Autumn by Marina

1. The Setup

Marina and I had developed a friendly banter for over a year at work. She was a fit 26 year old, 5'8" tall, with curly brown hair dyed red to her shoulders. Early on I had asked her out and she turned me down. A few days later she confided that she was a lesbian. After that it was a rare week that I didn't teasingly ask her out again, knowing what her answer would be. She always would say no, unless a group of us were going somewhere, but she would tease me back so I knew she enjoyed the attention.

So when I asked her out for about the 50th time and she said yes I was shocked. "Yes?" I asked for confirmation.

"Yes," she replied.

"Wait a minute, now I'll have to think of something to actually do..." I paused. "How about mini-golf then drinks?"

"Tame, but OK for a first date. OK, on one condition..."

"Well, I've only been asking you out every week for a year."

"My thoughts exactly. So you've got to buy purple panties and wear them."

"What?"

She reassured me, "No one will know what you're wearing under your pants, except me, and that's my condition."

I gave her a look.

"Come on, you've been asking me out every week for a year, and I finally say yes... if you'll just do one little thing. Why not?"

"OK," I agreed submissively.

Our date was the next night, so I couldn't take the easy way out and order them from Amazon-they wouldn't arrive in time. I didn't go straight home from work. I went to a Target 20 miles out of my way so I wouldn't be seen by anyone who knew me in the women's underwear section. Although I was 180 pounds and 6' tall, I only vaguely knew anything about women's sizes so I went with a large pair of high-cut bikini panties. When thinking about them earlier I wanted some material to keep everything in place, so anything like a thong didn't seem right. On the other hand, I figured Marina wanted something a little interesting so at least this style had a lace waistband trim.

I slipped on the purple high-cut bikini panties. They felt soft and I somehow felt relaxed but energized when I put them on. My cock was a little excited, but it must have been the idea of going out with Marina. Over the panties I wore my usual tan pants, a blue polo, brown socks and brown shoes. I drove over to Marina's apartment building and knocked on her door promptly at 7pm. She came to the door wearing a white polo, purple skater skirt and white sneakers. Her makeup was minimal, and she wore her usual gold stud earings and a matching necklace. She gave me a kiss on the cheek and we walked to my car.

As I turned on the engine she said, "Oh, I need to check one thing." She proceeded to pull the one side of my shirt out a little and pulled down the side of my pants an inch or two revealing my panties. "Oh, looks good! Otherwise I'd have to get out. Let's go."

We had fun teasing eachother over our mini-golf game, then went to the bar next to her apartment complex.

Over drinks I asked, "So why are you giving me a chance now?"

"Well, my girlfriend and I broke up, so I thought I might as well go out and have a good time... I don't know if this will lead to anything, but we'll see."

"What can help this lead to something?"

"Easy big guy. Just let whatever happens, happen. I'll definitely give you hints to keep me interested. Making you wear panties," she giggled, "was a first step... now I know you'll go the extra mile for me."

By then we had finished our drinks, so she invited me back to her place.

We sat on her couch. "Since you did what I asked and I did have a good time..." and she started kissing my ear. It felt so amazing! Better than kisses just about anywhere else to be honest. She then alternated kissing my ear with my lips. As we kissed I tried to move her hand toward my pants.

"Nope," she said but in a teasing way.

"Awww. You're going to send me home completely frustrated?" I asked.

"Well, this is kinda hard for me. I like you, but you know I prefer girls..." She paused as if an idea occurred to her. "OK, if I get you a bra too, and you wear that, then I'll stroke you."

It was my turn to pause. The alternative was nothing, so I said, "Deal."

It turned out to be a better deal than I expected because the next thing I knew she was taking off her top and unfastening her bra. I took in her beautiful breasts just before and after she lifted off my shirt. She handed me her white bra. A quick glance at the tag showed she was a healthy 34D. "Just put your arms through the straps... I don't want you to stretch it out and ruin it."

Once I had done so and laid back she pulled down my pants revealing my panties. She was seated on the couch and I was laying down on it, my legs on top of her legs. She started to caress my penis over my panties as we kissed. She then rolled my panties down a bit and started stroking as we continued to kiss. It didn't take long before I came.

"Wow, 60 second man there," she teased. I started to mumble and apologize. "It's OK, kinda cute... don't worry, I can probably help with that if you want to continue doing this."

"Oh yes, definitely... Can I help you?"

She got up, still topless and comfortable with her body, and handed me some paper towels as she said, "Well, maybe... but as you know I like girls so this is a bit of a struggle for me to consider dating you. Perhaps... if you want to try eating pussy, you could, if I do your makeup...?"

"Umm... I'd love to help you cum too, but I'm not sure if I'm comfortable with that." Maybe because I had just had an orgasm I wasn't too eager to do whatever she wanted.

"It's OK, I understand. I guess I was wrong about how interested you were in me..."

"Yeah. I'm not ready for this." We said our goodbyes and I went home.

--

The next week at work was awkward, but we tried to play it off. I looked through my contacts that week to see if there was anyone I could ask out. I was turned down twice. I ended up going out to a bar with friends that weekend, but didn't meet any potential dates.

The following Monday at work Marina and I were leaving the office at the same time. "How are things going?" She asked.

"Good," I politely replied.

"Got any potential dates lined up?" My expression gave her the answer. "Well, my offer is still good."

"What offer is that?"

We were walking to our cars and no one was in earshot. She answered, "Let me make you up and then we can hang out at my place for a while."

I don't know if it was my lack of success getting a date otherwise, having nothing better to do, or something else, but I said, "OK, but we have to take it off before I leave your place."

"Great! be there at 8. Get a close shave, and don't forget your panties." She then gave me a quick kiss on the cheek.

After dinner I took a shower, shaved, dressed, and drove to her apartment. She greeted me at the door with a kiss of my ear and slid one hand down my pants to ensure I wore panties. She smiled and escorted me to her bedroom vanity. She had two chairs next to it.

"Let's match!" she suggested. "Just bras and panties." We disrobed and she gave me an old bra that roughly matched the panties I was wearing.

Half an hour later I had on foundation to match my skin, blush, lipstick, eyeliner, eyeshadow and mascara. I had no idea so much went into it. But I didn't really look like a girl. She put the makeup on me at her dressing table, so we were already in her room. When she was done, she grabbed my hand and helped me up, then she moved to the bed and sat on the edge. She then turned on some music, then pulled down her panties.

"Making you up got me so wet already," she said as she gave me a kiss and guided my face to her pussy. I started kissing around it and she said, "I appreciate the foreplay, that's very sweet, but I'm ready for your tongue." So I parted her lips with my fingers and started on her button. Her clit was so swollen I found it immediately and focused on that. She was really close already.

"Look at me, honey," she ordered as I tongued her clit vigorously. I looked up and she came. Unlike with guys where the excitement is focused on one area, her orgasm shook her whole body a few times. I continued to lick until she started to close her legs to signal she was done.

Marina motioned for me to lay down on the bed next to her as she moved back to get her head on the pillow. I was just wearing my panties and her bra. She was wearing nothing. I turned on my side to lay against her. She felt my excitement and rolled my panties down a bit and started to stroke me. We kissed. I came, my cum squirting on her stomach. She took a finger, smeared it in cum, and moved it to my mouth.

I waved a hand, "Oh no." I was suddenly having second thoughts about all this. "I don't want to do this anymore. What are you doing to me?!" She has half apologetic and half upset. I quickly put my clothes back on as she got makeup remover wipes and handed them to me. I quickly removed what I could and left.

-

I avoided Marina at work after that. I tried to use the bathroom that didn't make me walk past her desk. If there was a meeting see would be in, I'd get there a minute late so I wouldn't have chat before starting. I'd park away from where she usually parked. She didn't go out of her way to try to find me.

I also was doing my best to find someone else to date, but continually striking out. After a month and only two dates that didn't go anywhere I was feeling dejected. I decided to start working out, so I went for a run. After my run I took a shower. When I stepped out I realized my mistake: I had put all my laundry in the wash before my run and had no clean underwear left! Except for the one pair soaked with sweat from my run (Gross!), they were still finishing in the washer.

Then in the corner of my closet I saw the package of panties I had bought for my first date with Marina. Well, who'd know? And they did feel comfortable when I wore them before. So I slipped on another pair. These were simple black in the same high cut pattern with a lacy band. I put some sweats and a t-shirt on top.

As soon as the wash was done I threw them into the dryer so they would be ready soon. But somehow I was feeling turned on. I couldn't wait. So I pulled up a porn website and started looking for something to watch. My usual was lesbian porn. I started getting into it and because I had other things to do, I finished quickly.

The clothes still weren't dry, so I had to pull my panties back up and put the sweats and shirt back on. Half an hour later I has horny again. I pulled the porn site back up and this time I stumbled on a lesbian video that included a transgender girl. That was new to me and just what I needed-something familiar but a little different.

After I finished for the second time, the dryer was done so I changed back into my regular clothes.

The next day at work I saw Marina. Just in passing. She smiled politely, so this time I smiled back, seeing no harm in being polite.

That evening was a night in anyway so after doing some reading, I felt the urge to take care of myself. This time I searched for transgender lesbian porn and soon began enjoying myself.

A couple days later I was feeling horny again, after getting turned down for a date. This time I decided to slip into the black panties again-after all I had only worn them a couple of hours. Then I started exploring more transgender porn. I still settled on a video with an attractive girl as well, but this time I started rubbing myself as if I were the girl.

What was happening to me?

After work the next day I decided to leave at the same time as Marina. Once we were half way to her car she turned and said, "What's up with you?"

"I've been thinking I ended things too hastily..."

"You seemed pretty decisive about it before, what's different?"

"It was weird... well, can we talk about this privately?"

"Ok, come by my place at 8:00. If you really mean it, wear panties and get a close shave. I'm tired of your games."

So after a light dinner I shaved, showered, and drove over to her apartment. The final pair of panties in the package were a pair of white ones in the same style of course.

She let me in and directed me to her small kitchen table while she proceeded to make us each a cup of tea.

After a bit of chit-chat she asked, "So what changed your mind?"

"Well, a few days ago I put my clothes in the wash and went out for a run. After I showered, I found out all my underwear was in the wash. I didn't have a single one left. So instead of wearing my gross sweaty pair again, I saw I still had the package of panties. So I put a pair on, and instantly felt turned on..."

"Interesting... continue."

I did, "And when I was looking for something to watch to deal with my situation, I stumbled across a transgender girl and a lesbian. It was really hot."

She gave a half-laugh and asked, "So what do you want to do about it? Shall we continue exploring?"

"I think so..."

"Well, you're lucky I haven't found a steady girlfriend yet. So I'll give you another chance. And while you're free to back out at any time of course, I need some assurances you won't back out just because you had an orgasm..."

"I guess that's fair. What exactly did you have in mind?"

We finished our tea. She leaned over and whispered, "Let me transform you," then she gave my ear a little kiss.

So we sat at her dresser and she proceeded to give me a make-over. She explained each step this time, but said she'd still help me if we continued. She then had me put on a bra, skirt and halter top. On the one hand I wanted to stop all of this, on the other hand I was turned on so I wanted to continue. Finally she added a wig that she said she had for when she wanted a different look while clubbing.

It took an hour, but when I looked in the mirror I looked good. Oh, I was still obviously a man with makeup and a wig, but I could see the potential.

"Now that you look presentable..." she said and gave me a full kiss on the lips. And then she took my picture.

"What?! We didn't agree to a picture of me like this. Give it back."

"Relax, its just for me... and a bit of insurance. If you run out on me again, well, some of our friends will see it. But if you want to back out and do it respectfully, then I'll delete it." I felt that was a fair deal. When I didn't protest, she rewarded me with a kiss.

As she gave me the kiss, we hugged, and my hands caressed her back down to her lovely bottom.

"Oh, so that's how it is going to be?" she asked devilishly. She stood up and took my hands and we walked together to the bed. She took off her dress and I helped her take off her bra. Marina then stuck a finger in my mouth then stuck it in her panties.

I knew what to do. She sat back on the bed and simultaneously pulled off her panties. I knelt in front of her on the bed as she spread her legs. We kissed, and I continued kissing my way down her body. I spent ample time on her breasts, then moved on to her clit, which she had already been rubbing. My tonggue was out on her button as she grabbed my head to get my tongue in just the right position. I could tell her hands on the back of my head would tighten as she wanted me to go faster and loosen to slow down. It was hard for me to do too much at once, but I did play with her nipples with one hand, alternating between them.

Her breathing and moans of exceitment peaked and her body shook as she came. After a minute, she pulled my head toward her and we kissed.

-

The next morning she texted me that she had a great time and our evening together definitely opened her eyes to possibilities with me. I replied, "Great! Can't wait to see you again."

She replied, "There is one catch: I hope you bought several pairs of panties because I want you to wear them each day for me... and I'll be checking."

If that's what worked for her, I was eager to please. Plus I kinda liked it too. I had bought the package of panties quickly because I didn't want to be in that section of the store longer than I had to be. So I sort of lucked out-it was a 5-pack meaning I wouldn't have to go to the store again. I could wear the other four, then wash and have more than half a week again.

So when I got dressed for work again Monday morning, I wore another pair of panties-this time pink. I told myself it didn't really matter, and that color might impress her. As usual, I just wore a polo (burgundy), tan pants, brown socks, and brown shoes.

It was mid-morning when Marina came to my office to supposedly discuss a project we were on. She was wearing a white and blue floral print dress. In this day of companies with open floorplans and cubicles, mine still had offices for most people. She moved a chair next to mine and set her notebook down and said in a half whisper, "untuck your shirt and pull down your wasteband." I did so revealing my pink panties. "Excellent choice, my dear. If you want to get together again tomorrow night we can, but I need you to shave your legs too."

I said, "I'll think about it..."

"Well, if you want to see me again you will. And anyway, it isn't a big deal, you wear pants every day. Plus, plenty of guys do it: swimmers, body-builders, ..."

"OK, maybe," I answered.

"Well, remember, don't back out of things too quickly this time." She said as she smiled and made a motion of taking a picture, then walked away.

As I was driving home it occurred to me that shaving that much hair might be difficult and prone to cuts, so... maybe I should use hair removal cream to do most of the work for me? And that thought took me over to the Target 20 miles away so I could quickly buy it where no one knew me. Mission accomplished.

Soon I was home and naked and applying the cream on a test skin area. Several minutes later the test area was clear of hair! It worked like a charm. So I proceeded to apply it to all of my body hair from the waste down except my pubic area. Once that was on, I had to wait several minutes. At this point I considered that I liked women with no public hair, so I applied it there too. And then I also thought I don't want hair on my back and chest, so I used it there too. By then it was time to wash it off my legs, so I started the shower and stepped in, being careful to only get my legs at first. Once that was rubbed off, and a little more time passed, I got the hair off my back and chest. I then showered as normal.

After getting out of the shower, I slipped on another pair of panties (black) and an old t-shirt. The feel of panties on my bare skin was to die for. I felt so soft. Wait, OK, what am I thinking? Society teaches any feelings like these are weird for a guy. But on the other hand, it felt good, and Marina was encouraging it so how bad can it be?

So I finished up some work, watched TV, then decided to text her a picture of me in my panties from the waist down. (I'm not stupid enough to do a face picture.) She texted back immediately "Oo-la-la" with a few smileys. Then she messaged "Perhaps you should do your chest too." And I texted back a pic of my torso. "Wow! I'll have a special reward for you!"

To be continued...