Intern's First Business Trip


"No. NO!" I yanked my hands away. My cock forced itself against the front of my pants. "I ... uh ... I ..."

"Oh my goodness! Are you really this innocent? Settle down; settle down. Look at you shaking." She grabbed her towel and hooped it back over her head. The ends nestled back onto her breasts for whatever good that did. "Relax, Timothy. I'm just having a little fun with you. Now get undressed."

"Ma'am?! Oh, the laundry. Yes, ma'am," I replied and cleared my throat. I turned to leave the room.

"Where are you going?"

"To the bathroom."


"Well, I didn't want to change in front of you."

"Oh for heaven's sake, Timothy, the maid will be here any second. Just start stripping, and I'll bag your clothes for you."

"But I ..."

"Timothy," she snarled. "Let's go. I want to get back to the presentation."

I relented. I pulled up on my sweater. Then, as I fumbled nervously with it over my head, I felt my boss taking off my shoes. Pulling my head through the neck hole, I looked down to see her on her knees in front of me, sliding the socks off my feet. Then she reached up and undid my belt. My hard-on strained as if wanting to burst out and meet her.

"Oh, ... um ... would you like me to ... maybe I should do that, ma'am," I stammered.

Looking whimsically up at me through the tops of her eyes, she yanked the zipper down its length. Then she slid her hands inside my fly to my hips and loosened my slacks to slip down to the floor. Directly in front of her eyes, my erection pressed shamelessly into the front of my briefs.

As I fiddled furiously with my shirt buttons, Ms Strickland stared directly at my bulge. I was afraid what she would conclude from my condition, and as if to confirm my fear, she began to nod her head. "I knew it," she said.

"Knew wh-wh-what, ma'am?"

"White jockeys. I knew you were a tightie-whitie kind of guy." Just then, a knock came to the door.

*** Bathroom ***

As my boss went to answer the door, I escaped to the sanctuary of the bathroom. Inside, I looked down at my hard-on with disdain. How embarrassing!

Momentarily, a knock came to my door. I opened it a crack and peered out. On the other side stood a short latina girl in a baggy, utilitarian maid uniform that zipped up the front. She appeared to have long brown hair, but she had it clipped into a bun at the back. Her cherubic face made her look younger than she probably was, and her strong Mayan nose made her look a little plain. But then she smiled, and suddenly her face filled with her grin and teeth and cheek dimples. It was pleasantly unsettling.

"Perdón, señor, I come for clothes."

"Yes, the woman has them outside." I closed the door and looked around the bathroom for something to wrap over my briefs. Clearly, I wasn't going to be able to trust my penis to behave for the rest of the night. Unfortunately, my boss had used all of the large towels.

The maid knocked again and then slipped into the room, closing the door behind her. "Perdón, señor, I mean those clothes. Señora say I must take underpants." Before I could object, she crossed the room and kneeled in front of me. She grabbed onto the waistband and yanked. By reflex, I cupped my hands over my groin, but it afforded me little grip on the briefs.

"Wait, wait, wait! I'm not sure that I need ..."

"Por favor, señor, I must take." She pulled steadily and slid the briefs slowly down my legs. The elastic waistband dragged roughly down the underside of my cock, sending a thrill into my groin. I made one last grab for them, but my release allowed her to pull them down completely.

My erection waggled freely out in front of me, and grinning widely, she flicked the end of it with her finger. "Ay, Papi, qué miembrillo!" She cupped her hand over my erection and gave it a little rub. "Es grande, no?"

A warm buzz went down my shaft and into my balls. I couldn't believe it. No woman had ever touched my naked penis before. I tried to cover myself, but her hand was in the way. "Ohhh," I shuddered.

"Mmmm, you like I help you?" She wrapped her hand around my hard-on and pulled it out from my body. Then she leaned her mouth towards the tip, almost touching it, and looked up at me through the tops of her eyes. "Mamo su pene?"

"No," I said weakly. "You have to stop."

She pouted, and as her lower lip extended, it grazed the tip slightly. "Okay. I stop." She then gave it a tender nibble, which made me jerk in her hand. She giggled and stood up. "When Mamacita leave, you call for Maria, okay?" She gave me a peck on the cheek and turned to go, my briefs in hand.

"Wait! Do you have any towels? I need to cover myself."

She turned back around. "Qué?"

I mimed a towel wrapping around my waist. "A towel?"

"Ah, si, una toalla." She grabbed a small facecloth off the towel rack and laid it gently over top of my erection, as if she were moving it from one towel bar to another. It drooped lightly over my pole, providing almost no cover. "Adiós, Papi." She gave me another peck on the cheek, giggled and breezed out.

Through the open door, my boss stared in shock at my tiny loincloth. I quickly shut the door and desperately looked around the bathroom for a better covering. Ms Strickland knocked on the door. "Timothy, come out. Don't be shy."

"Yes, ma'am. I'll be out in a second." I could only find a hand towel and tried wrapping it around my waist. With it, I could either cover my front or back but not both. I chose the front and pinned the towel on my hips with my hands. My erection pushed out on the loose material, as if trying to escape under the bottom hem. I wrestled with the doorknob, trying not to drop the towel in the process, and stepped outside.

Ms Strickland pouted. "Oh, I liked the other towel better."

I blushed and sidled away from the door, keeping my backside pointed away from her. As I passed, her eyes remained fixed on my projection. She bit her lower lip. "So what were you doing in there so long with the maid?" She placed a fingertip on the end of my hard-on and twanged it.

I shuddered and stepped back. "Nothing, ma'am. I ... she ... We couldn't find a towel for me to cover myself."

"Uh huh," she murmured sceptically. "You know, you don't have to cover yourself if you don't want to." She hooked a fingertip into the towel at my waist and plucked at it.

I lurched back. "Oh ... uh ... I ... uh ... I think I would prefer to, ma'am."

"Hmmm. Well, go get the presentation ready. I'm just going to get changed."

"Okay," I said, backing towards the desk. "Oh and ma'am, could you bring me one of your towels when you come out?"

"Sure, Timothy, if you're finished teasing me, I suppose I could." She didn't really think I was teasing her, did she?

She walked over to her luggage and rummaged through it. She kept holding up flimsy pieces of clothing and pondering. I started to picture her in each one that she considered, but it got me really hard, so I settled myself down at the desk and turned my attention back to the presentation. Finally, she breezed past me, letting her final selection skim over my head in passing, and disappeared into the bathroom.

*** Desk ***

I shifted my bare cheeks on the itchy material of the chair and re-arranged the towel over my lap. My erection pointed wilfully up underneath. I tried forcing it to lie against my stomach by pulling on the towel and tucking it under my ass, but the ends of the towel kept spitting out whenever I budged. So I just hunched over my lap to hide it and looked back at the screen. Maybe if I concentrated on my work, the erection would go down on its own.

Soon, my boss returned, wearing a mauve nightie that shimmied uncontrollably as she approached. When she drew up next to me, I could see why. Through the thin material, I observed that she had nothing on underneath. Her aureoles and pubic hair made dark purple outlines on the mauve cloth. I swallowed and looked away. I could feel my heart rate increase.

"Here's your towel," she said and placed something light on top of my head.

I reached up only to find a facecloth. "No ma'am, I meant one of the bath towels that you had."

"Oh, did you? But I liked this one," she purred. "Anyways, the bath towels are wet. I used them to dry myself." She put a finger under my chin and rotated my face towards hers. "And to wipe myself. Is that what you wanted?"

I blushed. "No ma'am. I'm sorry. I wasn't thinking." She had an unsettling grin on her face. "Ummm, I have the presentation up."

"Yes, I see." She stepped between me and the desk. I had to spread my legs to give her room.

"Oh, would you like to sit down here?" I grabbed the chair's armrests to stand up.

"No, no, no. You stay where you are. This'll only take a minute." She bent forward, thrusting her bum into my face and causing me to flop back in the chair. The flimsy material drifted up the back of her legs and crested her soft, round cheeks. The dark separation between her fleshy mounds peeked under the nightie's hem. I turned my head away but found myself constantly glancing back. I chastised myself for being so weak.

"Which slide has the sales projections?" she asked, opening her legs slightly. Between her thighs, a tuft of dark hair appeared as a feathery silhouette. My pulse began to pound, and my penis throbbed in sync.

"Umm ... ohh ... fifteen, ma'am." I swivelled my head towards the bed and tried to find an object with which I could distract myself. Instead, I caught my boss's reflection in the glass of a painting. Her breasts drooped heavily in the thin nightie, and her ass pointed directed at my face, as if being offered. I found the image embarrassingly stimulating and had to shut my eyes.

"Did you use last year's sales figures or this year's?" she asked.

"This year's, ma'am."

"Good, but the title is wrong."

I didn't realize she was sitting down until I felt her ass settle onto my balls. Then she slid up towards my stomach. The rough terrycloth rasped up the underside of my hard-on as she went. I felt a twinge in my balls as if something were about to happen. The friction felt wonderful and exciting, and I lurched in my seat at the surprise of it all.

Ms Strickland turned on my lap. "Oh sorry, did I sit on something."

"No, I ... uh ..." I coughed. "I just ... uh ... didn't expect it." I cleared my throat.

"You're okay?"

"Umm ... yes, ma'am."

"Good." She turned back to the computer, and in doing so, she lifted off my lap and repeated her backward slide. Again, the friction caused my groin to twinge and grip. My penis went completely rigid. I clutched onto the chair's armrests, but nothing happened.

"Oh dear, I've done something."


"I've lost the data or something." She sat back and let me view the screen.

I leaned forward. At the corner of my eye, I could see her full breasts pushing on the thin nightie. "Oh, I think you just wrote over the link. I can fix that."

I grabbed the mouse and was surprised that she didn't get up to let me at the laptop. Instead, she put an arm around my back and balanced on my thigh. I tried to concentrate on the repair, but I kept noticing her breasts inching towards my face. I made some clicks on the screen and then felt silky material on my cheek. I clicked furiously through the file directory, while one of her fleshy mounds mushed into the side of my face. I could feel her hard nipple poke into the skin of my cheek.

I found the correct table of data and re-linked it. The compressed nipple slid towards my mouth. I fiddled with the axes and tried to move my head away, but the breast stayed firmly against my face. The nipple got closer and closer to my lips. Finally, I got the chart back to its original state and flopped back in the chair. "There. That should do it," I announced with relief.

Ms Strickland hovered over my slumped body with a glint in her eyes. "Good boy, Timothy. Then it's bedtime. Let's call it a night." She jumped off my lap and hustled to the bed.

*** Bed – Night ***

Ms Strickland turned off the lights and slid between the bed's crisp sheets. I saved the file and shut down the computer. I didn't know where I was going to sleep though. I had thought that I would try the chair and rest either my feet or head on the desk, but now that I was there, I realized how uncomfortable that would be. No, it had to be the floor, I guess.

I held the towel at my waist and stood up. With my erection at full strength now, I had to bend over to make it less prominent. I shuffled over beside the bed and lowered myself slowly onto the floor, being careful not to let the towel fall. My boss watched my balancing act with an amused grin.

I fidgeted around on my back to make the best of the hard surface and then arranged the towel on my lap for best coverage. I was far from comfortable, but I figured that I would probably drift off at some point during the night.

Propped sideways on her elbow, Ms Strickland leaned over the side of the bed. "Comfy?"

"I'll be all right, ma'am," I said stoically.

"Will you?"

"Yes, ma'am, don't worry about me?"

"Want anything?"

"Um ... could I borrow one of the pillows?"

"One of these?" She held one up in the air.

"Yes please, ma'am."

She returned it to the head of the bed. "No, I'm sorry, Timothy, but I'm going to need all these pillows for myself."

"Oh, okay. That's fine. I'll be okay."

She broke out laughing. "Oh, for heaven's sake, get up here."


"Timothy, I'm not going to let you sleep on the floor. Get into bed. My goodness, I'm beginning to think that you're hopeless."

Well, I hadn't expected that. I got off the ground and slipped carefully under the covers. The bed was not very large, and I made every effort not to touch my boss's body as I climbed in. Under the sheets, I arranged the towel over my lap and braced myself into a rigid position to ensure that I wouldn't roll into her during the night.

Ms Strickland watched me get settled. "Finished?" she asked.

"Yes, ma'am."

Suddenly, she reached under and whipped my towel away, tossing it onto the floor. I swallowed but didn't move. "Relax, Timothy," she said, placing her hand softly on my shoulder.

"I am relaxed, ma'am."

"No, you're not. You're like a plank of wood." She snaked her lower arm under my neck and snuggled her body into my side. I gasped. I could feel the silky material of her nightie along my arm and the warmth of her breath in my ear. She slid her other hand under the sheets and petted my chest gently with her fingertips, as if she were soothing a frightened puppy.

"Should we be doing this, ma'am?"

She continued to pet me. Her caresses were light and ticklish. "Why? What do you think we're doing, Timothy?" She stroked my upper chest and then let her hand slip lower.

"Sleeping so close together in the same bed, I mean." She stroked lower on my chest a couple times and then let her hand drop again.

"Shhh. It's a small bed, Timothy. Go to sleep." She stoked my stomach and then moved lower. I grew anxious.

She moved her hand to my abdomen and accidentally touched the base of my penis. I inhaled audibly. She forked her fingers around either side of the base and dragged her nails back through the pubic hair, making it crinkle as she combed.

"You're not sleepy, are you?" she breathed into my ear.

"No, ma'am," I tried to say but ended up whispering.

She ran her hand down the top of one of my thighs and scraped her fingernails up my inseam on her return. "I think I know what the problem is."


She carefully peeled off our coverings until there was only one sheet over our bodies. My erection propped it up at my waist. "I think I know what's wrong," she said, playfully shimming the sheet in against the prop. With each adjustment, the sheet took on more and more the shape of my cock. "I think ..." She shimmed. "I see exactly ..." She shimmed. "why you're ..." She shimmed. "not tired." Finally, the sheet wrapped around my upright pole.

Ms Strickland grasped the white cotton column around the base. "You're just a little overexcited. That's all." She moved the sheath slowly up and down, sliding the cloth over my sensitive skin. It felt glorious, and I let out a sigh.

Up and down, she pumped. Up and down. "So what do you think we should do about it?"

"Ma'am? ... Ohhh ..."

Up and down. Up and down. "Well, what does your girlfriend do for you when you get like this?"

"I ... uh ... I don't have a girlfriend ... Ohhh ..."

Up and down. Up and down. "Okay, well when you've had a girl help you out, what did she do?"

"I never ... Mmmm ... I never ... Mmmm ... with a girl ... Ohhh ..."

Ms Strickland stopped and leaned over my face. "Never?"

I shook my head.

She reclined and stared at the ceiling. "Well, that explains a lot." Then she propped herself back up. Now she had a weird look in her eyes. She slid her arm underneath the sheet, and I braced myself. "I don't think I've ever been in bed with a virgin before."

I felt embarrassed. "Sorry, ma'am."

She closed her eyes. "Oh gawd, don't be sorry." I could feel the bed vibrating but nothing else. I looked over to see her moving her arm up and down, but I couldn't feel her touching me. She seemed to be rubbing herself under the sheet. With her eyes closed, she said, "Timothy, I want you to say, 'I'm a virgin'."

The bed shimmied beneath me. "I'm a virgin."

"Mmmm, say it again."

The bed pulsated even more. "I'm a virgin."

"Ohhh! Now say, 'I want you to take my ...' Wait!" She stopped abruptly and sat up. "Don't move." She jumped out of bed and picked up the phone. I shifted to get more comfortable and accidentally moved my hand over where she had been lying. The sheets were wet there. She must have been sweating.

"Doreen?" my boss said into the phone. "I didn't wake you, did I? ... Sorry about that. I just phoned to follow up on our conversation. ... I see. Yes, well you did seem a little reluctant in the elevator. ... I understand. No, that's fine. Oh, by the way, I think I forgot to mention something to you. Did I tell you that the presentation I brought this year has never been given to anyone before?"

I could have told her that. I only prepared it the day before we left.

"No, Doreen, you're not getting it. I mean EVER. ... That's right, not to anyone. ... That's it. ... That's right. ... I thought you would appreciate that. ... Okay, when? ... Yes, yes. And the LOI? ... Well, persistence does pay sometimes. ... No, I absolutely guarantee it. ... Oh, don't worry." Ms Strickland looked over at me. "You'll know. You'll certainly know. ... Okay, then. Good night."

Boy, there was a lot to doing business that I had to learn yet.

Ms Strickland hung up the phone and raised her arms in victory. "Yes-s-s! Let's see her get to sleep now." She danced over to the bed and leaped on top, landing on her knees beside me. She leaned over my face, her breast wobbling under her nightie. "Timothy, you and your cornball morality are going to pay off big time for us. I knew that I sensed something about you in the gym."

I wanted to ask her what had just happened, but she suddenly lunged at my face and gave me a big kiss on the lips and then another and then another. I felt both shocked and excited. Then she slipped under the sheets and cuddled up to my body.

"Timothy, tomorrow I need you to take your time giving the presentation. If you finish too soon, it will not be a good thing."

"I understand, ma'am."

"Actually, you don't, and that's what's so great." She gave me another kiss on the mouth and then got a weird look in her eye. "You know, we can't practise tonight, but I sure can warm you up."

"Really?" I sat up. "Do you want met to turn the laptop back on?"

"No," she said, pushing me down. "I want you to lie back and relax."

I was totally confused. As she ducked her head under the sheet, I stared down at the resulting lump and decided to ask her what ... Yikes! All of a sudden, her hand wrapped around my penis. She stroked it gently up and down. I inhaled sharply.

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