Obey Thy Neighbor Ch. 02

In the first few weeks after Li had discovered my crossdressing fetish, I worried constantly about her changing her mind and telling my wife about my activities. However, the more time I spent with her, the more confident I became that she was genuine. Since Li's husband, Ronald, was hardly ever around we were in very little danger. Even if my wife, Chelsea, came home early from a trip, it was unlikely that she would go to Li's without calling her first. I felt more and more at ease dressing in front of her. She definitely had a darker side than anyone could have imagined, but I was not one to talk.

Chelsea is an accountant and very dedicated to her work. We both make very good money, but we have to sacrifice our time together. Our plan was to work hard early and reap the rewards later in life. It is not like we did not enjoy ourselves; we just spent a great deal of time apart. I had tried to loosen up Chelsea with sexual humor, but after time it became evident that she was not appreciative of this banter. I continued to feel guilty about my masturbation and crossdressing, but I accommodated my tendencies by reminding myself that I was not like some men who sought the company of other women. Guys tend to blame the wife in order to do what they want anyway. In that respect I guess I was no different, but it seemed quite minor compared to cheating.

I had never had any reason to suspect that Chelsea was cheating on me. In fact, just the opposite. I had indulged in some fantasies where I imagined her fucking other men while she was out of town on business. When I travelled, I would read stories about cheating wives and imagine her getting fucked by a really big cock. I mean it bothered me some that my own cock was so little, but it wasn't a burning insecurity either. I was successful in business. I worked hard to provide as did Chelsea. A little fantasy was my only vice. When I started dressing in her lingerie and later bought my own, I considered it totally apart from my wedding vows. Chelsea never seemed to indicate that she was unsatisfied with my sexual performance.

The first test when Chelsea came back from her out of town assignment was to see if she would notice that all my body hair was gone. Being of slight build, I never have stood out in a crowd. My hair is a very light brown anyway. You might even call it dishwater blonde. My chest hair is very minimal, hardly noticeable so I stood a good chance that Chelsea might not notice. My pubic hair on the other hand would be a problem when we had sex. Since Chelsea is not into anything remotely adventuresome, I managed to have sex with her a few times before I had to take a three day trip out of town. I had made sure not to put myself into a position where she could discover my panties. I could not chance wearing a bra even though Li had told me to. I would just have to face her if she questioned me. I had my bags packed with panties, bra, nightgown and pantyhose for my trip. Li knew that I was to be gone. She came over for drinks the evening before I left.

When Chelsea went into the kitchen, Li looked at me and made a slight gesture to her breasts. I knew she was asking about the bra. I shook my head and she smiled. It was a very subtle but significant type of communication. It did tell me that she understood and was not going to force the issue. That was comforting at least. Li asked Chelsea if she wanted to go shopping one evening while I was out of town. Chelsea tentatively agreed and Li said, "Great. I want some new lingerie and you can give me some ideas on what you think is sexy."

Chelsea seemed not to pick up the innuendo and almost blushed when Li said it. It was not totally out of the ordinary for them to go out together, but I doubt if they had ever been lingerie shopping together. As I stated, Chelsea is not a complete prude and she does dress in nice lingerie. However, hers is more functional than really sexy.

While I was gone, I picked up a light lace bralet to sleep in. I wore a long thin sexy gown and the material felt great on my hairless body. I had not removed any more hair and I was beginning to show stubble, but I was afraid to press my luck.

I got a text from Li, but it was not asking for help. She let me know that she and Chelsea had a great time shopping. She told me that I might be surprised when I got back. It seems Li talked Chelsea into buying some pretty panty and bra sets. I had to be careful not to let on when I talked to Chelsea. Of course I deleted all the text messages as soon as I read them.

Chelsea did not mention anything about shopping with Li when I returned home. We talked about our upcoming schedules. I had plenty of home office work stacked up from my business trip as well as some things I had to catch up on. Chelsea was in town for the week so I expected some us time and thought that I was clear with Li. Apparently Chelsea had told Li our schedule because around nine am, she texted me about her air conditioning filters. I got dressed and stepped through the fence. As soon as I got inside her back door, she had my stilettos and duster gown ready to go with my bra and panty set. Luckily I was wearing suntan stockings and a matching garter belt. Stockings and garter belts to me signify more than just functional. They signify sex. My cock was hard and poked into my bikini panties. Li smiled at me once I was completely done. We went over to her breakfast nook and she poured us some coffee.

"Millie," she said, "Chelsea is going on two more long out of town trips in the next couple of months. I think we should spend some time with your new persona."

I had no idea what this meant, but was sure I was about to find out.

She outlined a plan for her to go to a very upscale wig shop. She was going to get me two wigs. I tried to tell her that it was a bad idea. I had too much work to do and could not spend much time that week. She said that was fine, she just wanted to let me know. My reluctance had no impact on her and she talked about neighborly things for a while. She knew I was busy so she told me I could go back and knock out some work.

"Chelsea show you her new things yet?" she asked.

I was wondering about this and why Li was making an effort to keep me informed. And yet Chelsea had not mentioned anything to me. Li did not seem to be prying, just curious. Anyway it was not like Chelsea to dress provocatively so I wondered what she had purchased. I told Li that she really didn't make a point of showing me her new clothing. Sometimes I would notice and compliment her on a particularly attractive dress or shoes, but never lingerie.

The next day Li called me and asked how my work load was going. I told her that I was catching up quite nicely. She said that I should try to schedule as much time at home as I could when Chelsea left on her two week trip to San Francisco and Los Angeles. Chelsea was combining some client visits and to save expense money, she was staying in California for the whole trip. I arranged to get as much work done ahead of time. In addition I took a whole weeks' vacation time. Li knew that I never took any days and she thought it would be a great time to devote to Millie.

I took Chelsea to the airport on Sunday evening. We made love the night before. Chelsea still made no mention of my pubic hair being gone. Monday morning Li texted me about her air conditioner filters. She told me to just wear a robe through the secret passage. My hidden stock was for daily wear and the real sexy stuff was with Li. When I tapped on the door, Li had coffee ready.

"Okay, Millie, we have a thousand things to do today. Let's go into the master bath and remove all that stubble."

She watched as I used the crème and the razor. By the end, I was completely hairless except for my eyebrows and hair. Since my hair is so light, my eyebrows are very light. Li plucked them into a more feminine line and remarked how easy it was to blend back in. I knew where this was heading. She placed a nylon cap over my own medium long hair and proceeded to apply eyebrow pencil, eye liner and mascara. When she added the eye shadow, I was shocked at how large my eyes now looked. We had been leading up to this point and I made little fuss about not wanting her to give me my first makeover. My male features are soft anyway and highlighting the positive as well as disguising the negative made me look like a whole new person. When she added the base and spray powder along with the shadow to my cheeks, I bore no resemblance to Mel. I was Millie. She pulled a light brown wig over my cap and added clip on earrings.

I had my robe back on at this point. Li instructed me to take it back off. My little cock was hard. I was used to Li seeing me almost naked by now and she always ignored my hard little cock.

She gave me my bra and panties to put on.

"This time, Millie, we have to do something about that little clit of yours. She had me sit with an ice bag in my crotch for about twenty minutes while she primped the wig and added touches to my makeup. When she took the ice away, my little four incher was about an inch long. She giggled and had me tuck the little fellow under my scrotum. My testicles were up in my body cavity. Li taped the scrotum over my pushed back little cock and had me slip into my panties. They were too tight and I protested.

"Stop whining. It is a gaff panty. No one wants to see that little thing poking out of your underwear, Dear."

She let me wear pantyhose and had me slip into the crème colored stilettos. Even with the high heels on she towered over me. Her full figure contrasting to my slender lines made me look like her little sister. I slipped on my house duster and we were now pretty girlfriends. The relationship changed almost immediately.

"Millie, I can't get over how good you look. Your legs were definitely made for a woman. That will get you through most of the situations when we go out. We just have to get a little girdle to hold your new hip flesh so you will fit into pants and skirts. Your face and breasts already look great."

"Uh, Li, I was not planning to go out dressed this way."

"I know, Sweetie. But we are ready to expand our horizons some. You see Ronald and I have a sort of arrangement. I mean I rarely see him. He is so busy around the country and it would not be fair to either of us to remain monogamous. We just keep it very private and do not make a big deal about it. In fact, we text, snapchat or facetime each other all the time when one of us gets lucky, so to speak. Now Ronald will never know about you, Mille, because after all, you are my new girlfriend not a lover. However this is so wonderful having you that I want you to spend some time with me and some of my friends. You know male friends. They will never know who you really are. In fact they may never know that you are not a girl genetically. Based on how you look to me now, you are very much a sweet lady. You need to get some confidence about your alter ego."

This was starting to get a little too much. She expected me to go out in public dressed this way. I had to draw the line somewhere. What if someone I knew saw me out in public dressed as a woman? After looking in the mirror again, I did wonder whether some casual acquaintance might be able to recognize me. I looked so different as a girl. My little cock was starting to get hard just looking at myself.

Li and I tried on some clothes. She told me that the next afternoon she was meeting one of her 'friends at a hotel downtown. She said to come over to her house around noon and we would get dressed. I was a nervous wreck starting at that point. I could not muster up the courage to tell her no. She had me take off some of the clothes and put on my gown to go back home in. I wore my heels and tip toed through the patio and back yard. As always I was careful with the fence gate so as not to snag my lingerie or gown. I got a drink and went about some work. I hoped like heck that no one came to my door while I was made up. I took my makeup off before I went to bed. I could not afford to soil the sheets. I pumped my little cock inside my panties and came before I went to sleep. The sheets would have to be changed the next morning.

At noon I tapped on Li's back door. I had worn panties and my pocket bra. I wore the wig even though we had to restyle it. Li did my makeup actually very conservatively. She placed a darker wig on my skull cap and primped it up a bit. She had me slip on a French Maid's dress with black stockings and matching garters. I was already wearing hot pink lipstick so she did my nails in pink polish. She had tried to get me to get a manicure and fake nails. I could never explain that to anyone so I resisted. I wore her trench coat over my dress, but my legs and heels still showed plenty. In the parking garage at the hotel, Li told me that she would text me soon with the room number. I was to go directly to that room and tap on the door.

"Now, Millie, just act natural. Pay attention to your walk and don't plod. Take smaller steps and look people in the eyes. I am going up and tell Tommy that we have our own maid for our little afternoon delight. You will not have to participate. Just help me get ready for him and maybe have some wet towels for us when we take a break. He has a big cock. Not the biggest but still plenty for me this afternoon. You watch how he fucks me and remember you are not my neighbor Mel anymore, you are Millie. This is a good step for you. You might pick up some pointers. I mean with your little cock, you should really have some special technique to keep Chelsea satisfied."

I waited and got a text about ten minutes later.

COME UP TO ROOM 1657 AND TAP ON THE DOOR QUIETLY. WE ARE WAITING.

I walked into the lobby and tried to remember everything Li had told me. Against my natural inclination I made eye contact with people walking the other way. Most people did not pay that close attention anyway and eye contact would be avoided unless you were interested in talking to the other person. It was a good tip because it focused attention on my eyes and they look fabulous. Along with my slender legs, the eyes and makeup were my best feminine features.

After getting off the elevator, I tapped on the door. Li opened it and let me in. She took my trench coat and there I stood dressed as a French Maid.

"Tommy, this is my girlfriend, Millie. Millie, my good friend, Tommy."

Everyone said their 'pleased to meet ya' hellos. Tommy was dressed in slacks and a sport shirt. He was around thirty or maybe late twenties. He was well built but not muscle bound like some of the gym rats. He had short blonde hair. I don't know if he knew Li had a son in college or if he even cared. With her tall oriental features softened by the European heritage, she was more than equal to any woman younger or older for that matter.

Li indicated that I was to help him with his pants and shirt. I let him remove them and dutifully hung them on hangers. He stood there with only a lime green thong on. His cock was hard and bulging the front of his thin thong. Li took her overnight bag and stepped into the restroom. I followed and helped her with her lingerie. She wore a red teddy with panties. Simple and to the point. Her huge breasts stood the top out away from her body and made a tent of the whole top. Her pussy was completely smooth and her vaginal lips were fluttering out. I could even make out a bulge in the clitoral sheath at the top of the vaginal lips. It was a very pretty pussy. After pulling on the teddy bottoms, she walked out of the restroom indicating for me to follow. I poured them some champagne chilling on the bar. Each took a sip. They handed me the glasses and Li snuggled up to Tommy. They kissed and explored each other's bodies. Li's areolas puckered and her nipples hardened. The teddy was so thin I could see straight through. She ran her hand up and down his cock and cupped his big testicles into her palm. This stretched the thong even more. What a package.

Li moaned as she felt the long thick cock up and down. Tommy pulled her top off and feasted on her wonderfully full breasts. As he sucked one and then the other nipple, they were about a half inch long and hard as pebbles. Her areolas were soft pink probably due to her European heritage. Such beautiful breasts on such a tall dark beauty were just too much for any one woman. She is gorgeous. Tommy then pulled her panty off and licked her pussy. As he rose up, I could see the glistening coating on her butterfly like vaginal lips.

"Millie, help Tommy with his panties, please."

Tommy lay flat on the bed and watched as I kneeled in front of him and touched each side of the thin elastic band. His cock was already leaking precum and I could make out the full outline. I tugged the thong over his hips and out sprang the most beautiful cock I had ever seen. It was as thick as my wrist and about nine inches long. He was as smooth under the waist as I was. However his big almost grotesque looking cock was completely different than my little thin stem. I took the thong over to the nightstand and folded it neatly. Li sank down and got on all fours above him. She took the tip of his cock in her red lips and licked the head. Slowly she pushed her mouth further and further down until she was about half way. She pulled back up and licked the underside all the way to his huge balls. Again she took him into her mouth and plunged further down. She did this a few times until she took him all the way down her throat. She then licked the underside of his cock and balls with her tongue. She pulled back and coughed. A huge strand of saliva and precum followed her mouth and streamed away from his cock.

She savored his fullness and then took him again into her throat. I marveled at how much skill it took to sink that cock all the way past her gag reflex and down her gullet again and again. Tommy moaned.

"God, Li, don't make me cum. I want that sweet pussy. I want to cum in your pussy."

Li pulled off his cock. Her makeup was a mess. The effort it took to deep throat that monster cock released all of the tear ducts and nasal sinuses. She had saliva all over her face. She rose up and placed the shiny wet cock to her vagina and in one step plunged herself down on the massive shaft. She fucked him cowgirl and rode him like a bronco. She was moaning and he was groaning. Tommy reached for her hips as she pounded his cock into submission. She was fucking him so hard that I marveled at his staying power. He finally succeeded in slowing her hips down and they settled into a slower deep rhythm. Tommy was now thrusting his cock into her as she leaned over and rested her big breasts on his chest. This was the most erotic thing I had ever seen. Her tit flesh was squashed against his chest and boobs were rolling out each side of her underarms. She reached up to his mouth and stuck her slippery tongue into his. They fucked like this for a good while until Tommy started getting a little irregular in his rhythm.

"Ready to blast your load in my pussy, Tommy?"

"Oh, god, yes, Li, FUCK ME HARD."

Li bounced back up and began grudge fucking him again. She rose almost all the way off his huge cock and threw herself time and again down on the hard shaft. She seemed out of control and came in gulps and sighs. She tensed up, had an orgasm, and then bounced again. She must have had five orgasms one right after the other. Finally Tommy bucked his hips and raised his butt off the bed taking Li up with him. He was deep in her pussy when he began shooting his semen into her. I thought she would be immediately impregnated. They stayed like this for a long time. She established a rhythm again and I noticed his cum running out around his plunging shaft. Finally she rolled off him. He lay on the bed with his huge cock starting to soften slightly. His cock was a mess with the remnants of his huge load coating it and the cum running down his balls and pubic area.