A Boyfriend Shirt Tale

That's why it wasn't a huge stretch for me to become Lois's 'webmaster.' In terms of what else I did, I technically also became a pornographer, because I operated the camera that took the video of my girlfriend's salacious activities. Did keeping this a closed two-person shop really make it safe? Unlike at work, if I saw something that threatened Shirley Shares Your Shirt! I couldn't alert an in-house cybersecurity pro. I'd be all by my lonesome.

Yes, that's the title of the show. We're both familiar with the old movie Airplane! and how it started a second, comedic career for Leslie Nielsen. Lois and I go out of our way to say 'surely' plus something, so the other can reply, with a finish of 'and don't call me Shirley.'

I already had some useful equipment. A ring-light, which I used in my Zoom calls. It fit well around a decent digital vidcam, more capable than a fixed webcam or a phone. A tripod, and a microphone cushioned to block stray noise. We put a blank backdrop behind Lois's bed, tall and wide enough to hide her bedroom walls from all angles.

When I say 'we,' I mean mainly 'she,' as far as what she would do and how she wanted it to look.

Before she committed to anything, we set everything up in her bedroom to run a rehearsal. I took video so she could see it afterward.

"Hi, I'm Shirley," she said, sitting on the end of the bed. "Today I'm going to wear your shirt." She delivered this in a sort of cooing voice, and unzipped her plain gray hoodie slowly. She looked at the camera, not very expressively because of the mask.

"Um, the shirt's right here," she said, pointing to her right. She stood, shucking off the hoodie, then pulled down the dark blue yoga pants.

Her focus strayed from the camera. I forced myself not to give notes, she'd see the video herself later.

"It's like you're my boyfriend," she said while reaching back to unhook her bra. Her voice wasn't even remotely sexy. "That's what I'd do when we're together, take your shirt, and wear it." Her posture was slack, nothing to indicate excitement, or even interest.

She dropped the bra and looked straight at me. "I'm not feeling it."

"You could write a script," I said, now that the rehearsal had stopped. "I could put it on cue cards--"

"It's not that," she said. "Every time I've thought about this, it's either just a few seconds when it amuses me, or while you and I are making out. If I'm just doing this on my own, the sizzle doesn't last."

We looked at each other, likely with the same idea at the same time.

The left-side smile showed just below the bottom of the mask. She said, "I need a fluffer."

The wig and mask still did nothing for me, but her breasts were already out and about.

We rolled around on the bed, mostly just groping, because the mask made kissing problematic. She still got to heavy breathing pretty quickly. "Not too much," she said. "Just a little more." Then, with both of us starting to get humid, she said, "And your shirt!"

She got it off of me, then pushed me away. "Back to work!"

I hobbled behind the camera. By the time I had restarted video, she had dressed again, and tossed her thrift-store shirt out of sight.

"Hi there, Mister Sixty-Nine Dinosaur Dong," she said, her look intense even through the mask. "We can't be together tonight, but we can still make each other happy. I love to wear my boyfriend's shirt, and he loves to get it back from me, after I've had fun with it!"

She kept up a good palaver through her strip, her donning of my shirt, and a lot of rolling and rubbing of her luscious lady self on the overwhelmed cotton-poly blend. She made up plenty of detail about the man who had sent her this gift, describing how various parts of him looked, felt, and smelled, including inside the shirt. This was the sort of data she'd request from her clients.

Her last action was bringing her fingers from behind on the front tails. I got a close up as the tails vanished between her labia.

"Thank you, Dino Dong!" she said at the camera, stripping the shirt. "Playing with your shirt made me feel so good! I know it'll do the same for you!" She tossed it at the camera, where it covered the lens and stayed there.

"Turn it off!" she bellowed. "Condom! Now!"

I turned the cam and ring-light off, pointed the tripod far away, and dove to the bed. The wig hit me in the face.

I had the condom ready, but we found ourselves first in a tight embrace, rolling around. "I want to feel you!" She panted. She slapped my butt and nipped at my ear. "Like that!"

We'd never been rough with each other, and I'd never done that with anyone. I was fully erect, and had been since late in the video, but now I had no clue. I tried a few love bites, nothing that would cause a hickey, and squeezed her breasts (nothing new, by me to her). Then I did indeed smack her bottom a few times. Flat-hand spanking of the human posterior, which is well cushioned--especially mine and Lois's--can produce plenty of sound and sensation without causing damage. I still worried about hurting her, and was relieved when she got us upright, saying, "Get that rubber on, and in!"

I don't know what made her think of this position. She had me stand on the floor while she put her right knee and left foot on the end of the bed, and pulled her left thigh towards her. This made my entry sideways, sort of. I sucked in my gut, but I may not have needed to, because this arrangement was not impeded by our excess flesh.

Her look over her shoulder at me was intense, but somehow also blissful. "Thanks for humoring me," she said. "Something else I was curious about. Rough treatment doesn't have to be a keeper."

"Glad to hear it," I wheezed, swelling and heating, ready to blast, this felt so good!

"I'll take Rob Dong," she quick-spoke, "over Dino, Daaaaaaahhhh!"

I got both arms around her midsection to keep her from collapsing. She ground her trunk at me, I rammed deep and deeper. We both seemed to vibrate. I think that's what happened. If I hadn't turned off the cam, I could check to make sure.

In a while, we were calmer, and very happy.

We were trading tiny, tender kisses, enjoying relief and accepting exhaustion, when she said, "Does this cure your shirt envy? You're my before and after. Nobody else will ever know that."

Sometimes, during her cam career, the before and after weren't that smooth. But there were always some upsides for us.

***

The rehearsal video became her audition piece. The same day she sent it, the platform sent back a participation agreement.

Her first video was a promo that her platform copied to a free porn site. Lois was just as steamy in this one, while introducing 'Shirley' to the world, explaining what her VIP fans could do, and then demonstrating what she does to her boyfriend's shirt.

This was yet another thrift store shirt. I had bought it. It was my size. I wore it before she used it. I would never wear this shirt in any other part of my life. So far, we were staying ahead of the curve on privacy. I hoped.

Lois was nervous as we waited for the video to go live, a few nights later. "The platform is being very helpful, trying to declare its policy that any body type can be sexy," she said, "but a lot will depend on how many views this gets, and its rating from the thousands of general-interest, and cheap, viewers on a free site."

"Everything else is ready," I said, my arm around her shoulder. Her cat was in her lap. Because of confidentiality, this was the limit to her support group. "From your home page, or the end of this video, a guy feeds to the QR code to pay for shipping both ways, and his one-time VIP membership. I reactivated a rental mailbox at a ShipCo store, under my old online auction account, very hard for an outsider to trace to me."

She nodded as we stared at the laptop on the coffee table. "We've spent everything we have to, if this goes no further," she said. "The platform has me only on time-delay. Live streaming would cost a lot more." She turned a serious expression to me. "Does it bother you that I'm acting like a slut?"

I think she intended to throw that into our nuts-and-bolts conversation, to get me off guard. It worked, a little. But only to the point of me looking surprised. "We had this conversation a long time ago."

"But now it's really happening. I'm showing my tits, ass, and pussy to the world, and acting out some weird fetish. Think about that, while you watch this."

The free site's home page did a refresh. She scrolled down. A few rows up from the bottom, we saw a rectangle showing the back of a green-haired woman holding out the sides of a blue shirt with white pin-stripes. A feathered mask looked over her shoulder. The title was, Want to Send Shirley a Boyfriend Shirt?

She clicked on it. After an ad for her platform, her video debuted.

I didn't feel any differently about it than I did when I shot it. It was fun. 'Shirley' came across as energetic, happy, and ready to have a good time with some guy's shirt. Yeah, there were her tits, and ass, and pussy, all of which I had captured in close-ups. At no time, however, did 'Shirley' give any impression that what she did was shameful. Even after what amounts to her money shot, with the front tails gulped into her folds, she showed only arousal and enjoyment.

I didn't applaud. Instead I said, quite sincerely, "Whoever Shirley is, I would really like her as a person. Entirely aside from whether she'd let me do anything with her physically."

Lois said nothing. The closing screen, with the QR code and the platform's logo, ran for its allotted seconds. Then the video ended.

"What do you think?" I asked.

She drew in a breath. Then she said, "My god, that was hot!"

She faced me with an ear-to-ear grin. "I'm proud of that! Slut, shmut! You go, green-haired fattie!"

"You took exactly the right approach," I said, finding the words for the first time. "No attempt to seduce the viewer, or stage a dom/sub fantasy. For a man to interact to the point of sending a shirt, he might have to cross a tall barrier of shame. But you've made this about two people having sexy fun. Down goes the barrier."

She clicked back to the main page, and we looked at the metadata.

Just over three thousand views, a rating of 74 percent.

Then it refreshed. Almost five thousand views, rating 79 percent.

"It's a free site," she said dismissively. But still with most of her grin.

My phone chimed.

I got it out, looked, and showed it to her. "You're going to have to do this at least once more." Then I blinked. "Um. Twice."

Now we both looked only at my phone, and the signups to send shirts.

It wasn't long before she said, "I guess I should be careful what I wish for."

***

The first shipment, of six shirts, showed up at the ShipCo store a few days later. I didn't try to disguise myself. That might have been more noticeable on the security cameras. I decided that plain ordinary me, unlikely to be picked out of a lineup, could arrive and depart unremarked, as long as I didn't act oddly.

Also awaiting pickup was an order I had placed, for two dozen sealable plastic bags, each big enough to contain a man's shirt. Once 'Shirley' was done with a shirt, it was basically medical waste. I hoped an airtight inner wrap would keep return shipments from getting undue attention. I didn't want to apply for the appropriate licensing, and might not qualify even if I did. As it was, what the clients sent to Shirley might already be medical waste. Fortunately, nobody at ShipCo said anything about what was brought to me.

It was a Thursday. I had picked up during my lunch break. Lois was at her place when I arrived after work. She had brought home carry-out Pan-Asian for us both.

She also had her own position on incoming medical waste. "I'm okay with your funk," she had told me the night before. "From total strangers? No."

We had therefore set up an unwrapping process. The six packages were laid out on her living room floor, and the QR codes were confirmed with the data we had. Lois opened them one at a time, and sniff-tested them. Four, at the very least, had been in body contact before shipment. Lois made notes that these four would get commentary from her on their manly scents. She then dispatched me to the building's basement, where I put all six in the clothes washer.

Back in her apartment, I found the food laid out for us on her kitchen island. "I'm pretty sure I can get through at least three tonight," she said, all businesslike. "Are you okay with me catching up over the weekend, if necessary?"

"Spend more time with my naked girlfriend?" I said in mock-deliberation, rubbing my chin. "And help satisfy her physically? I don't think I have anything preferable on my to-do list."

"This'll be different," she said, as much to herself as to me. "I don't think it's reasonable to have you finish me off after each shoot. We'll see if I can stay under control through several."

After we ate, I went and moved the shirts to the dryer. Back upstairs, she opened her laptop and ran her promo on the free site, and we started to make out, lightly.

"This one went nine minutes," she said, analytical despite starting to huff. "Ten to twelve should be enough." This led to me making prompter cards to hold up, to alert her to reaching two, four, six, eight, and ten minutes. "Definitely more than eight," she told herself, while reaching into my shorts and tickling. (Sadly, the 'eight' didn't refer to what she touched.)

"I still have to make another trip downstairs!" I moaned.

"Let my neighbors envy the hunk I own, in all his pants-tenting glory!"

I tended to hobble as I retrieved the shirts. I set them on the bedroom floor, behind the camera, each with Lois's notes about the client.

Lois finished arranging the backdrop, then stepped up to me. "Just a few more gropes," she said, donning the wig. "Keep me dressed."

So I worked around and within her starting outfit, fondling her breasts, single-fingering between her labia, kissing the face about to vanish beneath a mask.

With the mask in place, the room became what's known in film and video as a 'hot set,' about to get much hotter. She got comfortable, sat on the end of the bed, and nodded. I finger-counted down from five, and began recording.

"Hi Carl," she said, waving and smiling. "Are you ready to have some fun? I sure am! Thank you so much for sending me your shirt!"

She may have faked the enthusiasm at the start, but very soon Lois was totally Shirley, and giving Carl a strip show and a shirt routine, plus pleasant company (if that mattered to him while he yanked his crank). Lois paced it well without adhering to a schedule, and smoothly said "Bye bye!" at eleven minutes, nine seconds.

I turned off the ring light along with the cam, cueing her that she was done. She took a cleansing breath, but looked quite perky as she stood up. "T-shirt next," she said, lifting the mask. This kept her interested, knowing that she'd have to do different things with different shirts. She sipped from a water bottle as she carried Carl's buttondown to the array behind the camera.

I bagged and sealed Carl's shirt, which now carried the load of Shirley sweat and juice that was part of what he'd paid for. Lois walked around as she hydrated, flexing her legs. She picked up the gray sports-logoed t-shirt and her notes on its owner.

In less than two minutes, she was dressed and back in starting position. With a smile I said, "Mask." More amused than chagrined, she pulled it into place, to hide Lois.

Her nod, my finger-count, "Hi DeMorris!" Ten minutes, forty-one seconds, tails-in-pussy replaced by a careful removal that left the mask and wig in place, and a stripper's slide of the stretched fabric between her legs.

"Did it look okay?" she asked me as she hydrated, because this one was different.

"Yeah. You did plenty while wearing it. Pulling the neck down to get your breast through is a keeper."

"Thought so," she said with a smile, dropping DeMorris and taking up Mario.

The third video had an issue that she turned into a feature. Toodles, on the other side of the closed bedroom door, starting meowing in indignation over being excluded from whatever his human was doing. Shirley rolled with it, saying the cat thought he was the man in her life, but now she wanted to spend time with a real man's shirt. This became a theme on which she improvised variations, whenever it happened again.

Lois looked a little worn out after the third shoot, but said, "One more for sure." She didn't make that any easier on me, pulling up the mask and giving me a deep tongue kiss.

The fourth one was okay, with her maybe flagging a little, but I was probably more aware of that than any viewer would be. When I turned off the light and cam, she flopped on her back in bed and asked, "How many more on the way?"

I got out my phone to check tracking numbers. "Five tomorrow. Two Saturday. With some transfer points closed on Sunday, eleven between Monday and Wednesday."

"So nine to go, through Sunday night. Let's try for four tomorrow, then we can be less frantic."

Her energy seemed to droop with every syllable. As I unplugged stuff, I asked, "You gonna be okay?"

Her body shook with silent laughter. "Afraid I'm not a sex maniac right now. I'd like a very slow, sweet ravishing from you."

I did what I could to accommodate her. Then she input titles on the four videos, and I sent them off to the platform for the other prep work to be done there. Then I went home, with both of us needing enough sleep to get through in-person work on Friday.

The Friday shoot was similar. I think Lois paced herself more, knowing what she'd need to get through the whole session. She was still quite bubbly, but clearly more aware of how much time to spend on each aspect. All four vids came in between nine-and-a-half and ten minutes.

Our sex was bouncier, since I stayed the night and we could sleep in.

Saturday morning, Lois spent much of breakfast time checking messages from the platform. Five of the eight vids we'd sent were scheduled, two later that day. She was also told that one of them would be teased to the free site, to keep up interest.

The platform also told her that her first EFT direct deposit would arrive on Monday, specifically for the base fee on the approved five, and the latest receipts on the promo (also being viewed by paying customers on the platform), and the 'VIP memberships' of shirt-senders. The platform's sending to an account in Lois's real name had me more worried than any other risk, but she said her research had shown that the platform had ironclad security for providers. So far.

I saw her eyes widen. She quietly said, "Daaaammmnn."

I swallowed coffee and set down the cup, to avert having to clean up after a spit-take.

"How much?" I asked.

"Nine hundred and seventy-eight dollars and twenty-nine cents."

"That puts this whole project, after all its costs, well into the black."

She looked at me, with an expression that wasn't blank, but I couldn't clearly read it. "Slut or not," she said, "Now I'm a sex worker. And, so far, a successful one."

***

Lois didn't go into more detail than that. I wanted to know what she was thinking, but didn't want to invade her privacy. It seemed best to let her sort everything out, but I worried. About myself, as well as her. Was this new aspect of her life going to take her away from me?

Just as time might change how women felt about me, internet access could rouse men who wanted to do more than jerk off to her. I valued her fun-loving self. Clearly, other men, maybe thousands, would also. And they'd be fine with her body as it was, revealed to them fully. Heck, I thought any woman enjoying her self-pleasuring so eagerly would arouse any straight man.