An Open Door Policy

An Open Door Policy

Ryan and I work together. We are both work as supervisors for the installation of our company's equipment. While the both of us are responsible for different aspects and installations, some projects required both of us to travel together for the same project.

Ryan was a fantastic and hard worker with whom I've never had issue with. Because of our work, we've become good friends. I had long known he enjoyed wearing women's underwear and I am totally fine with it. How I found out is another story that I may embellish later.

A few co-workers at the office also knew that he crossdressed and are also fine with his choice as long as his work was not an issue.

If Ryan wore anything to the office, it was always hidden under his regular male clothes; usually a slightly oversized but stylish suit and tie. His background was Korean (I believe). He stood at five-five, three inches shorter than me. I knew his hair was long but it was always tied back into a pony tail and hidden by his jacket. I really couldn't tell his body shape but I know it was probably on the slim side.

His cheeks were smooth and I doubted he even shaved. He had big eyes in that stereotypical shape that you see in those AI generated models. But the biggest feature was the length of his eye lashes. They were natural and exceptionally long. Many of the girls and women at the office often mentioned how jealous they were of his lashes.

We were co-assigned the project in Vancouver. The install required integration with each other's and it would be more than a couple of weeks to complete. Long story short, the hotel we were booked in had us in adjoining rooms with doors in between. The rooms were quite big and comfortable so no complains there.

"Jer." Ryan used the shortened version of my actual name, Jerrold. "If it's okay with you, we can leave the passage open but close it if we need... you know, privacy."

"Sure, Ryan. You know I've got no problems with anything." I answered. "And besides, it would make it easier when we need to communicate with each other about the install."

The first week was rough for me and took a lot of extra time to meet the schedule with Ryan's. The customer crew I worked with was great and went out of their way to make sure we could meet the timeline. By the following weekend, we were on track and the integration could start. In fact, we were a tiny bit ahead and so no OT required over the weekend.

I got back to my room by mid-afternoon. Ryan was still out and I was feeling grubby so decided to have a nice, hot shower before dinner. When I was done, I wrapped a big, fluffy towel around my waist as I dried my short hair. I looked over and found that Ryan had left a note asking me to review and sign-off on the papers he left on my table. I looked them over and signed them.

The door between our rooms was open so I reciprocated and when to drop the off back in his room. Then something caught my eye on his bed. White panties.

I was taken aback at first and was really uncertain but my curiosity overpowered my sense of privacy. I picked them up and held them. They were white lace in the front with I was guessing a satin bum. I did recognize they were thongs that would ride high on the hips. Marking the back was a big, white satin bow with five or six inch tails. I carefully took a sniff. Then another and another. They seemed to be clean and unworn.

I was about to replace them as I found them but my hard on had forced its way through the slit of the towel around my waist. I stood there again unsure what to do but the urge was too strong. And so I wrapped the panties around my boner. The feeling was soft and sensuous as my hand involuntarily started stroking my shaft.

I didn't know how much time I had as I ran back to my room and let my towel fall to the floor before I jumped onto my bed. I covered my knob with the thong and continued stroking. The soft satin and lace made me harder than ever before as I felt the cum in my balls start to boil.

My breathing was hard and raspy then suddenly I exploded. Wads and wads of hot cream filled Ryan's panties until I had no more to give and I collapsed into a panting heap. It took a few moments until I realized what I had done.

The panties were stained and saturated with my cum. There was no hiding the huge, dark, wet spot on the satin part. If I washed them out, I doubted there was enough time for them to dry. So still naked, I cleaned them tissues as best I could, dashed back into Ryan's room and place them back on his bed.

I quickly dressed and was about to leave when I heard Ryan return. "Hey, Jer. Thanks for signing the papers!"

There was a big, uncomfortable silence with Ryan appeared in the open doorway. Dangling from his index finger was the cum-soaked panties. "Jer, was this you?"

Embarrassed and ashamed I hung my head down and nodded yes. "I'm so sorry for invading your privacy. I returned the papers and saw them there and I... I'm sorry."

"Well..." Ryan started and gave me a stern look. "What should we do about it?"

"I... I don't know." I mumbled. I was scared shitless. A report to HR could terminate me. "I know it won't make it up to you. Let me buy you new ones for ruining those and dinner. Anywhere you want to go. On me."

I could see Ryan considering the offer. He narrowed his gaze towards me and measured my predicament. He tossed the cummy thong at me. "You keep these. Yes, you can take me to dinner but you'll need to dress up. Give me some time and I'll meet you in the bar downstairs in about an hour."

With that, Ryan closed the door between us. I sat on the edge of my bed shaking my head in disbelief. His words "you'll need to dress up." echoed in my brain. I removed the polo shirt and slacks that I had on and buttoned up a white dress shirt. Formal wear really wasn't a requirement for the job but I had brought a couple of suit just in case I needed them. The candy apple tie I had went well with the black suit.

I checked my watch and still had forty minutes to wait. I thought about knocking on the door to let Ryan know I was ready but again his word of "meet you in the bar" played in my mind. So down to the bar I went.

I sat and ordered a nice single malt; neat with ice water on the side. Nervously, the first one went down easily without much thought and still time to wait. About an hour and a half later, I was about to order my third when I spot this incredible looking woman enter the bar. She stood at the doorway and looked around before approaching. She was elegantly attired in a slim, knee length, sleeveless, shoulderless, black dress that showed off her tight but shapely body. Her shiny legs told me she wore stockings and I could make out the reinforced heels and toes with the black, steel shanked stiletto, sling backs she had on. The heels had to be at least four or more inches high.

She had long black hair that draped over her nice sized breasts. Not too big; maybe a B? A long string of perfect pearls was around her neck. Perfectly painted red lips. Her make-up was perfect and barely noticeable. Dangling from her ears were matching pearl earrings. Then I was pleasantly shocked when she smiled at me and asked if she could join me. I automatically asked. "Of course. May I buy you a drink?"

She nodded and smiled.

"You don't recognized me at all, do you?" I shook my head no to her question. Now maybe I was stupid but maybe I was stunned by this beauty who giggled and placed her slender hand on my arm. "It's me, Ryan! But please call me Rylan."

My jaw literally dropped as I carefully took a second and third look at him... her... Yes the features of Ryan were there but were expertly softened by her make-up. Even then, it took a few moments to accept.

"So Jer. If you don't want to, we don't have to go to dinner or anything." Rylan told me. "I can go out on my own and you don't owe me anything. And the panty thing? Well that will be our secret."

"No! No! Please, Ryan... I mean Rylan. Please stay." I stammered. "I'm just amazed and pleased. And would love to take you to dinner. And I love your name too. So cleaver just to add the el in between."

"Good. I was afraid that even though you knew, with me changed then going out might put you off." Rylan smiled. "I am grateful for your company and invitation. Honestly, I do go out dressed but I don't go out on dates like this."

We had a couple of more drinks at the bar. Talked a bit more. Laughed a lot. And enjoyed each other's company, but no business talk other than office rumours.

Rylan selected a restaurant not too far away but far enough to take a cab. In the back, I took her hand in mine and kissed it. After which, she placed her hand on my thigh. The tips of her painted finger nails touched my hardening cock. I leaned to her and kissed her on the cheek.

We were soon at the place she choose. I paid the driver and in we went. There were tables surrounding a dance floor and booths along the walls. Ryan turned to me and said. "This isn't just a regular restaurant. It's an old style dinner and dance place with live music. I just love this kind of place."

"Wow! This is amazing." I looked around like an idiot. "Big band? I hope so. One of my favourite types of music."

Rylan nodded. "Actually there are two bands tonight for almost uninterrupted music. A special singer tonight too!"

Dinner was great. Shrimp cocktail for me and smoked salmon for Rylan as apps. For mains, I had the Dover sole and she had scampi. She offered me a bite of hers and I reciprocated with mine. We talked more and laughed a lot. I only hoped she was enjoying herself as much as I was. Dessert was crème brule, my favourite and apparently hers too. The burn sugar on top was just right and the custard beneath was smoother than a baby's bum.

As coffees and cognac was being served, the band started. They were great playing all the standard big band sounds: Dorsey, Shaw, OP and the Duke. Their incredible clarinet player mimicked Glenn Millar flawlessly. Millar was my most favourite leader. Moonlight Serenade started to play and it brought a happy tear to my eye. Rylan noticed and wiped it away. She took me by the hand and lead me to the dance floor. I held her in my arms; she felt so perfect as she laid her head on my shoulder. There may had been a dozen others dancing but I felt it was just the two of us.

Another slow song, this time by Oscar Peterson started. She snuggled into my neck. I pulled away a bit and I think she was taken aback thinking she had gone too far. But I alleviated her fears by placing my lips against hers. I felt her relax in my hold as her tongue slipped into my open mouth to play. "Rylan. You are so beautiful. I could dance with you forever."

Rylan pulled away. It was my turn. Was I too early to make such a comment? But there was now was tears in her eyes and a quiver on her lips. "Jer. I need to tell you something first and I really hope this doesn't change anything."

Now I was really concerned but still none the wiser. I still held her although we were barely moving on the floor. I looked at her with puzzlement.

"When I left the papers for you to sign, I left the door open and knew you would return them to my room." Rylan started. "I left those panties out for you to see on purpose. You see, since you found out about my... you know, dressing up, your attitude and friendship never wavered. I found that very attractive. The more and more we worked together, the more I fell for you. I'm so sorry."

"Oh Rylan! No, don't apologize." Tear welled up in my eyes too. "I wished you would have told me before. Yes, I like you as Ryan but as Rylan, I have fallen head over heels. And I'm super happy about that."

We gave each other a big, warm hug and a passionate kiss. It was then we both realized the music had stopped and we were alone on the dance floor. Embarrassed, we giggle and returned to our table. A few others laughed as others clapped.

We danced the rest of the night until the last song played. We grabbed a cab back to the hotel, making out in the back. I made sure to give the drive an extra big tip.

Back in my room, we continued to mash our lips together as our tongues intertwined. I found the zip on the back of her dress and pulled it down. I helped her step out of her dress. My jaw dropped once more at this beautiful woman stand before me. Beneath, Rylan wore red lingerie. A three quarter cup lace bra and matching thong panties. Her stockings were held up by her six strap garter belt.

What was more of a surprise to me was that Rylan wasn't using breast forms but had real breasts. Her nipples weren't big, maybe a little larger than pencil erasers but they wore diamond hard and perfect. When I looked at her, she could read my mind. "I've been on hormones for a number of years now."

I knelt before her and started to pull down her thong to her knees. Her little, hard, uncut dicklet couldn't have been more than a couple of inches long; three at the most. I couldn't help but take it into my mouth. With her testicles about the size of small marbles, her balls too.

The first cock I've ever sucked. I wasn't sure I was doing anything right; just what I thought I'd like. Rylan held my head and fucked my face. So maybe I wasn't that off.

As I gently mouthed her, I took hold of the backs of her thighs and slipped my fingers under her garter straps. Slowly I let them rise upward and grab her firm, round butt cheeks with my hands. I pulled her in wanting to take more of her in. Then suddenly there were tiny but strong squirts of her warm cum spurting into my mouth. I was taken aback by not only her climax but the amount of cum filling my cheeks considering the size of her balls. Enough cum to leak from my sealed lips.

She stopped moving as I swallowed her gift without releasing my hold. Rylan spasmed and pulled away from me. I looked up at her and she was smiling down at me. She was having trouble standing. "Oh fuck, Jer! I'm sorry I didn't warn you, but that was incredible and it caught me by surprise. You must have done that before."

"No, this was my first time." I confessed as I stood to supported her. "And I enjoyed every bit of it. And only because it was you. But I was surprised by how much cum there was."

"One of the benefits from being Ryan." Rylan planted a hard kiss on my lips. She forced her tongue through and tried to clean out her jizz from my mouth. "Mmmm...."

My cock was so hard, it was amazing it didn't rips through my pants. As I slipped off my jacket and undid my tie, Rylan knelt before me to undo my trousers. My anxious, fumbling fingers had trouble undoing my shirt buttons. I ended up just tearing it open.

Rylan pulled down my pants with my underwear and allowed my hard dick to pop out. It's only about six and a half inches long but it felt like it was twelve. She held it with her hand and gentle stroked it. "I love uncut cocks! It so sexier that way."

Holding it still, Rylan brought her lips to my tip and tenderly kissed my pee hole which had a bead of pre-cum leaking out. She lusciously licked her parted, red painted lips and enclosed them around the top part of my knob. Slowly she let me enter inside her until I was down her throat and her lips were around my base. Rylan slowly and seductively sucked my cock, edging me to the brink then pulling me back.

I held the back of her head and wanted to shoot my load but instead, she guided me to the bed and moved between my legs. She returned to her sucking as she spread my legs. Her palm replaced mouth as she looked up into my eyes and asked. "Are you ready for more?"

Unsure, I nodded yes.

With that, Rylan pushed my knees up as she lowered her head. Rather than taking my cock back into her mouth, she started to lap my balls with her hot, wet tongue. She sucked my entire sack into her mouth and played with them as she stroked my shaft. Each time I begged her to let me cum, she'd bite my sack telling me no.

Rylan pushed my legs up higher and almost to my chest. She ran her tongue along the entire length of my crack. She paused and then she pierced my asshole with her tongue.

Now I've had toys up my butt but rimming was the first time. Her tongue was strong and long. I felt it wriggle about trying desperately to reach my prostate.

I was so hard it hurt. I needed to cum so badly I was begging Rylan for release. She released my legs and mounted me. She reached behind and pulled the slat of her thong aside before she placed my dick against her bud hole and let me slide inside.

This too was another first. All the women I dated (or bought) were reluctant to do anal.

Slowly at first, Rylan moved up and down. I was so close to the edge, I raised and lowered my hips to match her rhythm. Gentle at first, then she begged for it harder and harder. The slapping of my hips onto her ass was loud as her breathing became hard and rasping. I too was panting harder and harder.

"Fuck! Fuck! Fuck!" I screamed. "I'm going to.... C... c... c... u... u... u... m...! Uuuhhh...! Uuuhhh...! Uuuuuuuhhhh.....!"

Anything I had in my balls shot into Rylan's receptive ass. With my final thrust, she screamed out. "Yes! Fuck me! Yes! Oh fuck that feel so good! Fu... u... u... ck...!"

Exhausted, we cuddled with Rylan spooning me from behind. As small as she was, I could feel her tiny dicklet poking my bum until we both fell asleep.

We continued to enjoy each other as Rylan and Jerrold for the rest of the time there. On the project or back in the office and she dressed as Ryan, it was easy to hide our relationship (her idea). But on dates or at each other's place, we were Rylan and Jerr.