The Shopping Spree

It was the day before Thanksgiving, and everyone at the office knew we'd be getting the afternoon off. I was finishing up my work for the day when I received the text that would change me forever.

"Meet me at the far end of the WalMart parking lot at 2:30. Don't be late. And don't wear underpants."

My cock knew immediately who it was: Jim. Since meeting him several months ago, he had become my semi-regular feeder. His cock, while average in size, was fully functional, which was a decided plus for a man his age, and fed me thick, tasty cum on those occasions we were able to meet. He was slightly older than me, with balding hair, a relatively smooth face for his age and eyes that blazed with intelligence.

Given our scheduling issues, we grabbed feeding times when we could. Usually, we made arrangements via email and met at the local ABS, Pegasus, which was located within a lunch hour drive of both our work locations. He was definitely in charge of the feedings, but I requested them far more frequently than he did. Jim was able to go a week or two between meetings. For me the hunger returned within a day or two of being fed.

It had been a week since we had last met, so I was delighted to receive the text. I was also puzzled. Normally, we would meet in the theater room of the ABS. And he had never before given me instructions about what [not] to wear. Nor had he been so emphatic about timeliness. For some reason, that gave me a thrill: he knew I was submissive. Was he, perhaps, going to make me pleasure him in his car in the parking lot? It would be dangerous, but I trusted him to take care of me and not to get us arrested.

Before leaving, I stopped at the Men's Room and entered a stall. Thankfully, no one else was there. I sat on the lowered toilet seat and slipped out of my shoes. Then, I took off my pants quickly and hung them on the door hook. Next, I lowered my underpants and folded them. Hearing the door open, I slipped into my shoes and hoped whoever had entered wouldn't notice I was wearing socks with no pants legs showing.

He went into the next door stall and closed the door. I checked my watch: 1:53. I didn't have time to wait for him to finish his business; I would have to chance it. I squeezed my cock and licked the precum off my finger, savoring the flavor. I was wearing khakis and didn't want to get them wet. I slipped out of my shoes again and put on my pants, being careful to tuck my cock down. After stuffing my underpants into my right pants pocket, I put my shoes back on and walked out, remembering to flush and wash my hands. I checked the mirror to see if he was watching, but I couldn't tell. Oh, well...

I returned to my cubicle, grabbed my pack and left, walking down the five flights of stairs to get some steps in. My cock rubbed against my pants in a most delightful way that threatened to undo the whole tuck. Note to self: when going commando, don't walk down stairs if you don't have to. I made it to the carport and my car and put the pack in the floor of the back seat, making it as inconspicuous as possible. As soon as I was buckled in, I unzipped, pulled out my cock and cleaned off the pre-cum again. This was not going to cut it: my pants would be stained before I met Jim. I pulled out a tissue and wrapped it around my cock before returning it to my pants.

The drive to Walmart was uneventful, or as uneventful as it could be with my cock feeling every bump of the road and my mind racing with visions of my head in Jim's lap slurping up precum from his mouth-filling mushroom head. I had to tune in to a sports talk station to keep my mind focused on the task at head: getting to Walmart in one piece.

Somehow, I made it to the WalMart. Cruising slowly around the far reaches of the parking lot, I looked for Jim's SUV, but didn't see it right away. I circled closer to the store until I found his car, parked near the front of the store. I was puzzled: with all the foot traffic, there's no way I could go down on him, even in the SUV, without the very real risk of someone walking by and glancing in. The parking lot was filling up with pre-Thanksgiving turkey hunters; I had to drive to the rear to find an open parking place. I heard a ding from my phone and, when I parked, I saw a message from Jim.

"Come to my car and hop in. Bring your backpack and plan on leaving your car there for a while."

I took a sharp breath when I read that. Apparently, I was in for more than a blow and go. Jim's consideration was evident: he wanted me not to worry about anyone taking my laptop. It was also clear that I wouldn't be serving him in his car. Was he going to take me to Pegasus and use me there? Oh, yes, please!

I grabbed the pack from the back seat, locked the doors, and started for his car, thankful I was wearing my jacket, as the wind was picking up. A brisk walk, and I arrived at the passenger door of his SUV. The back door slid open, and I heard his raspy voice say, "Put your pack in the back and hop in the front."

I did as he said, thankful that he had started the car and kept it warm. I sat down, smiling appreciatively as I felt the heated seat on my tush. I turned to Jim and the smile died down. I hadn't seen him look so serious since...ever. What was wrong? Had his wife found out? Had he found someone better? Was he tired of me?

"Sir, is everything OK?"

"I think it is, Soma. I have a surprise for you today and I hope you like it."

"I love surprises, Sir," I said, "especially when they come from you. Are we going to Pegasus? Are you going to put on a show with me?"

"Nope. We're going shopping."

"Shopping, Sir?" I was sure he could hear the disappointment in my voice. Here we had an afternoon off for play and we were going to WalMart?

"Yes, but it's not what you think. First, I need to know: do you trust me, Soma?"

"Of course I do, Sir. You've treated me well since we started meeting."

"Good. This is going to be a very special shopping spree for you. I want you to meet some friends of mine, who have the same need for a good cocksucker as I do. They're mostly in the same boat with me: we're not spring chickens and we're not the sort that guys on Squirt want to meet. So far, I've been the only one to luck out."

"You want me to drain their cocks, Sir? You know I'm up for that any time."

"There's a little more to it, but we'll talk about that later. Here's how this afternoon is going to go: you and I are going shopping. You'll be blindfolded while I drive. When we arrive, I'll take off the blindfold and we'll go into the store. I'm buying you something to wear. You'll obey my instructions without question.

"After the purchase is made, you'll put on what I bought you and thank me by drinking down my cum. When you've finished, you'll put on the blindfold and I'll take you to the next store. One of my friends will be waiting for us there. I'll hand you off to him and leave. He'll take you into the store and buy you another clothing item. You'll put it on and thank him the same way you thanked me. He'll pass you on the next man. Lather, rinse, repeat. Are you OK with this?"

"You know and trust these men, Sir? They're all clean and healthy?"

"I've known them for years. They're neighbors and coworkers. I've told them a lot about you and they really want to feel your lips on their cocks. They haven't had a good blow job for a very long time."

Hmmm.....multiple feedings? And it sounds like they'll have big, tasty loads. What's not to like?

"Since they're your friends, Sir, I'll be happy to make the sacrifice and make them happy."

"Yeah, Soma, I really appreciate you taking one for the team...or should I say, several?" I was glad we understood each other.

He added, "Oh, there's one more thing: you are not to question anything they tell you to do. This is your last chance to back out. Once you commit, I'm making the call to them to set this in motion and there's no turning back. Once you start on this trip, if you hesitate, if you refuse to do as you're told, you'll be returned directly to me and our relationship will be over. I won't have you wasting my friends' time and disappointing them.

"If this is not for you, tell me now. We can continue as we've been doing and you can go back to your car. Or you can take this to the next level. The choice is yours." He looked at me intently.

I lowered my eyes, not sure now what to do. He was giving me an ultimatum. I knew if I backed down, our times together would peter out. And this was what I had fantasized about for years. But what happens when fantasy turns into reality? How many times does that actually end happily ever after? And every person added to the mix added to the risk. I needed time to think this over.

"Soma," Jim said, quietly but intensely, "look at me. Do you trust me?"

Slowly, I raised my head and stared into his eyes. I knew he could see my fear: the fear that had always stopped me from taking a chance on things; the fear that I would slip up and ruin everything; the fear that I would sink too deeply into the abyss to return; the fear that overwhelmed me...

...would I let it overwhelm me again? I knew if I walked away from this, I'd probably never have another opportunity. As I continued to look at him, I could see in his eyes the acknowledgment of my fear and a look that told me he would take care of me. And if he trusted these men enough to be his friends, I knew I could trust them as well. I sighed.

"Yes, Sir, I'll do what you wish. You and your friends may have your way with me."

"Thank you, Soma. I know this is a lot to process, and I promise to take care of you. My friends are going to have so much fun with their new plaything."

I needed that bit of mood lightening. "You really know how to get a man horny, Sir. I'm going to ruin my pants."

"Speaking of pants, where are your underpants?"

"I had almost forgotten. They're in my pants pocket."

"Take them out and give them to me."

I did so. And in that moment, I knew I was irrevocably committed to seeing this through and Jim was thoroughly in control. I could relax now.

He handed me a black sleep mask and I put it on, slipping into that special place I go when submissive mode starts to kick in. After a minute, he pulled out of the parking lot and started driving. I was committed to whatever lay ahead. My cock was at full staff and I knew the tissue wasn't going to be able to soak up all the precum. I sure hoped he was going to buy me some panties soon.

I jumped when I felt his hand on my thigh. He stroked me gently and reassuringly, careful not to move too far up my thigh. In the past, his hand would have been firmly on my crotch, squeezing my cock, but this was a different feeling, one that I needed. I slid my hand over to his leg and felt his hardness. In the uncertainty of what was to come, that hard cock was a promise of pleasure.

And then a sharp turn, the sound of gravel and the car stopped. He removed the mask and I blinked my eyes open to see we were in front of an adult boutique. I didn't recognize the store, but it had that couples friendly air of a high end sex shop. I adjusted myself as best I could and we got of the car. I slouched slightly while my erection took its time becoming less prominent. My nervousness had returned with a vengeance. We were in public. All it would take would be one coworker, one family friend to wander by and I would be toast. No doubt the same was true for Jim. He held the door open and we walked in.

The store was well-lit and larger than the usual establishment of its ilk. At the counter, a woman who appeared to be in her early 20s was ringing up what looked like a vibrator for a woman in her 40s. They both glanced our way as the bell over the door rang. The customer turned back to the counter. The saleslady gave us a smile.

"I'll be with you in just a moment," she said cheerfully. I blushed and tried to look nonchalant and maintain social distancing from Jim.

"Take your time," he said, a little too loudly for my taste, "We're just going to pick out a couple of things."

"Soma," he said cheerfully, "let's take a look at the lingerie. I'm sure you can find something nice for your...wife."

Hoping against hope people actually bought that, I walked over (carefully) to the lingerie section, which was less sleazy than most. I tried not to drool too much over some of the sexier teddies, even as I wondered what they carried in my size, and if they would be typically overpriced. But oh, that pair of panties! Was that a chain connecting the two panels? I wondered if they had one in my size and made a note to check this place out again later.

"Look at these," Jim interrupted my dreaming, in a voice that made me realize I'd have to stand much closer to him to avoid complete humiliation. "Aren't these sexy stockings?"

He held up a set of black fishnet stockings, with a tight, tiny pattern and an elastic band and strips holding them together like a one piece garter belt and stocking set. "Don't you think these would look great?" He added, without specifying on whom they'd look great. Given the nature of our shopping trip, I knew who would be wearing them.

"Yes, Sir, they look very nice," I said softly, but not softly enough for the saleslady, who had finished with her customer and was walking up behind me to help out. She looked at Jim, then at my reddening face, and smiled.

"I think those would look perfect on...his wife," she said, looking at Jim and making it clear she understood the situation. "And they're one size fits most, so you shouldn't have a problem regardless of body size." Translation: they'll fit his dad bod just fine.

"I think you're right, Miss," Jim replied. "We'll take those. And I have one more thing I need to get, but first, could I ask a favor?"

"Of course, Sir. We aim to please."

"While I'm picking up the final items, would you mind if he tries these on in your fitting room? I'd like him to wear them now. You can go ahead and ring it up while he's putting them on and I'll pay."

She opened the package easily and handed me the pantyhose.

"The fitting room is over there, Sir," she said, pointing to the far corner of the store. "Wait over there and I'll get the key."

I started to bundle them up in a tight ball, but Jim stopped me. "That's no way to treat stockings, especially when they're a gift," he admonished. "Now, shake them out and fold them neatly."

The three other customers in the store had turned at his voice and watched as I straightened them out. Looking around, I realized that everyone there had figured out what was going on: they had me pegged as a sissy boy, no, a sad old queen. But I also realized something else: none of them knew me and it didn't really matter what they thought. Might as well brazen it out.

I folded the stocking over my arm, held it to my chest and walked slowly to the dressing room door. I turned and looked at them. One thirtyish woman gave me a disapproving stare. I smiled at her and rubbed the fabric against my cheek with a look of ecstasy. She turned away in a huff; the saleslady gave me a small thumbs up from the counter, where she was fetching the key. She unlocked the door and opened it for me.

"Take all the time you need, honey," she said. "I'll make sure your man gets what he wants."

"Your man." Ridiculous...wasn't it? I couldn't figure out whether to die of shame or burst out laughing, so I did neither. Instead, I took off my shoes, socks and pants and sat on the bench to roll on the stockings.

I had worn fishnets in the past, but not a set like this. I worked them up my legs slowly, being more careful since there was no panty for support. When I finally got them on, I couldn't help running my hands up and down them. While not the same smoothness as regular stockings, the mesh felt like a hundred fingers massaging my legs. Oops...time to start taking large square roots in my head so I could get my pants back on.

A knock on the door broke my reverie.

"I have one more thing for you to wear," Jim said, with a smirk in his voice. "Give me your socks. I'll put them in the bag. You won't need them now."

I cracked the door and stuck my hand out the door, not daring to be seen. He took the socks and handed me a bag. "You know what to do," he said.

I closed the door and looked in the bag. He must be kidding! And he bought this in front of that young lady? What will she think of him? Of me? Of us? This is going to be a wonderful afternoon!

I pulled out a medium size butt plug (pink), a condom, a small bottle of lube and two sanitary wipes. The butt plug was heavier than what I had worn in the [dim] past. It wasn't as long as others I had worn, but was just as thick at its widest point and had a longer stem than I remembered, with a curved flange that would fit snugly against my ass.

"I don't want to rush you, honey, but there's another customer who wants to try on some things. Don't worry; I'll stand guard here so no one interrupts you."

Great...that's just what I needed. Wait a minute...you don't suppose she was the one who handed me the bag? Would Jim be that mean? Of course he would...and, apparently, my cock was enjoying the situation. I licked off the accumulating precum and got to work. Speaking of work, I was now so thankful that I had taken that long trip to the bathroom this morning.

After using one of the wipes to sanitize the butt plug, I tore off the top of the condom wrapper and rolled it on the plug, which Jim had thoughtfully taken out of its packaging for me. Then came the lube: lots of lube on the condom, followed by a good coating on my ass. I pushed my finger in to the first knuckle to spread the lube out, then cleaned it on the tissue that had been wrapped around my finger. I was thankful it came out clean, even though it had a funk.

I gave some thought to how best to insert the plug and decided to lean over slightly. I slid it over my ass crack until I found the entrance and pushed it gently. The old familiar sting returned, as well as the discomfort of having something spreading its way in the tight sphincter. I pushed slowly but steadily, tilting it when it met resistance. The pain was growing as I was stretched; I stifled a grunt, but not enough, as I heard a giggle from outside the door. I pushed hard in frustration and embarrassment and, with a sudden relaxation, it was in.

I felt the old sensations of a low level stinging, throbbing pain, along with the satisfaction of being filled,. I pushed the plug in until the flange was flush against my ass crack and just below my buttocks. It couldn't be seen once my pants were on. I repeated that to myself several times, hoping I would believe it. I cleaned up the excess lube with the tissue (I really wouldn't want to try to explain THAT sort of stain). Just to be safe, I took a tissue out of my pants pocket and placed it over my ass, using the garter straps to keep it loosely in place.

Next came the khakis. I shivered with pleasure as the fabric rubbed against my stockings. I wasn't sure how to arrange my cock, as it wasn't in a condition to be tucked, and I didn't have time to wait. I pulled it up and over into one of the garters and hoped it would stay there for a while. I zipped up (carefully) and tightened my belt. After putting everything else in the bag, I turned the knob and opened the door.

Standing there were the saleslady, with a huge grin on her face, a college coed with a teddy on a hangar, and, standing back with his arms folded and a smirk, was Jim. The coed looked inside the changing room, saw that it was clean, went in and closed the door.

"I hope they fit all right," said the saleslady.

"Yes, Ma'am, they fit just fine, thank you."

"Show her how they look on you, Soma. Slip off your shoe and pull up your pants leg."

I hadn't seen this side of Jim before. I knew he was strong willed, but this dominant side of him was new. I liked it, and my inner helpless maiden was ecstatic. I lowered my head, slipped off one shoe and pulled up my pants leg to my knee. On an impulse, I raised my heel and twisted my foot in a vamp pose.