felt a little dizzy as I anxiously stood back up, and damned my cock for being hard. I was now standing just before Vanessa who smirked and shook her head as she looked me in the eyes. Vanessa gave me a couple of light slaps on the cheek then walked away without a word. I looked around the bar and was amazed that there were no eyes on me. Had nobody even noticed me kissing a girl's feet in the bar? As I sat down I looked to Jen, expecting a little affirmation, but she had already turned away and was stroking Matt's hair. Unsure what to do, I sipped at my scotch, looking every bit the caricature of a third wheel. I couldn't help but look over again and watch as Matt bent in and started to aggressively make out with Jen. I looked down and saw his hand again exploring her bare leg. As I stared, Jen saw me from the corner of her eye. "Oh, are you feeling left out Ricky?." I blushed and mumbled something unintelligible, hopeful, but unsure what to say. "Awww. Matt, do you mind if I let Rick kiss my shoulder while we make out?" Matt laughed and said sure, so Jen pointed to her bare shoulder closest to me and told me I could make out with it if I remained well behaved. Matt grabbed her and started to kiss her again, and I stared at Jen's shoulder. I felt myself drawn to it, like it was pulling me in to kiss it. I kissed it tentatively at first, then started to kiss it again and again, with some tongue. I didn't have a lot of space to work with but I wanted to take advantage of what I was offered. I didn't want to see Matt, so I looked down at her shoulder and her leg. I wished it was I who was exploring the softness of her skin, but it made me hard just watching Matt do so. I noticed Jen give his cock a squeeze through his pants and felt my hard-on pushing uselessly against my dress slacks. Jen, almost seemed to read my mind when she lightly brushed her finger along my cock. Th excitement was like electricity running through my body. She moved her finger away and whispered softly in my ear, "why don't you put your hand down your pants and take care of that while I finish making out with Matt?" My mouth was open as she went back to kissing her ex. For some reason I remembered that Jen was planning a date with her boyfriend tonight. Was she going out with another guy after making out with Matt? Somehow this turned me on even more. Without even thinking it through I put my hand down my pants and started to awkwardly stroke my cock. I wasn't kissing Jen's shoulder any more, just looking at how beautiful she looked. Matt's hand was going higher and higher up her leg, exposing more of her perfect skin. I thought about Jenny's feet, how she had made me her bitch with so little effort. I quickly got to the point where I felt I would cum and didn't stop. I could feel myself spasm, then shoot into my boxers. Looking down at the stain in my pants, I knew I was never going to be allowed even a bit of dignity with Jen, but I hoped I would continue to be the boss who served at the pleasure of the office intern.