A Brother's Memories Part 4


She said that she had always found the sight of him in his panties and other sexy things made her so hot that they would make love for hours. One time she even asked if she could see me in panties. Since we were alone I agreed and closed the door. With my back to it so that no one could walk in on us I proceeded to drop my jeans. Marge was about 3 feet away as they slid down my legs. It was exciting to have her want to see me in her/my panties, and my dick was getting very hard as she stood there staring at it.

"Well Richard," she said, with a cough, "That is a real nice package you have there. I would love to feel it, but I have never cheated on my husband, and I am too old to start now. Thank you for showing it to me! Now, if you don't mind, pull your pants up and get out of my way because my husband is about to get raped!"

"Yes Ma'am!" I replied with a salute. I pulled up my pants and Marge grabbed her basket and headed out the door. As she passed me, she stopped and gave me a little kiss on the cheek, and with a smile she was gone. I hope her husband was up for it.

Shortly after that day, I got another job, as an electrician. Since I was gone almost every day I only rarely got to see Marge. When we did meet, it was as a couple of old friends, we never mentioned that morning. She even introduced me to her husband, Roger. She had asked me not to let on that I knew about his hobby, but from the way he greeted me I knew that she had told him about mine! Well, it was all right by me if it gave them pleasure.

I didn't have many opportunities to indulge in my hobby anymore. It always seemed that I was never home alone anymore. I did get to wear my panties to work occasionally, but only if I knew I was going to do the next load of laundry. However, getting a day off, during the week was almost impossible. Then, around Christmas time, Betty said that she really wanted to spend a couple of weeks with her grandparents up in Northern Oregon. I tried to get time off, but the boss said that the new person holds down the shop during the holidays.

Betty left on the Friday before Christmas, and was due back in two weeks. The first night she was gone, her mom, Edith, and step-dad, Duane, invited me over for dinner and to play some cards. We have always gotten along great. Her mom is one hot woman and Duane is just a good ol' boy. They have a bar in their living room and don't go out much. We sat there and tried to kill the keg of beer in the bar. We didn't succeed, I passed out on the couch sometime after midnight. They had covered me up and went to bed.

I awoke sometime later to the unmistakable sounds of two people making love. From where I was sleeping, I could see through their bedroom door, which was wide open, and see that Edith was impaled on Duane's cock and was enjoying herself immensely. She was in profile to me and I had a wonderful view of her as she rode his cock. I was hard in an instant and was reaching for my cock when I remembered where I was, and that I had taken the opportunity to wear my panties. I didn't think that they had left their door open as an invitation to join them, but just for the thrill of performing for another. I was about to get up and quietly leave when Edith turned, and looked me in the eye and smiled. She held the gaze for a moment and then turned her attention back to Duane.

I eased off the couch and let myself out the door. It looked like it was near dawn as I headed back to my apartment. I had a raging hard-on from the memory of the look that Betty's mom had given me, as well as from the look of her making love. I let myself in the apartment and closed the door and dropped my pants, whipped my cock out, and proceeded to stroke it to a very satisfying orgasm. As I headed for bed I realized that I was alone and had two whole weeks to indulge myself. I went to Betty's under-ware drawer and got a pair of her satin panties. They were a cobalt blue and I had always loved the way they made her look. I was about to climb under the covers when I thought about the matching chemise hanging in the closet. I hoped it would fit, and it did. It felt so nice against my nipples. I slid into bed and let my hands roam over my satin covered body. I felt so sexy that I drifted off to sleep with one hand rubbing my cock through my panties, and the other rubbing my nipples.

The sound of a door closing is what woke me up and I laid there for several minutes trying to identify the sound that had disturbed my slumber and luxuriating in the feel of satin against my skin. I needed to get up and go to the bathroom and get rid of some of the beer I had drank the night before so I swung my legs off the bed and headed for the bathroom. When I had taken care of my business I headed for the kitchen to make some coffee. There was a thermos and a white sack on the breakfast bar that had not been there last night. I peeked in the bag and found a cinnamon roll, along with a note:


Stopped by to see if you wanted to go to breakfast with us this morning, but you were sleeping so soundly that I decided to let you sleep. Brought you some back though, I hope you enjoy it when you get up.

Thank you for being such a gentleman last night, we were just a little out of control.

I found your clothes by your front door when I came in and I put them in the hamper for you, and I really do thank you for the fine compliment you left me.

Love Edith,

PS: I think your outfit looks sexy, it will be our secret, and enjoy your day off.

I remembered my masturbating at the front door when I came in and probably should have been embarrassed about being found out. Somehow I couldn't get worried about my future mother-in-law knowing that I thought she was sexy or what I had been sleeping in. I was feeling too good to be upset so I poured a cup of coffee from the thermos and took it, along with my pastry, to the couch and proceeded to spend the entire day right there, dressed in Betty's panties and chemise.

It was a very enjoyable two weeks. I wore a different pair of Betty's panties to work every day. We had agreed to have our Christmas after she got back so I went a little crazy shopping for her. I did a lot of it the week after Christmas and was able to buy her several complete sexy outfits. Edith helped me wrap them and made several comments on my taste. Edith, Duane, and I celebrated Christmas Eve together, we had a delightful dinner and after dinner drinks, then we gathered around the tree and exchanged gifts. Later, as I was leaving, Edith gave me one more present and told me that I should wait to open it after I got home.

When I got home and opened the gift I was blown away. It was a very expensive iridescent -blue outfit with white lace trim and accents. It was the entire set with, panties, chemise, garter-belt, stockings, a short gown, and a long one, plus a full-length robe. I looked at the card and it was signed from the both of them. I took a bubble bath and then dressed in my new outfit. When I looked in the mirror it was like looking at someone else. I was about to call and thank them, when they called me to see if it fit ok, and if I liked it. I told them it fit perfectly and that I loved it. Edith told me that they both picked it out and were glad that I liked it. I was wearing it that night when Betty called. She was lonely and depressed that we weren't spending Christmas together. She told me that she never wanted to spend another Christmas apart.

Chapter Nine:

April arrives, with many surprises

It was during the next week that I first experimented with one of her vibrators. We often used various sex toys in our lovemaking and had several to choose from. I was laying there in panties and a bra. I was imagining what it must feel like to be a woman and have a cock in your pussy. I reached in the nightstand drawer and took out one of Betty's smaller toys; it was about 6 inches long and 1 ½ inches thick. I started running it around my cock and balls. It felt nice and I was enjoying myself, so I pulled the crotch of my panties aside and slid it down my crack. I was dry and it didn't feel that good so I got some lubricating cream and tried it again, and this time it felt much better.

I began probing my ass, placing the tip at the opening and rotating it around with just a little pressure. I could feel my ass relax and open up a little so I increased the pressure and was rewarded as the head slipped in. I let it rest there for a few minutes, just enjoying the feeling of it vibrating against the walls of my ass. I slowly increased pressure and it slid deeper inside me. My cock responded by getting harder and started throbbing in time with my heartbeat. Finally I pushed it all the way in and held it there, as I grew accustomed to the pressure it was exerting on my insides. I began to stroke it in and out of my ass, as it came out I felt the void it left behind collapse, then fill again as I pushed it back in. If this is in any way what a woman feels when they make love that I do envy them their sex.

I began pistoning it in and out of my ass as I stroked my cock in the same rhythm. I was bucking my hips trying to get more of it inside me. The combination of my thrusts and the vibrations of the dildo had me on the edge of cumming. I began rotating it deep in my ass until I stimulated my prostate with the vibrating tip. There was no warning or anticipation of what was about to happen; I just started cumming in buckets all over myself. It was so immediate and powerful that I wasn't even sure what triggered such an intense orgasm, but I knew that I wanted to feel it again.

You might think that in finding this side of my sexuality that my relationship with Betty would suffer; just the opposite is true. I have found that I am more attuned to her wants, needs, and desires. I can better anticipate when something I am doing, or am about to do, will cause her anxiety, concern, or unhappiness. I found myself even more intent on pleasing her emotionally and physically. I tried to become more romantic, considerate and even a better friend. Our lovemaking has become more intense and more frequent.

This was the status of our relationship on that fateful day, the day that I took the next step in our relationship and my life. I had the day off, and as usual, I was enjoying some quality time with myself. When she came home early and caught me, dressed in a pair of her silk panties and bra and one of her vibrators up my ass. I had just shot my load and was licking it from my hands when she cleared her throat from the bedroom door. I had been so intent on my pleasure that I had never even heard her come in. At first, I thought she was going to freak-out, I started to try and explain, to her, but what could I say? Then she started to smile, in a very mischievous way, and get undressed.

She joined me on the bed and started to play with me through her bra and panties. I usually need a long time to recover after I come, so I was amazed when I started to get hard all over again. She reached down and grasped the vibrator, which was still buried in my ass, and began to fuck me with it. She was gentle and loving as she drove me to a peak of desire, and when she had me ready to go, she suddenly got up, got dressed, and left the room. I just knew I was in for it. I heard her make a call but couldn't make out what she said or whom she had called.

When I realized that she wasn't coming back I got up and went to take a shower and clean up. I hoped she would not make a big deal about my hobby. While I was in the shower, the door opened and she was standing there in her bra and panties, holding my shaving cream and razor.

As she stepped into the shower she said, "If you really want to wear my good underwear and look like a woman then you really need to lose some of that excess hair and have it done right."

I thought what the heck and replied, "Sure, if you could help me."

Leaving her underwear on, Betty stepped into the shower, "I'll help, but you need to do this my way. I know what to do and you will just have to trust me, ok?"

As my cock began to harden again, I replied, "Anything you want dear."

"You did look really sexy when I walked in on you, but when I get done you are going to be a fox! We don't have a lot of time so no fooling around! Now raise your arms."

She began with my armpits and began to shave me everywhere that needed it. My chest, groin, legs, and even my ass. I am not a very hairy guy and it didn't take long. The feeling of her slowly shaving me, and the fact that she was partially dressed and unavailable was a double turn on. After she was done she told me to get out of the shower and double shave my face while she took a shower herself.

Just as I finished shaving, the doorbell rang. Betty asked me to please answer it. I put a robe on and went to get the door. It was Betty's best friend and co-worker (they worked as property managers at a big apartment complex), Lorie. She had several bags with her and asked if she could come in. While she waited in the living room I went to tell Betty that Lorie was here. She met me in the dressing area naked and from the looks of her pubes, freshly shaved. Her nipples were really hard and rosy. She said that she knew that Lorie was here and that she had called her to have her bring a few things over.

I didn't know what was going on and I guess I looked a little worried. Betty said that it was a real turn on to see me dressed in her sexy things. I should say that we had often fantasized about a threesome during our lovemaking and it had always led to some fantastic sex. She started took my robe off and started to put some body powder all over my body, it felt incredible. I tried to remind her that Lorie was out front when a voice behind me said no she wasn't. I turned around and there was Lorie standing in the doorway in just her bra and panties. I was shocked but still game. She walked over to Betty and kissed her deeply and held her tits and the sight of her and Lorie kissing renewed my passion. They had me sit at the mirror and told me that they were going to have to go back to work later and would like me to come with them as a co-worker. A woman co-worker!

Lorie went and got the packages from the living room and had me open them. In the first, I found a pair of red silky panties, in a size that should fit just right, also a pair of panty hose, a loose skirt, blouse, and shoes. In the second was a matching bra, and I mean to tell you it was an industrial strength bra. I had been wearing Betty's flimsy little bras and of course my breasts never filled them. Betty assured me that it might look formidable but when they were done I would love the effect it would have on my figure.

Well to make a long story short, they spent about an hour and a half working me over. The began with my makeup, and nails. I was amazed at the transformation happening right before my eyes. Next came my panties and hose. The hose were control top and helped to control my dick which kept getting in the way. I was so excited the whole time but they wouldn't let me touch them or myself the whole time. Every once in a while they would pause their work to fondle each other or give my breasts or dick a tweak. I was in heaven. I couldn't believe that all of this was happening.

Next came the bra! It had a wide band under the cups that was a little constricting and the ladies had quite a time getting it hooked. Then they began reaching in the pitifully filled cups and pulling on the skin along my sides and pinching and pulling and all sorts of things. They slipped some pads in the cups of the bra and all of the sudden I noticed that I had cleavage. It really looked like I had breasts. I put my hands under them and squeezed, they felt about right, a little stiff but ok, They were about a 'B' cup and kind of spilled over the top, just enough to be kind of sexy.

They finished dressing me and then Lorie went out front and got another bag and pulled out a wig and put it on me. I really looked the part of a slightly overweight woman. The only thing really wrong was the fact that my dick had gotten hard and was sticking straight out, even with the pantyhose. Both Betty and Lorie looked down and told me that they would have to take care of that, they went to there knees and took care of it really well.

With my now soft dick tucked in my pantyhose, the women started getting dressed for work. I sat there and marveled as they told me some of the things that go on at work. You will get an idea when I tell you what happened to me that night. Neither of the women put any under-things on and had on short skirts and loose fitting blouses. After one last check we left for the complex where they worked. Just three of the girls, Betty, Lorie, and April, (the name I chose for myself).

When we arrived, the office was locked and there was a man Brian, waiting to see one of the apartment units. The two women apologized for being late for their appointment. He said that was okay, he wondered whether they were ready to show him the apartment now. We took him to see the unit he was interested in. It was a garden cottage at the back of the property, very secluded and romantic. I had a good idea why Betty and Lorie were always #1 and #2 in rental performance. Betty bent over a little as she unlocked the door and I could just see a hint of her butt as the wind gently moved her skirt, I was sure that Brian noticed as well. I walked behind the three of them as we entered the unit and Betty began explaining the benefits of renting in this complex.

While Lorie took Brian to show him the kitchen, Betty went out the glass patio door to the garden and bent over to smell a flower. Her bare ass was open for view and her pussy lips were all red and swollen. I was just standing around and feeling uneasy that I was going to get found out. Betty motioned me to come out and join her, and when I did she put her arm around my waist and hugged me.

"Are you ok with what is happening?" Betty asked in a whisper.

"I'm just worried about getting caught."

"If you just follow our lead then everything will be fine and you might even get your wish."

"What wish?" I asked.

"The wish where you watch me have sex with a complete stranger."

"Have you two done this before?"

"Yes we have. Does that upset you, or does it excite you?"

"It excites me very much my, love."

"You know that it is probably going to end up with someone getting fucked tonight so be ready for anything. Now, here they come, squeeze your legs together, so your dick won't show, and bend over and let us show Brian what we've got!"

Brian was telling Lori what he thought about the kitchen when they came back into the living room. I could tell exactly when he noticed us on the patio because he stopped in mid word. Betty reached over and began rubbing my ass through the pantyhose.

Betty whispered, "We are going to stand up now, but you need to keep facing away because your cock is sticking straight out. I want Brian to think that you are my lesbian lover, while I fix it for you, so just follow my lead."

Betty stood up and moved behind me, and began rubbing my sides and kissing my neck. This was not going to do much good to make my dick go down, it felt much too good. Then she reached her hands around me and cupped my breasts. She let her hands move down till they were almost touching my cock. She began pulling my skirt up till it was bunched around my waist. I looked down and there was a wet spot growing on my panties. Betty slid her hands down inside my panties and repositioned my cock so it didn't show. She let my skirt slip back into place and told me to turn around and kiss her.

As I did so, I could see Lorie had her back to us and Brian was staring over Lorie's shoulder at the show that Betty and I were providing from the garden. I could see his dick growing in his pants as they had started to tent visually. Betty slowly broke the kiss, turned, and walked into the room. I followed, keeping her between Brian and myself because I still wasn't sure I didn't show.

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