Monday Mornings, Part 1
Monday mornings always sucked. This morning was worse than usual however. My head still hurt from imbibing way too much alcohol over the weekend. I hadn't drunk so much that I blacked out since I was a 19 year old corporal and stationed at Fort Hood, Texas; over a decade ago. I guess it just goes to show that sometimes a guy never learns.
I tried to ignore my lingering headache and focus my attention at the task at hand. Following my usual morning routine, I was making the final adjustments to the large butt plug that would work Mandy's veteran asshole for the rest of the day. Mandy was my personal secretary. She was a cute, mousy, little blond in her early 30's. You know the type: Bubbly personality. Terminally flirty. Every guy at the office's wet dream. I'd been plugging up her ass for years, ever since we discovered our mutual love of the gaping female nether hole over a few too many beers at the bank's Christmas party some time back.
"Mr. X, would you mind finishing up? I need to get the Franklin account filed before lunch," Mandy asked politely as my mind wandered again. She was bent over my desk with the skirt of her suit thrown up over her back while she reached around to pull her ass cheeks apart helpfully for me. I had the three inch by twelve inch rubber dong about half way up her bum when I had gotten distracted with thoughts of my old military days.
I didn't approve of normal butt plugs. In my very learned opinion, the tapering at the neck allowed the sphincter to relax and defeated the entire purpose of the exercise. As such, I preferred dilator plugs that either were a consistent thickness along the entire length or even got wider towards the base. Of course this required rubber or leather panties to be worn to keep the plugs in, but that was a mute point; she had to wear panties anyway, didn't she?
"Sorry Mandy, here you go," I apologized as I forced the remainder of the plug into her bottom. I massaged her well toned ass cheeks as she gasped in surprise and tensed at the unexpected violation. "I trust this is to your satisfaction?" I asked as I pulled up her leather panties, situated them around her waist and attached the tiny padlock at the small of her back, locking the plug in her ass until I took it back out just before we left for the day. The lock was unnecessary as she would never take it out without asking, but we both enjoyed out little games together and the added aspect of submission really got her juices flowing. Sometimes I was a little jealous of her boyfriend Jeff as she was usually so hot and bothered by the time she got off work that he was the one who got thrown onto the bed and fucked when she got home, not the other way around.
"That's just about right. Thank you Mr. X," Mandy said as she stood up and smoothed out her pin striped skirt over her bubble butt. She would be moving around the office all day with that large plug shoved up her backside while most of our coworkers would be oblivious to the plight of her straining sphincter and well stretched lower intestine. "Although, over the last week or so, I've really started to be able to get around without much discomfort. In fact, I almost forget I have this in me sometimes. I think we may need to step my butt up a size or two tomorrow," she said mischievously and grinned.
"I think that's a lovely idea, Mandy!" I responded. "Why don't you take the petty cash credit card down to the boutique over lunch and buy a few more appropriately sized models and we'll try them on for size tomorrow morning. Just to make sure we have enough time for a proper fitting, clear my schedule from 8:00 to 9:00 tomorrow morning. That should give us enough time to properly pack your hole. I'm thinking something around three and a half inches wide and maybe sixteen inches or so long. Use that as a baseline but get whatever size you think will make you feel most uncomfortable but still allow you to get you job done."
"Of course, Mr. X. That sounds perfect," she responded as she headed for the door, ass swaying provocatively as she did. "Oh! Don't forget, you have a 10:00 AM with Mr. Bixby from City Mutual and an 11:00 AM lunch meeting with Mr. Stevens from corporate." With that she was out of my office and back to her duties.
Damn! I hate it when she leaves but I love watching her go!
***
I tried to ignore my lingering headache and focus my attention at the task at hand. Following my usual morning routine, I was making the final adjustments to the large butt plug that would work Mandy's veteran asshole for the rest of the day. Mandy was my personal secretary. She was a cute, mousy, little blond in her early 30's. You know the type: Bubbly personality. Terminally flirty. Every guy at the office's wet dream. I'd been plugging up her ass for years, ever since we discovered our mutual love of the gaping female nether hole over a few too many beers at the bank's Christmas party some time back.
"Mr. X, would you mind finishing up? I need to get the Franklin account filed before lunch," Mandy asked politely as my mind wandered again. She was bent over my desk with the skirt of her suit thrown up over her back while she reached around to pull her ass cheeks apart helpfully for me. I had the three inch by twelve inch rubber dong about half way up her bum when I had gotten distracted with thoughts of my old military days.
I didn't approve of normal butt plugs. In my very learned opinion, the tapering at the neck allowed the sphincter to relax and defeated the entire purpose of the exercise. As such, I preferred dilator plugs that either were a consistent thickness along the entire length or even got wider towards the base. Of course this required rubber or leather panties to be worn to keep the plugs in, but that was a mute point; she had to wear panties anyway, didn't she?
"Sorry Mandy, here you go," I apologized as I forced the remainder of the plug into her bottom. I massaged her well toned ass cheeks as she gasped in surprise and tensed at the unexpected violation. "I trust this is to your satisfaction?" I asked as I pulled up her leather panties, situated them around her waist and attached the tiny padlock at the small of her back, locking the plug in her ass until I took it back out just before we left for the day. The lock was unnecessary as she would never take it out without asking, but we both enjoyed out little games together and the added aspect of submission really got her juices flowing. Sometimes I was a little jealous of her boyfriend Jeff as she was usually so hot and bothered by the time she got off work that he was the one who got thrown onto the bed and fucked when she got home, not the other way around.
"That's just about right. Thank you Mr. X," Mandy said as she stood up and smoothed out her pin striped skirt over her bubble butt. She would be moving around the office all day with that large plug shoved up her backside while most of our coworkers would be oblivious to the plight of her straining sphincter and well stretched lower intestine. "Although, over the last week or so, I've really started to be able to get around without much discomfort. In fact, I almost forget I have this in me sometimes. I think we may need to step my butt up a size or two tomorrow," she said mischievously and grinned.
"I think that's a lovely idea, Mandy!" I responded. "Why don't you take the petty cash credit card down to the boutique over lunch and buy a few more appropriately sized models and we'll try them on for size tomorrow morning. Just to make sure we have enough time for a proper fitting, clear my schedule from 8:00 to 9:00 tomorrow morning. That should give us enough time to properly pack your hole. I'm thinking something around three and a half inches wide and maybe sixteen inches or so long. Use that as a baseline but get whatever size you think will make you feel most uncomfortable but still allow you to get you job done."
"Of course, Mr. X. That sounds perfect," she responded as she headed for the door, ass swaying provocatively as she did. "Oh! Don't forget, you have a 10:00 AM with Mr. Bixby from City Mutual and an 11:00 AM lunch meeting with Mr. Stevens from corporate." With that she was out of my office and back to her duties.
Damn! I hate it when she leaves but I love watching her go!
***
3 years ago
