Panty Delivery Boy Pt. 01

Special thanks to Martin594 for providing the idea for this story.

I had no idea what was in the box, only that it was expensive enough to require a signature on delivery. I pulled up to 321 Holland drive in the upscale Kingsborough Estates neighborhood and couldn't help but admire the perfectly and almost too green lawn and all of the shrubs and flowers that made it look ready for the next edition of Better Homes and Gardens. As I got out of the delivery truck I couldn't help but feel a little out of place in my khaki shirt and shorts that made up my uniform.

I grabbed the box from the back of the van and headed towards the front door passing the dark blue Jaguar convertible coupe as I walked. I couldn't help but think that that car probably costs more than I make in a year as I passed it and walked up the porch and rang the bell. As the door opened, I had to control myself from letting my jaw hit the floor below me. No exaggeration I was face to face with one of the sexiest women I had ever seen. Long blond hair formed a cute round face and deep blue eyes. Her body formed a perfect hourglass figure that the tight black t-shirt and leggings did nothing to conceal. The shirt was so tight and skimpy it showed not only the outline of the sports bra she was wearing but showed a good two inches on her sexy flat stomach.

"I have a delivery for Mrs. Sandra Pembrooke." I said trying not to sound like a nervous adolescent talking to his first crush.

"That's me." she said smiling and sending more butterflies into my stomach. Her teeth were paper white and perfect just like the rest of her. "Come on in." she added and I meekly followed her in carrying the box. As soon as I cleared the door she shut it behind me and turned to me and said,

"You can set the box there." indicating a small table in the corner of the foyer. I set the box on the table as she told me. I then took my tablet off the top of it and pulled out the stylus and said,

"Now if you can sign here Mrs. Pembrooke." as I held the tablet out for her.

She smiled again as she took the tablet and began to sign. "Please call me Sandy. Mrs. Pembrooke makes me sound like I'm 80 years old."

'You'd be the hottest 80 year old I've ever seen.' I thought to myself as I watched her slender sexy hand complete with sparkly purple nail polish move the stylus across the tablet. She handed the tablet back to me and said,

"I'm glad this came so fast. It's a gift for my husband's birthday."

"Oh really?" I asked curious myself as to what the small box held that required a signature delivery and wanting to prolong my eye gazing at Sandy.

"Oh yeah." Sandy said. "My husband loves rare and expensive liquor. And this is supposed to be 40 years old. Want to see?"

My curiosity again got the better of me and I nodded. I was rewarded with a nice view of Sandy's curvy rear end in her way too tight leggings as she turned and made to open the box. As she forced a fingernail under the tape I intervened.

"Allow me." I said as I pulled a box cutter from my pocket.

"Such a gentleman." she said with a smile as she let me cut the box open. Under copious amounts of packing peanuts and wrapped in bubble wrap was indeed a bottle of what looked like fine top shelf alcohol. I held the bottle up so we could both read the front label. As we read we learned the Flintrock Scotch was over 40 years old.

"Wow." I said as I set the bottle down on the table next to the open box. "I know that wasn't cheap."

"Yeah and he better like it." Sandy said in a tone that I knew was playful but not playful. "It took me a while to find something I know he hasn't tried."

As much as I wanted the conversation to continue I knew I had a van full of deliveries to make and talking to a married woman about her husband's birthday gift seemed a bit untoward to me, so I decided to make my exit.

"I'm sure he'll love it." I said. "Well I've got to get back to it."

"Oh of course." Sandy said looking slightly abashed. "I'm sorry I didn't mean to hold you up."

"No worries." I said smiling sheepishly before heading to the door. After a quick exchange of goodbyes I was back in my van headed to my next delivery. The rest of the day I couldn't get the image of Sandy and her incredible body and smile out of my mind. This was both a good and a bad thing since while it was a pleasant thought it made my shorts quite snug and I was more than ready for a little self fun when I got home that evening.

***

It was a few weeks later and I had all but put Sandy and how sexy she was out of my mind. It didn't even hit me when I had several other packages to deliver on the same block that she lived on. As I dropped one package off on the front porch I quickly marked it as delivered on my tablet and pulled up the next drop on my run. That's when I saw the name Sandra Pembrooke and it all came back to me. As I read the details of the delivery I couldn't help but be a little disappointed that it wasn't a sign for delivery so I wouldn't have the opportunity to talk to her again.

As I made my way down the block I, naturally, had flashbacks to our last encounter and by the time I got to her driveway my shorts were a bit snug. I got out of the truck and grabbed the small envelope and headed for the front porch. As I walked up the driveway I noticed her Jaguar wasn't there and figured she was out. That wasn't a big deal since it wasn't a sign for delivery, all I had to do was leave it on the porch. I set the package on the front porch next to the front door where it would be easily seen and turned to head back to the van. As I got part way down the steps I heard the front door open and a voice say,

"Oh thank you."

I turned to see Sandy and again had to control myself to keep my jaw from hitting the ground below me. She was wearing a skimpy white spaghetti strap tank top that did nothing to hide the white lace strapless bra she had on underneath that and a pair of black cotton shorts that I swear weren't as long as my boxers. She'd clearly been spending some time in the sun having a nice tan on her face, arms, and legs.

"You're welcome." I said again trying not to sound awkward and trying not to look like I was leering at her, even though I was.

We were both turning to head our separate ways when inspiration suddenly hit me. "Did he like the scotch?" I asked.

She gave me a puzzled look before saying, "Huh?"

"Your husband." I said. "Did he like the scotch you got him?"

Her eyes got big for a moment as it all came back to her. "Oh yeah." she said with a slight giggle. "Sorry, blond moment. But yeah, he loved it, said it tastes wonderful."

"Glad he liked it." I said and we both headed our separate ways.

***

Over the next several weeks I was surprised to find myself several times delivering packages to Sandy's house. While many of those deliveries (much to my disappointment) I just dropped them off on the porch and left with no interaction with her, some of them we would stop and chat for a few minutes before I needed to get back to my route. Part of me started wondering what she was ordering, but didn't want to appear nosy, so I didn't ask. My guess was that they were movies given the feel and weight of the envelopes I was delivering. I wouldn't have been surprised to learn that Sandy and her husband were movie fans and had a home theater in that small mansion they lived in.

One afternoon I found myself once again at Kingsborough Estates and was hoping that there was an envelope for Sandy in there and I would get a chance to chat with her. After delivering several other packages I couldn't help but smile as I saw her name as the next drop on my tablet. I smiled again as I pulled up to her driveway and saw her Jaguar in the driveway. I grabbed her envelope and briskly walked up the driveway. By this point Sandy seemed to make a point of receiving the deliveries herself if she was there instead of grabbing them from the porch despite not needing to. So, I wasn't surprised when she opened the door as I started up the front steps. Also by this point I was used to the attire she wore so it didn't take as much work to keep my jaw from hitting the floor when she appeared wearing a white tennis skirt and visor. That didn't stop me from wishing for a sudden gust of wind though.

"Hi Willy." she said with a smile. I usually went by Will and that's what was stenciled on the front of my uniform shirt but she had taken to calling me Willy and I didn't have the heart to correct her. I mean how can you contradict the hottest blonde you've literally ever seen?

"Hi Sandy." I said returning her smile.

"I'm glad this came quickly." Sandy said as she took the envelope from my hand.

"Glad I could help." I said.

"You have no idea." she said with somewhat of a sigh. Even being a simple delivery driver and even in my hormone addled state in Sandy's presence I could tell she had something on her mind and it wasn't good.

"You ok?" I asked.

She eyed me for a second as though trying to determine if she should talk to me or not. She then gestured for me to sit in one of the rocking chairs on the porch. Once I sat down she said, "I just get bored around here."

"Bored?" I asked wondering how anyone could get bored living in such luxury.

"Yeah." she said. "Don't get me wrong this is a great place, but it gets boring when you're by yourself so much. I'm sure you can tell my husband is away a lot."

"I'm sorry." I said not sure of what else to say at these revelations.

"And even when he's here he's..." she said but stopped before finishing and then turning her face to stare off into space.

"He's what?" I asked my curiosity getting the better of me.

She looked back at me with a pensive look on her face again appearing to consider whether or not to continue to confide in me. She took a deep breath and said,

"Look." she said slowly. "I love my husband, I really do, but he's a bit... How can I say this? A bit boring in the bedroom."

I wasn't sure what I was expecting to hear, but this certainly wasn't it. I wondered how any red blooded man could not want to please a hot woman like this as much as she wanted. Again I wasn't sure what to say.

"Boring?" I asked tentatively.

"Yes." she said blushing slightly. Another deep breath and she said, "He's about as old school as they come as far as sex. Missionary is his favorite. No sense of adventure or desire to explore. Took ages of begging for him to let me be on top."

I felt my shorts tightening again as I listened to Sandy talk about her sex life with her husband. I suppressed a desire to pick her up and carry her inside and ravish her like she clearly wanted to be. Thankfully, she continued keeping me from trying find something to say.

"I have a lot of ideas I'd love to try with him, but he straight up refuses." she said with a slight sullen tone in her voice. She then gazed around as though there were spies in the bushes before saying, "I'll let you in on a secret. All these packages you've been brining me are porn vids."

How many times can a guy be shocked in one day?! I mean I was right; they were movies just not the ones I was thinking about. The thought of Sandy watching porn and getting off sent another thrill between my legs.

"I'm sorry, I wish I could help." I said.

"You're sweet Willy." she said giving me a sweet smile that did nothing to help the tightening sensation between my legs.

She then stood up and I followed suit. She looked at me and said, "I'm sorry, I shouldn't have burdened you with my problems. You should probably get back to work."

"Unfortunately yes." I said. Then before I could react she threw her arms around me and hugged me. It was the first time we ever touched. I quickly returned the hug and held her for a few seconds before she pulled back.

"Thank you." she said again smiling at me.

"Any time." I said again trying not to sound like a befuddled adolescent.

To say I left with a world class erection after that would be to state the complete obvious. I couldn't get the rest of my route done fast enough and once I got home, I had a nice edging session that culminated in a massive orgasm, one of the best I had had in a long time.

***

After a few weeks of no deliveries to Sandy I was starting to think maybe she was a bit embarrassed at having said so much to me. I was content to let things be as is when I saw her name pop up on my tablet one afternoon. By luck or divine design, she was my last stop, so a lengthier stop wouldn't be as big a problem. I couldn't help but walk with a small spring in my step as I walked up the path to her front door.

As I had come to expect she opened the door with a big smile on her face and wearing a t-shirt and jeans that looked painted on.

"Oh Willy I'm glad you're here." she said.

"Me too." I said and I wasn't lying.

She took the envelope from my hand and then did something completely unexpected. She turned back to the door and said, "You want to come in?"

"Sure." I said trying to sound casual. I hadn't been inside since delivering that first package she had to sign for. I followed her in watching her curvy rear end move back and forth in those jeans that it must have taken magic to get on. I followed her into the main living room which looked larger than my whole apartment. The room was light and airy with white sofas and chairs lining around a central coffee table. She sat down on the sofa and indicated that I should sit next to her.

Once I sat down next to her she turned to me and said, "The last time you were here you said you wished you could help me."

"That's right." I said unsure of where this was going but hoping it was going where I thought it would.

"I should explain to you that I have some pretty kinky fantasies." she said.

"Ok." I said liking the idea and so did my cock if the tightening sensation between my legs was any indication.

"Let me give you a glimpse of the type of videos I've been ordering." she said before tearing opening the envelope I had just delivered to her. She quickly got the envelope open and upended it allowing the DVD to drop out onto the coffee table in front of us. She picked it up and handed it to me.

My eyes widened as I looked at the cover. The title was Panty Jane's Adventures Part 4 and the illustration showed a fierce dominant looking woman in lingerie towering over a man also wearing lingerie on his knees. I flipped the case over the back showed more small screencaps of this man clearly in submissive positions to the lady still wearing women's lingerie. A quick perusal of the text said that he had no idea what he was getting into when he met Jane at the local pub or what it would take to please her.

I set the DVD down after reading the back and looked over at Sandy. Shocked isn't even the right word to describe how I felt. Sandy gave off this innocent girl next door vibe and here she was showing me she liked porn with dominant women and cross-dressed men.

"Wow." was all I could say as I set the DVD down.

"Surprising right?" she said. "Sweet little Sandy wants to be a dom. I think that's what scares my husband off of it."

"So you want to be like Panty Jane?" I asked.

"Oh yes, to have that level of power over a man is a massive turn on for me." she said.

"Really." I said not sure what to say.

"Yes." she said with a clear tone of arousal in her voice that sent a shiver through me. "That and something about a man wearing girly lingerie just gets me all tingly between my legs."

Before I could say anything she looked at me and said, "That's where you can help."

I gulped a little before saying, "I can."

She then peered into my eyes and said, in a low sexy voice "I know you're attracted to me. I felt your hardness when I hugged you last time you were here. And I've seen you eying me when you thought I wasn't looking. And the growing bulge in your shorts every time we talked. Sorry Willy you're not as slick as you think you are. So, I know you'd be more than up to doing a little shall we call it live action roleplay?"

"Live action roleplay?" I said still somewhat in shock.

"I think it would be fun. Don't you?" she asked still sounding sultry.

"What about your husband?" I asked.

"What he doesn't know won't hurt him." she said. "He had his chance but refused to play. You look like a much more willing participant."

Again, before I could say anything she said, "Follow me." She then stood up and I meekly did the same and followed her. I followed her up a long winding staircase that wrapped around the entirety of the entry hall up to the second floor. Down at the end of a long wide hallway we entered what was clearly her bedroom. This room too looked larger than my apartment and was dominated by the massive king-sized bed in the center of the room.

She led me passed the bed to her dresser that looked three times the size of a regular dresser. She opened one of the top drawers and I was face to face with what had to be dozens if not hundreds of pairs of panties. She let me gaze for a few seconds before reaching in and pulling out a pair of silky coral pink panties.

Shutting the drawer, she held up the panties before my eyes. They were coral pink with very thin white lace leg and waistbands and a small red rose front and center of the waistband. She flipped them around and I saw that while they had a full seat there was a scrunched seam running up the center clearly designed to accentuate the wearer's cheeks. My perverted mind quickly went into overdrive as images flashed into it of Sandy wearing those panties and creating the expected result between my legs.

Her voice pulled me back to reality as she said, "I know you're probably wondering what I look like in these panties, but these aren't for me they're for you."

"For me?" I asked in a weak voice unable to hide my shock any longer.

"Yes, sweetie they're for you to wear for me." she said. "And don't act like you don't want to. That banana in your shorts tells me otherwise."

When I didn't respond she gazed at me again with that bedroom eyes look before folding the panties up and stuffing them in my shirt pocket. "Tell you what." she said confidently. "I've ordered another movie. Says it'll be here in 3 days. If you want to do more than gawk at me and have small talk when you bring it wear those panties. Now I'd love to continue this, but I've got a dinner date with a girlfriend."

I followed her out of the room and back down the long winding staircase to the first floor. I was about to open the front door to leave when she told me to wait up. She ducked into the living room and quickly re appeared with the DVD I had just delivered to her.

"Take this home and watch it." she said with a glint in her eye. "And see if it's something you'd like to toy around with with me."

We then walked out the front door and as she made to get in her Jaguar she said, "See you next time Willy." I nodded and got in my van and headed back to the warehouse to turn it in for the day.

Naturally, for the rest of that afternoon and evening my mind was on a constant loop of what had transpired between Sandy and I. I mean yes we had flirted around a bit and wasn't completely surprised that she could tell I was attracted to her. But her wanting me to be a live action roleplay model for her so she could act out her fantasies that her husband wouldn't want. That was a whole new ball game and one I'm not sure I wanted to be a part of. The last thing I needed was to be a homewrecker.

After eating a quick dinner my mind was still racing trying to decide what to do with Sandy and her suggestion. It was then that my eyes landed on the DVD she had told me to watch. Like most men I'm always down to watch a bit of porn even if I knew it wasn't what I usually looked at.

I grabbed the DVD and headed to my bedroom. I always figured if I was going to watch something that I'd probably end up jacking off to I may as well be comfortable. I popped the DVD out of the case and dropped it into my DVD player. For not the first time I was glad I had splurged and gotten myself a 60-inch TV for my bedroom. As the menu came up, I stripped down nude and laid down on the bed. 'Here goes nothing.' I thought to myself as I hit play.