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 konyaaltı kendi evi olan escort 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 konyaaltı otele gelen escort 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 konyaaltı rus escort 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.