It was too good to be true.

My daughter, who lived about three hours away, needed someone to house-sit for her for a couple of weeks. I was quasi-retired and able to do what work I did from “home” (read: anywhere I could get an internet connection). My wife had to pull the old nine-to-five grind at a brick-and-mortar business, so that left me to my own devices. It would be a perfect opportunity to indulge in my true passion — cross-dressing.

I packed two bags — a bag of mundane clothes and “my” bag. I was like a kid in a candy store picking through my stash of lingerie and toys. I couldn’t decide among so many sexy things, so I settled for horribly over-packing. Bras, panties, garter belts, stockings, baby dolls, teddies, heels, dildos, butt plugs, and breast forms — the works — bulged out the sides of my alter-ego’s luggage. I was struck by a sudden burst of inspiration and grabbed two final items.

I arrived mid-morning and after being warmly greeted by my daughter; she showed me the list of things to be looked after and then hopped in her car headed for the airport. I unloaded my bags into the guest room — an en-suite room with a queen-sized bed and generous bathroom. I texted my wife to let her know I had arrived and proceeded to unpack.

My mundane clothes were immediately tossed into the bottom drawer of the chest of drawers. I spent the better part of the next thirty minutes carefully folding and pairing my other “unmentionables” into the other drawers. The last few items I had packed were last and went on the top. After a light lunch, I settled in at the kitchen bar and took care of a little work.

It was early Fall, but the weather was unseasonably warm — as I knew it would be. It was time to put the plan hatched by my burst of inspiration into action. Taking the two items from the dresser I set my plan into action.

I had always fantasized about putting on a bikini, daring to go outside, and generating some sexy tan lines. As autumn was coming soon, staying covered up wouldn’t look out of place and would give any tan time to fade. My wife always showered and left the house before me most mornings and we hadn’t had sex in over a year so there was little chance of her ever seeing them.

My daughter had neighbors on either side — one single-story house and a two-story. She looked down into the backyards of the houses behind her, so I knew I would be pretty safe if I made sure to set up the chaise lounge right next to the fence of the two-story house.

I checked my daughter’s house camera coverage angles and came up with an approach that would provide me with all the anonymity I desired. I made all of the necessary preparations — setting up the chaise, laying out a few towels, and rummaging through my daughter’s bathroom for some tanning oil. Everything was set.

The bikini top was made with wide-ribbed pink fabric with underwire support. The stripes were vertical. It had straps that narrowed to adjustable spaghetti straps. I slipped my arms into it and clipped it closed in the back. I usually wore it inside and with breast forms, so I had to adjust the straps a little. I wanted the cleavage tan lines to be from the bikini, not my fake tits.

Next came the bottoms, made from the same ribbed pink fabric. They were high-cut hipsters that snugged far enough into my ass crack that it would leave an excellent tan line on my ass. I thought briefly about tucking myself but then thought better of it. I was going outside as my true sissy-self to get some sexy tan lines!

I oiled up, rubbing myself all over. The sickly-sweet smell of coconut in the tanning oil only served to make me more horny. I borrowed one of my daughter’s cover-ups which was a little too short for my frame, slipped into a pair of two-inch block heel mules, and minced my way along my chosen path to the chaise lounge next to the fence, taking the tanning oil with me so I could re-apply. Butterflies were dancing in my stomach!

The sun was bright and warm and I could feel it on my shoulders as I stripped off the cover-up. I bent over, laying one towel out on the chaise and rolling the other to be used as a pillow. I lay on my back, soaking in the rays of the sun and feeling naughty all at the same time.

After twenty minutes I rolled over, making sure to adjust the rear of my swimsuit to make the tan line just perfect. I alternated like this for the next hour or so, giving each side a couple of chances to start the tanning process. I reapplied the tanning oil every hour and after a little better than three hours in the sun I was ready to go inside.

I stood up, stepped back into the mules, and slipped the coverup back on. I minced my way back into the house for a nice cool shower. I took the opportunity while I was in the shower to insert one of my many butt plugs. When I had toweled off I slipped into a sexy bra and panty set, inserted my breast forms, pulled on a robe from the guest bath closet, and slipped back into the same mules. I settled down at the kitchen bar to check my blogs and social sites.

After a few hours, I was extremely horny but resisted the urge to jack off. I was hoping to take the time to achieve another sissygasm later and hoped to make a spectacular mess. I swapped for a bigger butt plug, added some stockings and heels, and then prepared a sensible dinner. When it was finally bedtime I slipped into a satin nightie, pulled the plug from my horny ass-pussy, and had a restful evening.

In the morning I took several dildos into the shower with me along with my chastity cage and an assortment of butt plugs. I soaped up and locked myself in my pink resin Holy Trainer-IV cage first, and then proceeded to use the butt plugs in size order. Finally, I used the dildos from smallest to largest, giving myself a thorough ass-fucking without coming.

When I got out of the shower I kept the cage on and re-inserted my six-inch penis-shaped butt plug. I got back into my pink bikini and did a little work. At one point as I was working a video call came in from my boss. I was startled but quickly slipped into a sweatshirt. It gave me more than just a little thrill to know that from the waist down I was caged in pink bikini bottoms while I video chatted with our management team.

As the sun rose higher, I went out for another tanning session. Just as the day before, I kept my route away from my daughter’s cameras and spent about three hours rotating from front to back, feeling just a little more naughty for being outside in my chastity cage.

After lunch, I did a little more work in my bikini and then went back out for another session. After another few hours of baking, I came back in and took a nice cool shower. Since I had kept the penis-shaped butt plug in all day I went straight back to the dildos for another ass-fucking session. After this shower, I went straight to a blue satin babydoll nightie. I kept my cage on and inserted my medium-sized Square Peg Egg plug in pink. This evening I placed my breast forms in the bust of the nightie and added a pair of white lace-top stay-up stockings. Stepping into a pair of white patent four-inch pumps completed the outfit.

I spent the evening teasing and torturing myself by chatting online with a few fellow CDs and browsing my blogs. My caged clitty leaked and by bedtime, the front of my panties was completely soaked.

The next morning was a repeat of the previous day, only without the video call. As I dressed in my pink bikini for another day in the yard I could see tan lines! My clit jumped in my cage, quickly swelling to uncomfortable. I was so excited about two more sessions of tanning. Tomorrow, I told myself; tomorrow I will do a nice picture set to show off my new tan lines and film a good ass-fucking session that hopefully ends in sissygasm.

After my afternoon tanning session, I was heading into the bathroom when the doorbell rang. I ditched the coverup and threw the bathrobe on, knowing it would easily hide the lines of my bikini.

I looked through the peephole and saw my daughter’s neighbor, Terry. He lived in the two-story house next door. I had met him and his wife Mandy a few times before. They were a nice black couple with a few kids and dogs that constantly got out and into my daughter’s yard. I presumed he was here to talk about the dogs so I tightened the belt of the robe and opened the door.

“Hey, Terry,” I said. “You caught me on my way to shower. What’s up? Dogs get out again?”

“Can I come in?” he asked.

“Sure.” I opened the door wider and stepped back, letting him inside. He was in a gray sleeveless tank with his NFL team on it and a pair of baggy athletic shorts. His arms were covered in a light sheen of perspiration. “What can I do for you?”

“Have we ever talked about what I do for a living?” he asked. “I mean, my side hustle, not my job-job?”

“I don’t think so, no. I have noticed that you have a reference to being a licensed drone operator on the back of your truck. Does it have something to do with that?”

“It does, and that’s what brings me over here today. See, when I’m getting ready for a big drone job I have to calibrate everything. Mostly I measure real estate tracts for developments and stuff like that, but my measurements have to be almost exact. So I have to fly a test run and measure something I know at the same height from which I’ll be operating.”

“I see; well, yeah I can see how that would be important.” I tried to sound casual in my interest but the butterflies I had had that first day I stepped outside had returned.

“So I always just measure my own backyard, see? I know where everything is. I know how tall the kid’s playset is, how wide my fence is — all of it.”

“Makes sense,” I said. My mind whirled and the next words he spoke, while unexpected, were not completely out of left field.

“Well, I did my calibrations over the last few days for a new job. I came home early today to double-check everything and saw something unexpected.” I watched him closely while trying not to appear to be watching him closely. I could swear his cock was starting to tent out the front of his shorts. I suspected he wasn’t wearing any underwear. “I saw you sunbathing in your pink bikini.”

I felt my cock surge in my cage and I just knew the pre-cum was already flowing into my bikini bottoms.

“Terry…I, uh,” was all I managed. Every sissy dreams about the time they finally get caught, right?

“Are you still wearing it under that robe?” He unconsciously grabbed the growing bulge in his shorts. “Will you show me? I thought I saw the outline of a chastity cage. Am I right?”

I had been with a few other crossdressers before — years and years ago, but despite the robust fantasy life in my mind I had never actually considered being with a man.

I felt my hands move woodenly to tug at the belt of my robe, letting it fall open. The flash of pink under the white robe was undeniable. If I had not been caged my bulge would have been undeniable too.

He stepped toward me, tugging at the shoulders of the robe until it slipped to the floor, leaving me standing there in just my pink bikini. He looked me up and down, rubbing the tent in his shorts.

“You look amazing,” he said. I felt the blood rushing to my face. His hands were on my shoulders again, this time applying gentle pressure. There was no mistaking his intentions. Something long-suppressed in my subconscious mind bubbled quickly to the top.

I knelt in front of him and he stepped even closer. His cock was getting hard and straining against the fabric of his athletic shorts. I reached for the waistband and he pulled back.

“Are we going to do this?” he asked. “If you pull down my shorts you’re going to have to suck my dick.”

I sat back on my heels with my legs spread. I rubbed between my legs, stroking my caged clitty before moving my hands to my chest and squeezing my titties, and pinching my nipples.

“What would your wife say?” I asked him, addressing the 800-pound gorilla in the room. “For that matter, what would my wife say?” I thrust my chest out and cupped my cage, jiggling my package up and down in my bikini bottoms. I had made my decision.

He stepped closer and this time allowed me to tug at the waistband. As I pulled them down his cock sprang free, hitting my chin. It was easily ten inches long and covered with a wet sheen. I opened my mouth and took the first four or five inches inside. I swirled my tongue around the head as I closed my lips and slurped on his member.

Terry moaned.

With my mouth on his cock his crotch was close to my face. As I breathed through my nose I smelled pussy. I realized I was tasting that pussy — and cum too — on his cock. I pulled back.

“Did you just fuck your wife?” Terry moved his hands to my head and guided my mouth back on his cock. I opened wide, sucking even more of his cock in my mouth and partially down my throat.

“Oh, God yes,” Terry said. “Suck that dick. Suck that dick that just fucked Mandy’s pussy and filled her with cum!”

I moved my head with Terry’s guidance, using my lips, mouth, and throat to please his cock.

“As soon as I realized what I was looking at my dick started to swell,” he said. “Then when I realized it was a caged sissy clit in those bikini bottoms my cock was instantly rock-hard. Mandy came in and thought I was just looking at a porn site and seeing my hard dick made her horny. What else was I supposed to do?”

“It’s kind of hot sucking your wife’s pussy juice off of your cock,” I said. “I hope you saved some cum for me.” I moved my mouth from his cock down to his balls. I gave his ball sac a good tongue bath, gently sucking first one, then the other; finally holding both balls in my mouth at the same time.

“Oh, fuck yes,” Terry said. He pulled my mouth away from his balls, clearly so I could resume sucking his cock. “I still have plenty of cum for you.” I filled my mouth with his cock and forced it all down my throat.

Blood was pulsing in my ears as he fucked my face. I gasped for air when I could, but I wanted to feel his cum filling my mouth. His balls collided with my chin with each thrust as I worked his cock.

“As soon as my wife came she passed out, dead asleep. I threw this on and came straight over. I hoped it would go this way.”

“Mmm-hmm.” I was barely able to gurgle a response around his cock. I stopped deep-throating his cock and switched to sucking just the top four or five inches, swirling my tongue around his glans each time. I stroked the bottom of his shaft with one hand and massaged his balls with the other.

“Give me that cum,” I said. I looked up at him with his cock in my mouth, sucking hard. “Fill my mouth with your hot seed!” I plunged his cock back down my throat.

“Shit, you’re going to make me blow my load!” he said. “Ohhh fuck! Here it comes! Here it… Unnghh.”

I felt his cock swell in my throat and I pulled away until just the head was in my mouth. I cupped his balls, feeling them pulse. I felt the first spurts of his cum hit the roof of my mouth, his cock head expanding and contracting as his balls emptied themselves into my mouth.

He moaned amid a torrent of unintelligible sounds.

I kept my lips locked around his cock until he was spent, savoring the taste of his cum. When I finally released his cock, I opened my mouth, showing him his load. I swallowed, licking my lips, and then swallowed again.

“I would have loved to swallow your first load,” I said. I suckled at his softening cock, making sure I got every drop. “Next time I hope you’ll come and see me first.”

“Next time?” he asked.

“Well, I sure hope so,” I said with a mischievous grin. “I have eleven more days until my daughter gets home.” I turned around on all fours and wiggled my bottom at him. I looked over my shoulder as I tugged my bikini bottoms to one side, releasing my caged clitty and displaying my puckered brown hole.

“Shit!” was all he managed.

“I was hoping you might want to sample this sissy’s pussy,” I said.

“Oh fuck, yes!”

I turned back around, my clitty leaking pre-cum from my cage as I knelt in front of him again. I pulled his shorts up, pausing to give his cock a goodbye kiss.

“You can call me Stacey, by the way.”

“Stacey. Right.” He crossed the short space to the door.

“Stacey, your sissy cocksucker,” I said, registering the priceless look on his face as the door closed between us.