A gay story: Weekend Work Trip Pt. 02 Part 2 of 3.
SATURDAY AFTERNOON.
Mr Anderson placed his hands on my hips and turned me to face the large floor length mirror. He stood behind me, his strong hands caressing my flat stomach and thighs as we stared at each other’s reflection. My body was so smooth and feminine compared to his tanned muscular physique, my head was still spinning from the joint we’d shared and I leaned back into him feeling his cock hardening in his speedo against my tight ass. It was all so new and unexpected, I still couldn’t believe I was here sharing a hotel room with my hot sexy boss and more that I had just sucked his big cock to completion with very little convincing.
His hands caressed the thick bulge in my tight bikini briefs and I heard myself whimper as my hands reached back and gripped his thighs. Mr Anderson hooked his thumbs into the waistband of my underwear and slid them down my thighs, my hard hairless cock standing fully erect.
“You’re so smooth and sexy…” he whispered in my ear as his hands wrapped around my erection and he began to gently stroke it. “Are you ready to get dressed?”
“…..yes…” I whimpered.
“Yes what?” He asked sternly.
“…yes Daddy…”
“Mmmm…good boy…” he said as he reached into the bag with his free hand, pulling out a small chrome butt plug with a pink jewel in the base. He held the plug up to my lips and I kissed it before sliding my tongue out of my mouth and licking the hard little toy. “That’s it baby… get it nice and wet…”
He slid the plug into my mouth and I started to suck it, treating it like the tip of his cock, working it with my lips and tongue as he massaged my trembling erection. Without a word he turned me to face the bed and bent me over, I leaned down on my elbows and spread my legs, completely under his control. He ran one hand down my spine causing me to shudder and then pressed the slippery plug against my smooth pink hole. Mr Anderson gently pulsed the toy against me and I moaned involuntarily, my cock throbbing hard as the pressure from the plug sent waves of pleasure through my whole body. Suddenly he pushed it all the way in and I gasped, gripping the comforter as the plug slipped into place. He pulled me up to face him and kissed me deeply before asking, “Does that feel good baby?”
It did. SO good. I’d never felt anything like it before, heightening how stoned I already was and driving me wild with pure lust. The plug was pressing against all the right spots, causing my eyes to roll back in my head as he pulsed his ring and middle finger against the base. Was this what anal sex felt like? If so I suddenly understood what all the fuss was about. My cock was rock hard, pressed against his speedo bulge and I moaned, “Yes Daddy… it feels sooooo good…”
Mr Anderson smiled. “Good…” he said “Now let’s get you ready.”
He reached into the bag and pulled out a pile of clothes, selecting a few items and laying them out on the bed.
“First things first…” he said as he held up an impossibly small white g-string. My heart pounded, wondering if he actually expected me to wear it. He dropped to his knees and had me step into the tiny thong before sliding it up my long smooth legs and pulling it into place, taking care to tuck my hard cock into the front pouch. The g-string was made from some incredibly soft stretchy material so even with my giant erection the tiny garment was able to provide adequate coverage. Barely. He pulled the thin side straps up high over my hips causing the thin back strap to pull tight between my cheeks and press against the base of the plug. He handed me a thin white mesh tank top that I pulled on over my head as he had me step into a small pair of bright pink spandex hot pants. He slid them up over my tight curvy ass and snapped the waistband against my hip, flashing a smile and causing me to giggle. Mr Anderson handed me a pair of large dark sunglasses with gold frames and a small rhinestone heart on the left lens. I slipped them on as he had me step into a pair of hot pink sandals. He stood and told me to make a kissing face, I obeyed and he proceeded to apply a thin layer of pink lips gloss to my pouting lips and tosseling my shaggy brown hair before stepping back smiling and admiring his work.
“Oh yes…. You look amazing.” He said proudly as I turned to the mirror to inspect my new look.
My pulse raced. I looked so slutty. The outfit was so revealing and feminine, so tight on my smooth skinny body. The tank top didn’t even reach my belly button and was so thin that my stiff nipples were clearly visible through the soft semi transparent material. The hot pants hugged my curves and the thin g-string straps wrapped high over my hips directed attention to my thick bulge and tight curvy ass. The only thing missing was a red lollipop for me to suck on to make me look like a totally insatiable boi slut. The tight clothes felt incredible against my smooth skin making me feel incredibly feminine and exposed as my cock throbbed hard in my tight little panties.
“Does this make me look too…. Gay?” I asked, looking up at Mr Anderson.
He smiled, “No baby. You look amazing… and you feel sexy don’t you?” I nodded and he continued, “And there’s nothing gay about dressing sexy and showing off your hot body… plus now everyone down by the pool will be able to see what a sexy femboi assistant I have.”
My heart swelled, proud that Mr Anderson found me so sexy. I was still riding the high of the joint we’d shared and combined with the sensation of wearing a plug for the first time and feel of my new slutty outfit, I was more turned on than I’d ever been in my life. It was all so exciting and confusing, embracing these new feelings of arousal and desire all under the supervision of my hard sexy boss was incredibly hot. I loved hearing him call me a femboi, was that what I was now?
Mr Anderson slid his speedo down and reached into the bag, pulling out a hot pink lycra thong that he pulled on over his confident erection. “There.” He said, flashing me a sexy smile, “Now we match.”
He pulled me in for another kiss and I whimpered softly, our thick bulges pressed together as my fingers traced the “T” shape of the back of his tight thong swimsuit. I felt so slight and girly in his muscular arms, so submissive as he gazed into my eyes.
“Ready?” He asked.
“Yes Daddy.” I purred as he grabbed two towels, took me by the hand and led me out the door.
We took the elevator to the lobby, walking past several well dressed men who sat in leather armchairs. I could feel their lusty eyes on my body as I followed Mr Anderson out to the patio, my eyes fixed on his tight ass as he strutted confidently in his tight pink thong. I must have looked like his pet as he walked me through the lobby and I wondered if the men were here for the conference too.
We walked out into the sunshine, along the large swimming pool, its crystal blue water lapping at the sides and he selected two lounge chairs across from the tiki bar with a thatched roof.