Obey Thy Neighbor Ch. 04

After I had witnessed Cecil and Li fucking I began worrying about what Chelsea might be missing out on. After all my cock was less than four inches long when erect. Seeing his massive cock penetrate Li's pussy and seeing her pussy afterward I was feeling so inferior that I almost wished Chelsea could have that type of experience. One of the reasons why I was faithful to Chelsea was my feeling of inadequacies. She was so wonderful, successful and beautiful. I soothed myself somewhat by being convinced that Chelsea was nothing like Li and would never be interested in cheating. But how would I know?

And now Li had let me in on the apparent secret that Chelsea had purchased some sexy lingerie while the two were shopping together. There was no reason to suspect that Chelsea was saving it for a special occasion for we never had done anything like that before. Then there was the fact that Li kept suggesting that I should share my fetish with my wife. She knew how conservative Chelsea was. What made her think that Chelsea would accept my crossdressing? Yet still something was not adding up. Was I missing something? Did Li want to tell me something about Chelsea? Li and I were very close by now. How much closer can you get that having a 'girlfriend' perform oral sex?

The next day in between remembering Cecil's huge cock invading Li's pussy, I wondered if I should ask Li her opinion on why I had not seen Chelsea's new lingerie. The thoughts and repercussions rolled around in my mind for a couple of days. Chelsea was still out of town when Li texted me that she needed help with her air conditioner filters. I put on panties and a bra along with spiked heels and headed through the back yard to Li's.

Li had a surprise for me. She had purchased a skirt and top combination. I tried them on and added garters and stockings. Li made me up special and had me wear a blonde wig. I told her, "That's a lot of work for coffee."

"Oh, no, Honey, we are going out to lunch."

"Li, I can't do that. I would be too nervous."

"Oh, yes you can, Millie. You look great and you have already passed the test. No one has identified your true gender so far. We are going to have lunch and come back here. I want to talk to you when we get back anyway."

Li drove and we went to a trendy lunch restaurant. The clientele was well heeled and the prices were high as you might expect. I had a salad and a glass of champagne. The waitress was very chatty and I had to use my girl voice several times. Li smiled approvingly each time. When we were alone, she complemented me on my control.

"Millie, I think we have a great start. I would like to refine you a little. You know work on your voice and such. I have some pills that will help with that. You already look passable and the medication will soften the edges on your voice. Chelsea is due back in a couple of days. I am really going to miss my little girlfriend. Do you think that there is a chance that Chelsea might approve of your fetish if you confessed to her?"

"Absolutely not. No way. She would kick me out and divorce me."

"What makes you so sure?"

"I just know how she is."

"Look, Millie. I wanted to have lunch out and ask you if you would do me a favor."

"Anything, Li."

"Are you sure?"

"Sounds ominous. What were you thinking of."

"Well, you have been a good girl and a good girlfriend the last few weeks. Would you follow me to my bedroom? I want to have oral sex with you again. You really did it for me when you sucked Cecil's cum from my pussy. I think you would really enjoy responding to my directions. So let's go."

Stunned, I followed Li to her bedroom. She indicated that I was to remove her blouse and skirt. She buried my face into her ample bosom and had me kiss each breast. She removed her G cup bra and fed me her luscious nipples. She moaned as I sucked each one into my mouth.

"Oh, god, yes, Millie, suck my breasts."

My lipstick was smeared around her big areolas. It looked so erotic. I licked between her massive boobs while she cooed and encouraged me."

She lay down on the bed. "Take my panties off, Millie. Fuck me with your tongue."

Submissive again. I pulled her panties off and threw them aside. Her pussy was dripping already. I licked her slit up and down. She moaned and held the back of my head. She kept encouraging me and instructing me to lick her. She raised her legs and had me sink further down to her asshole. I stuck my tongue in her nether opening and she shuddered. As she had her way with me, she had me lay down and she straddled my face. She pulled back her vaginal lips exposing a very had clitoris. It protruded out like a little cock."

"Suck my girl cock, Millie, make me cum."

She fucked my mouth with her clit. I puckered my lips to suck it like a little cock. It was funny really here I was sucking an engorged clitoris which was not that much smaller than my little cock. She rode my face and had me take her clit between my lips and teeth. She shouted and spilled her girl cum all over my face. My bra and breastforms were drenched as she pounded my mouth. She came and went limp. She fell back unconscious. I didn't know what to do. I lay still until finally she roused.

"Oh my god, Millie, that was fantastic. It was almost as good as fucking Cecil. I am not a lesbian by nature, but that was some of the best oral sex I have had. Guys usually don't give as good as they get when it comes to oral."

The worried look on my face told her that something was wrong. She addressed my guilt.

"Honey that is an ice breaker. You have come so far already. You are a pretty gurl and you love to dress up. The satisfaction is too great for you to resist. You have been present while my lovers have fucked me and now you have made love to me orally. I think it is time to share your secret with your lovely wife. I know it seems impossible, but couples react to one another. Ronald and I were the same when we started to open up our marriage. Now he enjoys me taking a lover. I sent him the pictures you took of Cecil and me. He was ecstatic and loved the close ups. I deleted the photos I took of you. I know we are not there yet. But you need to decide how you want to bring the subject up to Chelsea. If these things stay hidden, it could have a more devastating effect on your marriage than what you expect if you share yourself with her."

As submissive as I had become, I was now feeling that I had no choice again. Either I could come out to my wife or disobey Li. She did not practice S&M on me. She didn't have to. Once I started relaxing in my role as a crossdresser to Li, she had treated me like a girlfriend. That is what I was submissive to. It was the acceptance and the relationship. I had to find a way to come out to Chelsea.

I knew Li was not actually blackmailing me. What she said made sense on one level. I just could not imagine a conversation with my wife where things ended up well. I thought that I might leave some panties out and let her discover them. I could confess my fetish slowly and see how she reacted. Or I could just come clean with her. I thought for the next two days. Before Chelsea returned, I decided to see if I could come up with a plan to reveal myself. It was going to be a work in progress and I wanted to say the right things.

Chelsea got home and we were happy to see each other. I cooked a nice meal and served wine under candlelight. She told me how much she appreciated me taking care of her. Later in bed, we made love normally. Me on top. She did not cum. When I came at the front of her vaginal lips, most of it ran down onto the bedding. I rolled over and we cuddled.

"Honey," I said, "Sometimes I think you deserve better than me."

"What brought that on, Mel?"

"I don't know. I hear stories of women who can't get enough cock and cum over and over. I feel like I am not doing the job to help you enjoy sex. Would you tell me if that was the case?"

"Oh, uh, well, Melvin, you are plenty of man for me. You are handsome, successful, intelligent and witty. I hate to hear you put yourself down like this. I enjoy sex."

"What about orgasms?"

"Oh, I don't know. Maybe I am just not made right for that. I hear girls talk also, but I like it when you finger me."

"I know that, but shouldn't you be enjoying orgasms more? I mean, is my dick enough for you?"

"It is fine, really, Honey. I would never want anyone but you."

"Well, you know sometimes I feel so inadequate. I know you are not a complete prude. You wear nice underwear most of the time."

"Well, Honey that is how I dress under my business suits. I surely can't dress sexily in front of clients."

"Well, I get that, but I think you might loosen up a little. You are such a beautiful woman and you look so nice in your clothes."

"And you think I should wear clothes a little more risqué?"

"Oh, forget it. You look nice always."

"No, Honey, let's not forget it. I will be happy to accept suggestions on how I should dress. Li and I went shopping a few weeks ago and she said pretty much the same thing."

"Oh, really?"

"Yes, I was embarrassed, but she talked me into buying some really pretty lingerie."

"Have you worn it?"

"No. I didn't want to wear it under my business suit."

"Could I see it?"

"You want me to model my lingerie?"

"Sure, why not."

"This is strange coming from you."

"Why?"

"You never comment on my lingerie."

"Sorry. You look nice in pretty lingerie."

"Well, I am glad you notice. I did not think you did."

"So you want to show me what you bought?"

Chelsea had a little smile on her face as she went over to her lingerie drawer and pulled out a sheer thong and a demi-bra. She put them on and strutted around the bed. I motioned her over to me and touched her sexy things. They we so sheer, they seemed like second skin. Her nipples and areolas were visible under the top of the bra and her bush flowed out from under the thong.

"Li said I needed to wax to wear this."

"Yes, I can see why. Wow, I have never seen you wear anything that sexy before."

She let me feel the material. I caressed her breasts through the fabric. When I rubbed my fingers up and down her crotch, she leaned forward applying more and more pressure on my fingers. She began humping my hand until she tensed up and had an orgasm. She lay down on the bed.

"That was great, Honey." She said.

I caressed her breasts and panties. "These are so sexy and so soft. I bet they feel great."

"Well, yes actually they do. They are so light and sheer and so, ..., naughty. You must like them too. You surely paid attention to the cut and feel of the material."

"You should wear stuff like this more often.

"Maybe I will, if I get this kind of treatment."

At least the topic was somewhat on the table. Chelsea seemed genuinely impressed and happy to have modeled the lingerie for me. She had not mentioned my hairless body and I did not know if she even noticed.

The next evening after dinner, I fixed Chelsea a drink and asked her if she felt like another fashion show. She indicated that she had shown me all her stuff the evening before. I suggested that maybe we should go shopping for more items.

"Are you serious?" she asked.

I assured her that I was. Without too much convincing, she slipped on some skinny jeans and we were off to the mall. The lingerie shops were very traditional and we picked out some pretty panties and bras. We went to the shop where she and Li had shopped and the selection was a bit sexier and risqué. I helped her pick out a chemise and some crotchless panties. She could not believe that I was willing to shop much less offer suggestions.

When we got home, I asked her again to model her selections. She said that she had to do some clean up before she wore some of them. In about fifteen minutes, she came out of the bath and modeled the sheer chemise and showed her newly shaved pubis. Now she looked more like Li. I loved the look. For the first time, she let me eat her pussy. I helped her to a tremendous orgasm. When she came, she tensed up and expelled a stream of girl cum into my face. She shrieked and ran to the bathroom. When she came out, she apologized profusely for peeing in my face. I had read enough about female squirting and I convinced her to go to google later and see that this was not pee but a phenomenon known as squirting. Since she had never had that intense an orgasm before, she was completely unaware of it. I, myself, thought that it was a myth perpetrated by the porn industry.

With the advent of our newly acquired skill of her cumming and me getting her off, our sex life improved immediately. She was more loving and receptive to sex. Over the next few weeks, I encouraged her to give more modeling sessions and buy even more risqué lingerie. A big step was that she confided to Li that we were having better sex since she started modeling the sexy lingerie for me. Li told her about getting her bush waxed and from then on she was hairless. She began to love oral sex, but she would still not give a blow job. Each time she modeled the panties, I would help her take them off for sex. I began to smell her crotch in front of her and sometimes hold her panties while I sucked her off. Little by little, she started removing her panties and placing them on my face before I ate her pussy. Once I poked my head through the leg hole of a thong and wore them while we made love.

After she came, she looked at me and said, "Oh, Baby, you look good in my panties."

"Really?" I asked. "How about I put them on?"

"Suit yourself, Honey."

I timidly took the panties and pulled them over my feet and up my legs. My little cock made a small outline in the tight fabric.

"I can see why women wear these. They are so comfortable."

"If they are that comfortable, why don't you leave them on?"

I pulled the panties up tighter. "I think I will." I said.

"Well, you certainly are cute. And just my size. I guess I won't have to worry about you stretching the elastic, huh?

When she lay beside me, I pulled her hand to my little cock and she began rubbing me through the sexy panties. I was so hard. As she stroked the outside of the material, I shot a huge load of cum into the panties. Chelsea looked at me amazed. "Oh, my god, someone else loves the feel of my sexy little undies."

That was the start of my journey into crossdressing with my wife. She saw how horny the panties got me and soon as she modeled the panties, she would do a striptease and then put her panties on me. I always came in them. Sometimes I would suck her to one or more orgasms. Even if I came first, I still could bring her off several times with my mouth. Generally from then on, we seldom had traditional vaginal sex. I knew my little cock did nothing for her. When I sucked her, she came like a starved prisoner.

I did not tell Li anything about our sex life. Chelsea was due to go out of town again. The night before she left while she was packing I saw her filling her suitcase with her regular lingerie. I stopped her and asked why she didn't pack some of the new things.

"Are you kidding me, Mel? Who is going to know anyway? Besides, I like the attention I have been getting with you."

"Well," I answered, "If these things make you feel sexy, you would feel sexy while you are gone. Besides you might find a man who would love to enjoy the sights of your beautiful body in lingerie as much as I do."

"Very funny." She said.

"No, I am serious. I bet you get propositioned all the time. You could wear some of these things under more casual clothes while out at night. Shopping, dining, the cinema."

"They still would not show under my clothes."

"If you wore more revealing clothing and someone just happened to see. Like up your skirt or maybe down your blouse. Who knows, you might attract a man with a big cock."

"Ha, that sounds like Li. She has been telling me about her arrangement with Ronald. Did you know that she has lovers on the side and Ronald approves?"

"What, how would I know something like that?"

"Yeah, I guess you are right. Well, now you know. She tells me about her lovers' big cocks."

"So I guess you are envious?"

"No, are you crazy. I would never cheat on you."

"Well, from what you say, Li does not cheat on Ronald, either. If he knows and approves."

"Wow, so what are you saying?"

"Just pack some of the sexy things and buy some casual clothes that are more revealing. You will see immediately what that does to men. Maybe forget your panties when you go out to eat and wear a short skirt. Maybe Mr. Big Cock will find you."

"Are you serious?"

"Just wear some sexy things out and give it a try. Tell me about it if you notice anyone with his tongue hanging out. Tell you what; leave your regular panties here. They are very nice. I will wear them while you are gone. If something comes up while you are dressed in your more sexy ones, how about saving them in a baggie and bring them back home. You can put them on my head while I service you orally. You might even come home with cum in them. Wouldn't that be funny if you placed your cum stained panties over my head when you got back?"

"You are trying to be funny. And you will wear my regular panties while I am gone?"

"Yes."

"Why?"

"Because they feel so soft and sexy and I will be thinking about your shaved pussy when I wear them."