The Shopping Spree

Not for the first time, I was glad to be blindfolded. As I expected, Pete was not going to allow me dress until we arrived at the next stop. At least, he had enough pity on me to keep the vibrator turned off on the butt plug that felt like it had taken up permanent residence in my ass. Had his windows not been tinted, a passing driver would have been treated to the sight of a blindfolded man wearing a polo shirt, a blue thong with embossed rose and a pair of black fishnet crotchless pantyhose that looked like they were sewn to garters.

"Don't be shy, darlin'. Keep those legs spread out so I can admire the view."

I didn't know where we were going, but I hoped it would be a short drive. He kept one hand in my lap, seemingly entranced by my panties. He was rubbing the gusset and squeezing my cock, which was responding with more and more precum. I was growing desperate to cum, but I knew I wasn't going to be given release today. The gusset did little to keep my precum from seeping through. I wondered how I was going to avoid stains on my khakis when I put them back on.

"You're getting precum on my fingers, Soma. We can't have sticky fingers on the steering wheel. Open up."

I opened my mouth and he stuck his fingers in it. Without having to be told (I didn't want to give him an excuse to turn that damnable vibrator back on), I sucked and licked my precum off his fingers, treating them like a cock. The sweetness of my precum mixed with the salt of his fingers to make me even hornier, which resulted in more precum.

It was a vicious circle that got my cock twitching dangerously. I could feel the head starting to poke out of the top of the panties. He started teasing my cock head, running a finger around it and rimming the underside of the head with his thumb.

"Sir, please...you're going to make me cum if you don't stop." My confident voice had gone: I was almost a soprano as I pleaded desperately for him to stop. My thighs had started to shake.

"That wouldn't be smart, Soma. You wouldn't want to cum all over your shirt, would you? I'm sure the people who see you would find that an interesting fashion statement. Maybe you need a little extra distraction?"

"No, Sir! Please don't turn on the vibrator! I won't last 10 seconds if you do."

He moved his hand away from my crotch. I could hear him fumbling for something and knew I only had seconds to avert a cum catastrophe.

"Sir, I would never want to displease you and I fear if I cum now, it will go all over your car. I don't want to soil your seats or your carpet. Please, Sir, don't let me mess up your car."

"Hmm...that's a valid point, Soma. I don't want my car messed up. And besides, you're so cute when you're groveling," he added, not unkindly.

I wanted to grab my cock and jack off in his direction. As horny as I was, it wouldn't have taken long and I was sure I'd get it on his clothes. The insufferable little prick...

...the insufferable little prick who had just given me one of the top ten loads of my cocksucking life, who had masterfully used my mouth...yes, he was a jerk, but he was one of Jim's friends and I had promised to do what they said today. Besides, I sensed he was, deep down, a decent guy, with a nasty sense of humor, something with which I could relate. I was sure he was having a lot of fun watching me panic. Rather than growing angrier, that thought cooled me down. After all, I was here to serve them this afternoon in exchange for a bellyful of cum, and Pete had certainly delivered on his end.

"Thank you, Sir. May I ask you something?"

"Sure, darlin'."

"When we stop, could you get my cock shriveled again? I don't trust myself to touch it, as sensitive as it is."

I heard him shake a cup. "Yep, there's plenty of ice left in there. No problem, darlin'. I want to deliver you to George in good shape, so he can have his fun. He's not as experienced as the rest of us, so treat him nicely and show him a real good time."

"Of course, Sir. I'm here to please and I want to make sure he has a great experience."

"That's the spirit, darlin'! And we're here. Pull your panties down."

We stopped and I unbuckled, pulled my panties down and squealed as Pete pressed a bag filled with ice to my cock. He laughed as I squirmed, but the ice did its work: my cock was soon shriveled to a nub. He dropped a napkin on my lap.

"Dry yourself and get ready to meet George."

"Yes, Sir. Where are my pants?"

"I'll get them for you."

I heard his door open and close while I dried myself and pulled up my new blue panties. I straightened out the thong that was buried in my ass crack and waited. I knew better than to take off the blindfold until Pete told me. After a couple of minutes, my door opened and a cold breeze blew over my legs.

"Hop out, Soma. I've got your pants here."

"But Sir, what if someone sees....ooooh! Please, Sir, not the vibrator! I'm getting out!"

I stepped out of the car quickly, hoping he would turn off the butt plug before I needed another ice treatment. Thankfully, he turned it off as soon as I was out of the car and standing. He pulled off my blindfold and I saw we were in a distant corner of a Costco parking lot. He had the rear door open, shielding me from view. The wind blew, raising goose bumps on my legs. It was freezing out and I was still without pants, jacket or shoes. My toes were freezing.

"I'm disappointed, Soma. I told you I would take care of you. You're going to have to learn to trust me...to trust all of us."

"I'm sorry, Sir. I should have known better. Of course, I trust you."

"We shall see. Meantime, meet George. I wanted him to see how cute you look in your panties and stockings and to give him some shopping ideas."

"Hello, Soma."

The voice belonged to a man who seemed to be in his late 30s. He was a little taller than me, about 5'10" and in good shape. He sported a nerdy look, complete with black horn rim glasses. He was wearing an open neck light blue dress shirt and grey khakis. He stared at my lower body, especially my thong.

"Hello, Sir. I hope you like what you see."

"Very much, Soma. I haven't seen a crossdresser before...I mean, in person. I've seen plenty online, of course...not that I spend all my time looking at crossdressers online..."

"Slow down, George," Pete said. "We all know why we're here; you don't need to explain yourself. Soma here is a nice guy and he really wants to make you feel good. Don't you, Soma?"

"Absolutely, Sir. I'm grateful to you for taking me shopping, and I hope to show you just how much I am after our trip."

"Um, yes...so am I. But, Pete, shouldn't he get his pants on? Someone might see him."

Hmm...he seemed more nervous than I was. And he was a youngster compared to the rest of us. I recalled my high libido and short refractory time when I was his age and licked my lips. This was going to be interesting, and tasty.

"Don't get your panties in a wad, George. Soma isn't, are you? See? But I'm glad you said that. Soma here is a pretty horny guy and gets erect at the drop of a hat. We wouldn't want him to embarrass you in the store, so why don't you tuck yourself, darlin'?"

"Yes, Sir." I reached inside my panties and pulled my cock between my legs. I pulled the thong out enough to stretch my cock and place the head between my ass cheeks. Next, I pushed my testicles back into my body, then pulled the panties up as high as they would go. I hoped that would keep me in check for the moment. George had his eyes glued on me during my impromptu tucking...well, he had his eyes on my panties and what lay beneath.

Pete handed me my pants and I pulled them on quickly. After fastening the belt, I reached into the car and retrieved my shoes. Pete gave me my jacket and I put it on gratefully.

"Here you go, George. He's all yours. Take good care of him. If he gets out of line, you know what to do. See you later" The look he gave me told me exactly what he meant, and the speed with which I shook my head told him I understood. He got in his car and pulled out. George and I were alone in the parking lot.

We started walking toward the entrance. George seemed nervous and avoided looking at me, striding quickly ahead. I struggled to keep up; the plug seemed to bounce up and down and increased my discomfort.

"Please, Sir, could you slow down? My bum is starting to hurt."

He stopped abruptly and turned around.

"I'm sorry, Soma. This isn't quite what I expected. I'm not sure I'm ready for this."

"Sir, am I displeasing you?"

"No, and, please stop calling me Sir...my name is George. There's nothing at all wrong with you. It's me: I'm not experienced like the rest of them. Jim told me about this and I wanted in, but it's all so different than what I thought. I'm not sure what I'm doing here."

"I understand, Si..George. It was all a bit overwhelming for me at first. Would you like to talk about it before we go further?"

"I think I need to, Soma. But where can we go that's private?"

"Is there somewhere nearby we can get some coffee?"

"There's a Starbucks just down the road, but the tables are too close together to talk."

I realized I was going to have to make the ultimate sacrifice and drink the worst coffee in the universe. But I had been in George's position...to some degree, I was in it now. I remembered how nervous I was the first dozen or so times I played with men. I wanted to take care of him and help him fulfill this fantasy.

"We could hit the drive-thru and bring it back here. We can sit in your car and talk for as long as you want. And if you still feel uncomfortable about doing this, we don't have to."

"Thanks, Soma. That sounds like a plan. My van is over there." We changed direction and made our way, shivering, to his van. He opened the passenger door for me.

"Get out of the cold. I'm going to give Jim a call."

I got in the car and looked around. While clean, it was definitely lived in. There was a car seat in the back and I started to understand things. My musings were interrupted by the driver's side door opening and George climbing in. He handed me the phone.

"Jim would like to speak with you."

"Hello, Sir. This is Soma."

"Can George hear you?"

"Yes, Sir."

"We need to talk privately."

"Just a moment, Sir." I opened the door and stepped out into the wind. I gave George an encouraging smile and closed the door. I had his phone, so I didn't have to worry about him running off without me.

"Soma, I've been talking to George. It sounds like he's getting cold feet."

"Given the weather, Sir, I'm not surprised. My feet aren't the only things that are cold out here."

"Ha, ha. Seriously, I think I need to come and pick you up."

"Sir, I wish you wouldn't. I think George wants this. He just needs some encouragement. Let me talk to him."

"I know George a lot better than you do, Soma. I don't think that's going to matter. Besides, we're getting behind schedule."

"Yes, Sir, I understand. May I ask why you asked George to be a part of this group?"

"Because he's been wanting to get his cock sucked for ages and his wife won't touch it with her mouth. She says it's dirty."

"Ouch! Been there, heard that. What about the clothes? Is he into men wearing lingerie?"

"He's watched his share of tranny porn and talks about it a lot."

"I'm not exactly Natalie Mars, Sir."

"No, but his wife is very conservative sexually and doesn't like to dress up for him, so I thought he would enjoy having you do so. He wants a cocksucker, that's for sure, but I don't think he's ready for it yet."

"With respect, Sir, it sounds like if he doesn't do it now, he never will, and he'll be miserable and wind up doing something stupid with a hooker."

"I don't disagree with you, Soma, but he said he doesn't want to continue."

"Let me talk to him, Sir. We're going to get some coffee and talk in his car. Give me 20 minutes. If he still doesn't want to go ahead, no problem. But I'd really like to get a taste of his cock. You asked me to trust you, Sir. I'm asking you to trust me."

"It's your tail freezing out there, Soma. OK, I'll let the others know there's a slight delay. But we're on a fairly tight schedule: you need to be finished shopping there and on your way to the next spot in an hour."

"I understand. Thank you, Sir. I'll give the phone back to George. One more thing, Sir..."

"Yes?"

"Please don't tell the others about George. The last thing he needs is for them to tease him about this."

"You're a good man, Soma. I think we chose well. Give the phone back to George."

I reentered the car, grateful that George had seat heaters and had kept it running. I handed him the phone and waited. I rubbed my tush on the seat, not only to get warm, but to push the plug in a little more. Its pressure and dull pain provided me reassurance that I was doing the right thing.

"Yeah, Pete? I don't know that I'm going to change my mind...I just don't know...OK, I'll talk with him...I'm sorry about this, Pete, I know I'm letting you and the guys down...thanks....yeah, I'll call you if you need to pick him up. Thanks...bye.

"OK, Soma, let's get some coffee and talk. I don't know that it will matter..."

"...but it's always best to make a decision based on sufficient data," I completed, hoping I had guessed correctly about his nerdiness.

"Exactly," he said, looking at me more closely.

"I keep my pocket protector at home," I told him with a smile. "We nerds have to take care of each other. Now, about that coffee...I'm freezing."

We went through the Starbucks drive-thru. He had a latte; I had a cup of mint tea. By the time we returned to Costco, they were cool enough to drink. I looked at him, but he wouldn't maintain eye contact. I could see I was going to have to take the initiative.

"So, George, you're having second thoughts? Is it something I've said or done?"

"Not at all, Soma. And, by the way, where did you come up with that? Surely that's not your real name."

"No, it's not, and stop calling me Shirley." He laughed at that and I smiled. Not only had he caught the reference, he was relaxing a bit, perhaps starting to realize I was an actual human being.

"Actually, it's a literary reference. You'd be surprised how many people think I based it on the lingerie store."

"A literary reference.....wait a minute: Brave New World?"

"I'm impressed, George. You nailed it first time. I hope I have the same effect on people as the drug did in that book."

"Keep them mindless slaves of the social order?"

"No, enhance their pleasure and bring them to new heights of joy. If anyone's the slave, it's me, not them, and I'm hardly mindless."

"I can tell that. Tell me, Soma, if it's not too personal, why are you doing this?"

"Because Jim is giving me an opportunity to fulfill a long standing fantasy of mine, to pleasure a group of men orally. Given the world today, I figured I'd never be able to do that, what with all the STDs going around. However, I've been playing with Jim for a while and trust him. If he's vouches for you guys, that's good enough for me. Besides, he's got a yummy cock and, as best I can tell so far, so do his friends."

"Are you married?"

"Yes, and, to answer your next question, no, she doesn't know what I do, nor do I intend to let her know. While I enjoy my explorations immensely, I try always to make sure my big head is the one doing the thinking."

"You don't feel bad about cheating on her?"

This was the critical question. I knew he was projecting that question onto me. He was trying to justify this excursion.

"I've thought a lot about that over the years, George. Here's the situation: after many years of marriage, the urges and desires I've suppressed had started bubbling to the surface. I had been taught from youth that the needs I could feel inside were bad and abnormal. For years, no, for decades, I've built walls inside me to keep them at bay.

"However, the walls started crumbing several years ago. I did some playing on business trips, first with call girls. Besides being expensive, I found them to be oddly unsatisfying. The only sexual aspect I really enjoyed was when they went down on me, but watching them spit out my cum after I ejaculated really took the fun out of it. And there was the guilt of cheating on my wife while she was taking care of my daughter." That last detail was in response to the car seat in his van.

"Then, remembering the fun I had with self-bondage in my teen years, I hooked up with a couple of female Dommes. That was much more fulfilling, and I discovered I had a much greater pain tolerance than I had suspected. I also discovered how much I enjoyed submitting to the desire of another person and letting them use my body. Actually, it was more than a desire: it was a need.

"Sadly, I also discovered that there was a strong emotional component at work. I found myself falling in love with more than one of the women I served. And I couldn't allow that to happen: whatever else, I was committed to remaining with my wife and taking care of her. If I had to stop my explorations and remain sexually frustrated the rest of my life, that was a price I was willing to pay.

"And then, I made a trip to Pegasus that changed my life."

"Pegasus? What's that?" It was clear George hadn't done much research on gay sex in the area, or he would have heard of it. And it clicked: this was probably his first bisexual experience. If so, I had an idea on how to proceed.

"It's an ABS, an Adult Book Store, in the area. It's a place people, mostly men, go to watch bad porn and try to hook up with other guys. It even has glory holes.

"Anyway, growing up, any hint of male-male sexual contact was taboo, an abomination. Even though submitting to men was becoming more a part of my fantasy life, I hadn't taken the next step. And then, I had an afternoon unexpectedly free and decided to take look at the place. I had read about it online and knew it had an arcade section that showed all kinds of porn. I was feeling horny and figured I could watch some porn and get some relief. But I don't want to take too long...

"That day, while watching porn in a booth, a cock came through a hole in the wall. I was frozen, then, emboldened by the anonymity, I touched it. I saw a drop of liquid on the tip and I licked it. That one taste was a combination aphrodisiac and pheromone hit. I took that cock in my mouth, milked it dry, and haven't looked back."

"Wow! So you found out you were gay?"

"No, George, I wasn't gay. I'm still not, as far as I know. (

Who am I kidding? I'm rationalizing. When will I be ready to admit the truth to myself?

). I was addicted to the cock, not to the man behind it. For me, it's all about the cock and cum.

"I thought the taste of cum would have made me throw up, and I still don't like it when it's not coming straight from a cock in my mouth. And over time, I've learned that it's not the cum itself: it's that I'm being fed cum by a man to whom I've brought pleasure. The cum is his reward to me for submitting my mouth and body to him."

"But you like to wear women's clothing. Are you trans?"

"No. I enjoy wearing women's clothing, but not because I want to become one. Apart from the logistics, I'd never be anything close to passable. I enjoy the sensual feeling of the clothes on my skin. And, for me, submission and femininity are intertwined. I'm not trying to be sexist. It's just that I've found inside me is what I call my 'inner helpless maiden,' who expresses herself in submission and feminine attire.

"I'm afraid I'm not doing a very good job of explaining it," I apologized, though I could see that George's cock, at least, was interested in the story. "There's not an easy answer to your question, because I still haven't figured out exactly who I am. But my explorations are helping me find out, and what we're doing today is turning into something very special in my journey.