The Shopping Spree Pt. 03

"I want you to know this, George. If you buy me some item of women's clothing and I wear it for you, you're not a tranny lover.

"If I suck your cock and swallow your cum, you're not gay.

"If you enjoy the experience, that's great: you've learned something about yourself safely. Jim and his friends aren't going to say anything to anyone and neither am I.

"If you don't enjoy the experience, that's OK: you've still learned something about yourself, safely. And I can tell you this from experience, George: if you don't satisfy your cravings, one of two things will happen: you'll go through life frustrated and miserable; if you do that, whether you want it to or not, it will affect your relationship with your wife. Or you'll wind up overwhelmed with lust one day and do something stupid that will wipe out your health and, possibly, your marriage. Nobody wants that to happen to you.

"But I've talked too much. It's your choice to make, and whatever your choice is, no one will think any the less of you. So, George, what'll it be? Want to go shopping?"

I had said what I could. If he still decided not to go through with it, I would be disappointed, but he had to make the right decision for himself. And if he did bail, well, that wouldn't be the first time a guy had ghosted me. I sipped on my tea and waited. At least, the tea was keeping me warm and freshening my cum breath.

After what seemed like hours, he turned to me with a questioning look. "You're right," he sighed, "I have to get this out of my system one way or the other. Let's go shopping."

"Thank you, Sir. I think Jim would like to know of your decision. I'll wait outside, if you'd like."

"Thank you, Soma. I'll join you shortly."

I got out of the van and stood against it, suddenly shaking, and not with cold. I had revealed more of myself than I ever had to anyone. Was it because I saw myself in George and wanted him not to waste the years in frustrated longing? Was it because my hunger for his cock had overcome my own discretion? Was he going to pull out and leave me stranded here with no wallet or phone? That would be funny...not.

The sound of his door closing told me I wasn't going to have to hitchhike home. He came up with a determined look in his eyes, a man with a plan and ready to implement it.

"Here's what going to happen, Soma. We're going into the store and you're going straight to the women's lingerie aisle. You're going to find a box of bralettes that fit you. You know what bralettes are, don't you? Fine. Make sure one of them is blue, preferably a dark blue, to match your panties. And if you linger too long, I'll remind you of the time, like this."

I jumped as the plug sprang to life. "Please, Sir, I'll be quick. You don't have to goose me with that."

He turned it off and chuckled. "You should have seen the look on your face, Soma. This might be fun after all." Oh, no: had I awakened his inner sadist?

"Let's go, Soma. Time is short." He set off toward the store, with me following close behind. We both had to get in on his membership card. He stopped in the computer section.

"I'm checking out the laptop sales. Bring me back your choice. I turn it on in two minutes. Good shopping."

I sprang into action, walking as quickly as I could without bumping into the shoppers headed toward the food samples. I hoped I hadn't created a monster. More likely, he was enjoying playing with his new toy. When I finally arrived at the women's aisle, my heart was pounding from more than the walk: the prospect of my ass erupting into pleasure/pain with no place to hide whatever happened in my pants filled me with terror/joy. There was no place to hide and no way to avoid the usual crowds.

Where were the boxes of bralettes? There they were: next to the rolls of panties. I pulled one out and checked the sizing, trying to get it right. Hmm...looks like a Large for me. I scanned the boxes for the ones marked with the blue L (how appropriate), then started looking for one that had a blue model inside. Flesh tones....white...red...where were the blue ones? Wait: they're in the same box with the red one. Got it...

...and then my two minutes were up. I squeezed the box in my hand and tried not to jump, succeeding only in almost toppling the carton of bralette boxes before settling down. My cock had been waiting for this and started trying to inch its way into my ass. I took a cleansing breath, ignoring the glances of the shoppers around me. I composed myself and walked back to the computers, struggling to maintain a dignified walk. I arrived at the computers to find myself alone.

Where had George gone? My composure vanished as panic started to set in. Had he chickened out at the last minute? Was he going to leave me in the store with a vibrating plug and no way to contact anyone? I had to find him while I could still walk.

A tap on my shoulder gave me a start. I turned and saw George standing there, with a sheepish grin and an evil glint in his eye.

"I had to hit the restroom, Soma. Did you miss me? I see you found what you were looking for."

"Sir," I hissed, "could you please turn it off?"

"Turn it off? What do you mean....oh, that." And then, blessed relief.

"I did warn you about the time limit, didn't I? When your two minutes was up, I turned it on, and then, I suppose the coffee kicked in and I had to do something about it. Oh well, no harm, no foul, right? Let's go pay for it."

"Sir, I need to hit the men's room, too. May I?"

"You don't need to ask my permission to do that...oh, I guess you do, don't you? Go ahead; I'll check out and meet you at the car. But don't be long. We're on a schedule, you know, and I'd hate leaving you here."

Part of me was glad to see him getting in the spirit of the game; part of me wondered what I had unleashed. All of me headed to the bathroom as quickly as possible. I really did need to empty my bladder.

I walked into the men's room and looked for an empty stall as far from everyone as possible. I went into the stall and unbuckled my pants. Instinctively, I lowered my panties and sat down; a lady does not urinate standing up. My cock sprang up, free of its restraint and I pointed it down carefully so I wouldn't get anything on my stockings. I forced a stream through the semi-erection and sighed. My ass took advantage of the moment of calm to complain about its fullness. I had a feeling removing the plug was not going to be fun.

I was relaxing and enjoying the quiet of the stall, until I realized something: if George started the vibrator before he left the building, I'd never make it to his van without exploding. I wiped my cock head dry, stood up and retucked before pulling up my pants. I washed my hands as quickly as possible, then walked out of the store as quickly as I could without attracting attention.

To my relief, George was waiting just outside the door.

"I thought you might not remember where I parked," he said considerately.

"Thank you, Sir. That was quite an eventful trip."

"I hope I didn't overdo it. I decided to take your advice and immerse myself in this to see how I like it. I might have been a little too enthusiastic."

"You were fine, Sir. And how do you like it so far?"

"I'm surprised how much I like it, Soma. I've never had someone I could use like that. It's a surprisingly sexual feeling for me."

"In what way, Sir?"

"Knowing I had the power to humiliate you in public and that you had willingly given me that power over you. When I turned on the vibrator, I got an erection and had to go to the restroom to adjust myself."

"I hope you didn't masturbate, Sir."

"Oh, no, Soma. That would spoil the main event. Now I really want to feel your lips around my cock."

"As do I, Sir. But remember, I have to put on the bralette first. Those are my orders from Jim."

"I want you to do so, Soma. In fact, I've been giving thought to the logistics. When we get to the van, I want you to get in the back seat, take off your outer clothes and wait for me to join you. I need to call Jim."

We arrived at his van and I entered through the sliding side door. As it closed, I looked around and saw the windows had covers on them to keep the sun out of a baby's face. They provided only partial cover for me, but we were far enough away from the other cars that I should be safe enough.

I pulled my shirt over my head, kicked off my shoes and shimmied out of my pants. After laying them carefully in the front seat, I sat upright with my knees chastely together. I was definitely channeling my inner helpless maiden and sat demurely with my eyes down while George finished his call. My cock was still trapped under the thong and I rocked forward a bit to try to force it more into my ass crack. I was starting to leak precum and I didn't want to stain his seats.

My nipples were growing erect from the cold in the car and I wished that Jim had chosen closed mesh rather than fishnet for my stockings. As small and tight as the mesh was, it didn't help at all in keeping my legs warm. At least my cock was also retreating from the cold.

I ran my hand absently over my nipples, pinching them. I ruffled my chest hair slightly...chest hair. Stomach hair. Dad bod. Middle age spread. Would George be repulsed? Would he laugh at the spectacle of a late (very late) middle aged man wearing lingerie? The other men knew the score. George was new at this. Would his introduction to reality shatter his fantasy?

He opened the front passenger door and climbed in. He opened the box, pulled out the blue bralette and tossed it and the blindfold over his shoulder back to me.

"Tell me when you've got these on," he said. Interesting: he wasn't looking at me until I was fully clothed. He was playing with his phone and seemed troubled. I wondered what had happened on the call with Jim, but he clearly wasn't in the mood to talk.

"Yes, Sir," I replied and pulled the bralette over my head. It wasn't an exact match for the panties, but it was close enough. I pulled it down over my chest. I had guessed right on the size. It was snug, but not tight. I pushed and pulled my skin and got as much into the cup areas as possible. Being a bralette, it wouldn't give me a full figure (thankfully), but the pressure did squeeze me into small man boobs. It covered much of my chest hair, but it was a long way from turning me into a woman. I adjusted the straps and put on the blindfold.

"I'm ready, Sir," I said, hoping my own nervousness wasn't apparent in my voice. I heard him turning; then, nothing. I started my cleansing breaths, not breathing out of my mouth for fear of him misinterpreting it. Then, a sigh from the front seat.

"Soma, get on the floor on your knees."

"Yes, Sir." I worked my way down to my knees, facing the seat. Given the space, that was a bit of a squirm, but I managed. Knowing he would have to sit where I had been, I slid over until I was in front of the car seat. I felt him walk past me and sit down.

"Get between my legs. You know what to do. I hope you're not disappointed." There was a slight tremor in his voice as he spoke the last sentence. I had a feeling this was not the first time he had said it and had a suspicion why. If my hunch was right, I knew just what to do.

I put my hand on his knee for support and slid into position between his legs. I felt up his thighs toward his belt, deliberately avoiding his crotch for the moment. I found his belt and loosened it. I moved my hands along his pants, scouting out the fasteners, and also checking out his package. Apparently, he wasn't erect yet...or my hunch was correct. One way to find out...

I unsnapped the top of his pants and lowered the zipper slowly. George took a deep breath in and lifted his tush from the seat, allowing me to lower his pants to his knees. I straightened up, pushed his knees together and lowered his pants to his ankles. He opened them again and I resumed my work, sliding my hands up his legs. The blindfold enhanced my sense of touch and I noticed he had very fine leg hair and almost no hair on his thighs. All in all, a fine specimen of a man. My hands reached the edge of his underwear and I was surprised to find he was wearing boxers. I had pegged him a briefs guy.

I reached the waistband and pulled it down while burying my head in his crotch and inhaling deeply. I felt a trimmed bush and smooth skin. He smelled of soap with a touch of manly sweat that was not displeasing. And then, his cock...

I was surprised to find it wasn't erect yet. I wasn't surprised to find it to be no more than three inches long. I knew then my hunch was correct. He verified it.

"I guess you were expecting something a little bigger, weren't you?" I could hear the bitterness in his voice.

"Sir, you have the perfect cock for my mouth. I love feeling a cock grow in my mouth and fill it without choking me. Contrary to what you may have seen, most cocksuckers really don't like having their throats ransacked. Just sit back, Sir, and let me enjoy your cock."

I put my hands behind my back and sucked his cock in my mouth. This was going to be a hands free blow job that would, I hoped, rock his world and show him how special his cock was. I explored it thoroughly with my tongue, wetting it down and feeling it start to expand. I sucked gently and continued to move my tongue over the shaft and around the head, not wanting to start bobbing until it was stiffer.

When it stopped growing, I was pleased to discover it barely went toward my throat. I was able to hold it completely in my mouth with ease. I lifted my head slightly so I could survey it with my tongue more completely. The shaft was smooth, with only the central vein under the shaft visible to my tongue. I pulled up and felt his cock head start to slide over my tongue, as I prepared to go to work in earnest...

...but stopped as I heard him cry, "No, no, no," and felt his cock pulse. My mouth filled with a warm, thick, sweet liquid. I swallowed in surprise, as his sudden eruption had caught me unprepared. It was a tasty load, and I loved it, but his cry was not one of pleasure. And now the picture was complete. He was dealing with premature ejaculation. I had already been concerned about how he would handle post-orgasm guilt. He was now starting to feel frustration and shame at his speedy completion. I knew I had to act rapidly.

"I'm sorry. I'm sorry," he repeated.

I kept sucking on his cock, pulling out all his cum. He was still erect, which gave me a glimmer of hope. I coated his cock in saliva and pulled my head off it. I started stroking his shaft with my hand, making sure to rub the underside of his cock head and keep it erect.

"Don't be sorry, Sir. That was incredibly tasty. And I'm going to show you just how much I enjoyed it. Whatever you feel, ride it through. We've only just begun." And I dived back onto his cock.

Many years ago, a Domme had shown me the ultimate in orgasmic pleasure/pain. It was time for me to pay it forward. I sucked in my cheeks hard and sealed his cock in my mouth. Then, I started bobbing furiously, flattening my tongue against his cock. He started twitching: I heard him panting, then moaning. I knew his cock was super sensitive at this point. In a moment, the pleasure was going to turn into something else.

"Soma, please stop. You're hurting me." He tried to pull my head away, but I grabbed his wrists and kept on pumping. He was trembling now and bucking his hips, which only pushed his cock deeper into my mouth. I felt the precum flowing freely now and redoubled my efforts. If this was going work, it would be soon...

...and soon it was. My mouth flooded with a gush of thick, sweet liquid that flowed like he was urinating in my mouth. I knew from that past experience that it wasn't urine. I focused on swallowing as quickly as I could. There were three intense, prolonged pulses. I had stopped bobbing when the flow started, and now I had to move my head off his shaft to allow the liquid to fill my mouth.

George was almost screaming in pain and pleasure. "Oh God, oh God, oh God, oh God..." His hands were around my head, squeezing it tight and driving my mouth down on his cock. I focused on timing my breathing with swallowing the massive stream, lest I choke on it.

And then it was over. He leaned back, wheezing. I slid my mouth off his cock slowly and took off the blindfold to see if he was OK.

"Sir? Are you all right?"

"Oh...my...God...what...was...that?"

"It was a trick a Domme showed me many years ago. She did that to me while I was tied down. I thought I was going to go through the roof."

"I didn't mean to pee in your mouth, Soma. I'm sorry."

I chuckled. "That wasn't urine, Sir. As best I can tell, it's pure seminal fluid. Trust me, it didn't taste like urine. It's actually quite tasty. I hope you enjoyed it."

"I think I did. I've never felt anything like that in my life. It was almost an out of body experience."

"I know, Sir. I wonder if that's what it's like when a woman squirts? Anyway, thank you, Sir, for letting me enjoy your cock and cum and thank you for letting me share in this very special experience."

"Wow...I'm going to be processing this for a while. All I can say is, thank you, thank you, thank you, Soma. You have no idea what this means to me."

He was wrong. I knew exactly what this meant to him. He had had a taste of the joys of exploration and he wasn't going to stop. I stroked his thigh gently as he lay back, eyes closed and still breathing heavily. I remembered the day when I had been in his position: so did my cock. Where would his journey take him? I had no idea, but I smiled, knowing I had started him on it.

To be continued