The Envelope Pt. 04

End of Part 3

I looked down and sure enough a small precum spot had appeared under my semi. I sheepishly typed back that it was indeed precum.

"Such a bad boy... Can't even get his panties on without getting them wet... You know you've had your fun for tonight, so those panties better be dry for the most part in the morning."

After a little more chatting and flirting we both agreed it was time for bed. I pulled my t-shirt off and crawled under the covers in just the silky blue panties Ginger had given me. My mind was filled with the images of the epic jack off session in the car and the on and off flirting and shenanigans Ginger had me doing throughout the day. I felt my cock inching up again as I dozed off to sleep.

Part 4

I slept good that night, which is no surprise given the absolutely mind-blowing orgasm Ginger had given me the night before. I crawled under the covers and remembered dozing off, but the next thing I remember was the alarm going off. I silenced the alarm quite surprised that I had slept all night. Normally, I wake up during the night and have to take a leak, but I had actually slept for about seven hours.

After a quick shower and shave I popped open Ginger's latest envelope wondering what she had sent me this time. After cutting it open, I upended it and allowed the contents to drop out onto the bed. The red silk and lace bra and thong (thong!) didn't surprise me since I'd already been down that rabbit hole. What did surprise me was the red silk and lace garter belt and smoke-colored stockings. I grabbed my phone and wasn't surprised to see Ginger was online seemingly waiting for me to tap in. She must have seen my profile light go green because a second later she said,

"Morning Sweetie!! Looking at your latest frillies?"

"Yeah and wondering about these stockings." I replied.

A YouTube link popped in along with her saying, "It's easy sweetie. Just roll them up slowly. Can't wait to see how they look on your legs."

For the millionth time I wondered what I had gotten myself into. I decided to get the easy part out of the way and put the bra and thong on. The bra was a bit easier having done it the day before and after two days of wearing tanga panties the thong strap was definitely more noticeable but not unexpected.

I then pulled the garter belt up around my waist, and by around my waist I mean more around my chest. I had to pull it up that high because otherwise the straps would have dangled around my knees, and I knew that wouldn't work. With the garter belt in place, I watched the short video Ginger sent me a couple of times before slowly rolling the stockings up my legs. After a few attempts and re-dos to keep them from getting runs I had them in place. They weren't perfect but were as good as they were going to get with the little time I had left.

I grabbed my phone and walked to the mirror. As I walked, I could feel the belt straps and stockings pulling on my legs as well as my erection pressing against the front of my thong. I quick snapshot from the front and another from the back and I sent them off to Ginger. A few seconds later she sent back,

"Wow... your legs look good in stockings... and your tushy looks good,"

I felt myself going red to match my lingerie as I grabbed my clothes out of the closet. Not even thinking I grabbed my red button-down shirt and pulled it on. As I pulled my clothes on, I quickly typed out, "Got to get to work."

"Of course, Sweetie!!!" she replied. "Talk to you later."

As I got in the car to drive to work, I immediately felt the garter straps pulling against my legs and my erection pressing firmly against the silk thong. I shifted and felt the silk rub my cock causing it to throb and inch up a bit. As I felt my cock inch up, I was surprised to feel the strap pull a little tighter between my cheeks. As I backed out of my driveway I wondered for the millionth time what I had gotten myself into and how I was going to get through this day with all these sensations down below.

I got to work and tried my best to ignore the simultaneous sensations of the garter straps pulling against my thighs and the tug of war between the front and back of my thong as I walked across the parking lot and into the office. All of these movements were naturally keeping me rock hard, and I had to put a conscious effort to walk normally.

As I got into the office, I made my usual trip to the breakroom to refill my coffee I saw Casey in there clearly having trouble with the coffee maker. She had obviously been having trouble with it for at least a few minutes because she suddenly swore and whacked the side of the machine. She then turned away in frustration and that's when she saw me.

"Oh, hi Ronnie." she said going slightly pink.

"Having trouble?" I asked.

"Stupid thing doesn't want to brew." she said sounding frustrated.

I walked over to the machine and said, "Let's see if we can figure it out." After a few seconds of examination, the problem was apparent. I picked up the unplugged cord and turned to face Casey and said, "I think we found our problem."

Casey suddenly looked mortified and said, "Oh my god, I'm such an idiot."

"You're not an idiot; you just haven't had your coffee yet." I told her as I plugged the machine back in and hit the start button. Within seconds a steady stream of hot fresh coffee was pouring down into the carafe. While the coffee brewed, I grabbed a paper cup and added cream and sugar in the amounts that I knew Casey liked. Once the pot was full, I filled the cup and stirred in the mix good before handing it to Casey. As I refilled my travel mug, I watched her take a greedy pull on the coffee I just handed her and a look of relief flood over her face.

"You're the best Ronnie." she said before taking another greedy pull on the coffee. "I feel so stupid."

"You're not stupid." I said reassuringly.

Casey and I then made our way back to our area and I got my day started. After a couple of hours of examining a large stake of invoices I heard my phone beep. I looked at it and saw it was Ginger messaging me on the app.

"How you doing sweetie?" she asked.

"Pretty good." I said. "Just keying in invoices."

"How about down below?" she asked with a wink emoji.

Just like the previous days it was an exercise in how well I could sit still. If it sat still my erection would start to go down, but any movement would immediately go right back to full staff and the tug of war with the thong strap pulling between my cheeks would start over again. I typed this out and sent it to Ginger. A few seconds later several cry laugh emojis appeared.

"LMAO." she said. "Glad you're having fun in your lingerie. By the way I hope you don't have to work late because you're going shopping after work. Unlike you I'm not made of money and can't keep sending you sexy lingerie to wear, and I know you don't want to end our fun, so you'll have to go shopping. There's a great place on the east side that will give you what you need. I'll send you a list later."

I was suddenly nervous. Ginger had said this moment was coming, but I was hoping it would come a little later. I didn't know how I would react to buying lingerie. It had been a while since I had bought lingerie and that had been for a girlfriend. Now I had to buy lingerie for myself! And while wearing lingerie under my clothes!

I picked up my travel mug to take a swig of coffee only to discover that it was empty. I decided then a break was in order. I stood up and headed out of my office. As I passed Casey at her desk, I noticed she had a slight smirk on her face. As I got down the hall, I decided a stop in the men's room was in order before getting fresh coffee. The walk had, naturally, re-ignited my erection, so I needed no reminder to step into a stall rather than up to a urinal.

Once I locked the stall door behind me, I unzipped my pants and made to lower the waistband of my thong and do the now usual routine of waiting for my cock to get soft so I could pee. It was then that I noticed I had a problem. The waistband of my thong was trapped behind the garter belt I had on. I stood there a few seconds wondering how to get around this predicament. My first thought was to drop the garter belt out of the way, but that would have taken too long and would require removing my pants. Removing my pants in the men's room wasn't an option even in a locked stall. After a few more seconds of thought I pulled the thong to the side and slid my cock out of the leg hole. While it wasn't exactly comfortable it worked and after a few minutes I had softened enough to be able to pee, although at a somewhat awkward angle.

After relieving myself I tucked myself back in and had barely zipped myself back up before my cock had returned to its erect state. After washing my hands and refilling my coffee and made my way back to my office. As I approached, I saw Casey still had that amused smirk on her face. As I passed her desk she said,

"You ok boss?"

"Yeah fine." I said. "Just needed to take a leak and refill my coffee."

"Your phone has been beeping." she said.

"Oh ok." I said as I headed into my office.

Once back in my office I looked at my phone and saw a couple of messages from Ginger. The latest one said, "Where'd you go?"

I quickly typed out what had happened with my garters and thong in the men's room. A few seconds later the expected laugh emojis popped up from her.

"LMAO." she said after that. "Now you know why women wear the panties over the garters. I guess I could have explained that to you, but then what fun would that have been?!"

I should have felt embarrassed but actually found myself amused. I guess I was so far down the rabbit hole on this that it didn't matter. Of course, she'd 'forget' to explain the physics of putting the panties over the garters.

Just after lunch as I was going through the latest stack of invoices I heard my phone beep again. Two words greeted me that shouldn't have surprised me but did.

"Desk selfie."

Here we go again I thought as I slid my chair back and unzipped my pants. The folds, naturally, easily parted due to my erection straining against the silky thong I had on. As quickly as I could I snapped a shot and sent it off. Once again, as though divinely designed, I barely got myself zipped back up when I heard the door pop open and Casey walked in.

"Here's the latest expenses from the department heads boss." she said cheerily.

"Thanks Casey." I said as I took the reports from her.

"You ok boss?" Casey asked. "You look a little tense."

"Yeah I'm fine." I said. "Probably just looking at screens and numbers too long." I said trying to sound natural.

Over the next couple of hours my tension levels did rise but not due to Ginger fucking around with me, but because due to a billing issue I couldn't get the ledgers to balance like they're supposed to be. At one point after reading and re-reading the ledgers and the invoices I tossed a stack of invoices down on the desk in frustration and put my face in my hands and shut my eyes for a few seconds.

A few seconds later I heard the door open and looked up to see Casey stepping in again. Her face suddenly took on a look of concern as she saw me.

"What's wrong boss?" she asked as she came over to me.

"These people in billing really need to get their lives together." I said. "Someone doesn't know how to fucking proofread and now I've got to find their mistake to get the ledgers to balance."

As I finished my small vent session Casey walked around behind me and suddenly, I felt her small hands on my shoulders. She started massaging my shoulders and I started to feel the tension start to leave me.

"Just relax boss." she said gently as she continued to rub my shoulders. After a few minutes I was feeling more relaxed and it was then I fully realized I was being massaged by my beautiful secretary and suddenly my hormones began to reassert themselves. As the tension was leaving me my arousal was kicking back up and I felt my cock growing up front and the thong strap pulling tight between my cheeks again. I hadn't even noticed I had gone soft with all the frustration I was feeling.

As I felt the thong strap pulling tight between my cheeks again I suddenly remembered what I was wearing underneath and hoped Casey couldn't feel the bra strap under my shirt and undershirt. But it was too late for that, and I couldn't have stopped her if I wanted to.

As suddenly as she started Casey stopped rubbing my shoulders and asked, "Better?"

I turned to face her and said, "Much better. You're too good to me."

She gave me a slightly devious smirk that sent another thrill between my legs before saying, "I hope you remember that when it's time for evaluations."

I smiled sheepishly and said, "Don't worry I will."

Another devious smirk and she said, "You better." That sent another throb down below and another tug at the strap between my cheeks. In an effort to distract myself I reached forward and picked up another invoice as Casey turned to leave. A quick perusal of the invoice showed me that it was the one I was looking for.

"This is it." I said causing Casey to turn back to face me. I placed my finger under the line where the numbers were transposed.

Casey smiled at me before saying, "You're welcome." before turning on her heel and walking out with a confident air about her that sent another thrill between my legs.

After getting that invoice corrected and being able to balance the ledger and sending a nice nasty email to billing emphasizing the need to proofread invoices before keying and posting I decided enough was enough for one day even though it was only 4:30. I shut my computer off and opened my office door to leave. Coming up behind Casey at her desk I said,

"I think we've done enough for one day Casey."

She looked back at me and said, "But it's only 4:30 boss."

"I'll put your time to 5:00. You earned it helping me find that bad bill." I told her.

Casey didn't need telling twice saving her work and shutting off her computer. "See you in the morning boss." she said cheerily as we made our way out.

Once in my car I pulled my phone out and told Ginger I was done working.

"Who's a naughty boy cutting out of work early?" she asked.

"I thought you wanted me to get done so I could go shopping." I said.

"Of course sweetie." she said. "I'm sending you the address of a great lingerie store and what I want you to get." A few seconds later an address appeared as well as pics of lingerie. I was aroused and worried as I gazed at the pics. I then typed the address into my GPS and headed to the store.

About twenty minutes later I pulled into a strip mall and up to Lacey's Lingerie. I couldn't help but feel a stab of nervousness as I walked in. The store was small and nearly crammed full with rows of hanging racks with seemingly every type of lingerie one could imagine. The walls were covered with posters of women in lingerie higher up with the lower part containing hooks containing more lingerie and other sexual paraphernalia. I was somewhat lost looking at the women on the posters when I heard a voice.

"Hi there. Can I help you?" she said.

I turned to see a curvy red head woman walking towards me. She was wearing a tight fitting red and black silk corset that showed off at least two inches of her curvy stomach and a pair of tight jeans with a red thong strap visible on one side. While I wasn't usually big on larger curvy women I couldn't deny she was attractive and felt the expected reaction and tug of war in my pants.

As she came up to me I pulled out my phone and showed her the picture of the yellow floral print silk and lace teddy/body suit she had sent me. "Yes do you have this?" I asked trying to sound confident.

She gave me a knowing smile as she said, "We do they're right over here. You can follow me." She then turned and I was memorized watching her big curvy rear end in those jeans move away from me. Not wanting to be caught staring I quicky began to follow her. We reached the end of the narrow aisle and I saw the item several of the item in question hanging on the rack.

"What size do you need?" she asked turning back to face me. I then found myself in another predicament. The picture Ginger sent me gave me no information as to what size to use. The sales lady clearly saw my predicament and said, "So roughly how big is she?"

"Roughly my size." I said knowing I was probably giving myself away, but what choice did I have?

"I see." she said with a knowing smile. She then turned to the rack and pulled one of the teddys off of it and holding it up in front of me before saying, "I think this one should do." I took the hanger from her as she said, "Anything else I can help you get?"

"Yes." I said again consulting my phone. "White lace hold up stockings."

"This way sir." she said again giving me that knowing smile. A couple of aisles over she selected a couple of packs of lace hold up stockings and saying, "I think these will do the job."

The sales lady and I spent the next thirty minutes or so getting many sets of bras and panties, multi pack girly panties and thongs, silk camisoles, all from the list that Ginger had given me. As we were headed to the checkout I saw a small rack of novelty panties. I couldn't help but stop and quickly examine them. One pair stuck out to me. They were white cotton and styled to look like men's briefs with pink leg and waistbands and a mock fly. I picked them up and on the back panel it said in pink letters 'I heart boys'

The sales lady saw me looking at them and said, "Go ahead and get them. You know you want to." I added them to my large selection and moved to the checkout counter. I tried not to appear shocked as the bill came to just over $200. As the sales lady bagged my purchases she smiled at me and said, "Hope you have fun with all of this."

I thanked her and made my exit. Once I got home, I unpacked everything and laid it all out on my bed. I took a picture of it and sent it to Ginger.

"Very good sweetie." she said after seeing the picture. "Looks like you found everything."

"Yes. Lacey was very helpful." I said.

"Hmmm. You like Lacey?" she asked.

I suddenly felt a little awkward, I know as though buying lingerie clearly for myself while wearing it wasn't. "She was very helpful." I replied.

"You naughty naughty boy." Ginger said. "I can just see you in there fawning all over Lacey. You're just a regular playboy I see. What would that cute little secretary of your think if she knew you were buying a butt ton on lingerie for yourself?" I gulped not wanting to think about that.

Before I could type out a response another message chimed in. "What's that white pair of panties in the corner?"

Phew... no more teasing about Casey. "I saw them and couldn't help myself." I said and took a closer snapshot of the boy style panties front and back and sent them to her.

I expected some laugh emojis or some quip about picking them out but she simply said, "I want to see you in those... NOW!"

I slowly undressed pulling off the bra, garter belt, stockings, and finally thong (feeling a rush of relief as the strap came out from between my cheeks.) I then picked up the cotton boy briefs and pulled them on. Although they were styled like men's briefs, they were clearly cut for women sitting pretty low on my waist and I was forced to tuck my hardon sideways to keep it from sticking out. I then grabbed my phone and went to the mirror and snapped a shot from the front and back and sent them to Ginger.

"Very cute." she said with a love emoji. "I see flirting with Lacey and your cute little secretary has left you a bit worked up."

"Yeah, because wearing all that lingerie wouldn't do it." I quipped back.

"Not for a real man it wouldn't." she shot back. A real man would get hard seeing it on a woman, not by wearing it at the direction of a women he doesn't even know (or does he?)." This was the second time she had alluded to the fact that I might know her. I racked my brain for a few seconds wondering who in my circle of acquaintances would want to do me like this. I didn't have a lot of time to think about it because another message popped up.

"You know I'm only teasing you (for the most part)." she said. "But now you've got a lot of lingerie to wash and I'm sure you didn't notice that most if it is handwash only."

I spent the next couple of hours gently washing each of the garments that Ginger had me buy under her supervision. By the time I was done nearly every available spot I could find in my bedroom and bathroom had become a makeshift clothesline to hang the various garments on. I sent several snapshots of my lingerie hanging from every available spot and sent them off to Ginger.

A few seconds later, "Wow... would be great for someone to pop in unexpectedly."

The thought had me going pink, especially since not only did I have all of my lingerie hanging out conspicuously, but I was only wearing the cotton boy panties I had modeled for her earlier.

"Why do you get off on the idea of embarrassing me?" I asked.

"Don't act like the thought doesn't turn you on." she shot back. "I know you watch Panty Jane's videos where she mocks him for being so hard wearing her lingerie, so I know you like the idea of a strong woman controlling you with panties."

Once again I was taken aback. How did this mystery woman know I watched Panty Jane's videos? Clearly, I had let something slip somewhere and allowing Ginger to get a glimpse of my kinkier side, but where? And how?

The rest of the night passed for the most part uneventfully with some teasing and banter between Ginger and I. Ginger the tease was back allowing me no relief to the tension that had built between my legs saying the day before should have been more than enough release for the time being. So, I crawled into bed with just my boy brief panties on and tried to ignore the erection between my legs as the events of the day flashed through my mind again as I tried to get to sleep.