April is born
Chapter 2: April arrives, with many surprises

Copyright© 2001 by Rich and Monica

Erotica Sex Story: Chapter 2: April arrives, with many surprises - Richard gets his first taste in the joys of women's clothes.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Ma/Ma   Consensual   Romantic   BiSexual   True Story   Group Sex   Sex Toys   Transformation  

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 1/2 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.

 
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