My Friend Ashley Ch. 04

In a few short months, I had gone from a broken-hearted little man with a small dick to dressing as a woman and having oral sex with women and one man. What really stressed me after our date with Kevin was that Gretchen had instructed me to suck Kevin's big cock and I had acquiesced without so much as a second thought. Afterwards, I had trouble deciding whether it was the thrill of watching my bi-sexual friend having sex with a big black man, or me kissing and sucking his cock myself, or eating his cum from Gretchen's pussy. Somewhere in the deep recesses of my mind I thought I was supposed to feel guilty about what I had done. But I did not. Sad to say, I had felt just as happy after this type of sex as I had when I had actually fucked Ashley and Gretchen.

I didn't feel gay, either. I thought that dressing as a woman and sucking a cock surely made me gay, but I still did not feel this way. Gretchen told Ashley about our little tryst with Kevin. By now Ashley was convinced that I was not just being led around by the dominant Gretchen. Ashley asked me a few nights later about the date.

"It is really strange, Ash. I don't know what is happening to me. Before I moved in with you, I was a mess emotionally over breaking up with Karen. Now, I think I should feel even worse. I mean, participating in oral sex after you had vaginal sex. Sucking my cum from you after we had sex. Sucking Rod's cum from your vagina after he fucked you. Sucking Kevin's cum from Gretchen. And not to mention, actually sucking Kevin's cock when Gretchen just motioned for me to. I guess I am gay after all."

"You just described sexual freedom, Dummy." Ashley said.

She continued, "Do you want to have an emotional relationship with either Rod or Kevin?"

"No. That is what puzzles me."

"Ra'Chelle," she said, "You are not gay, but you are a submissive. Both Gretchen and I are strong willed and dominant women. We are different in our own ways, but somewhat alike. You are comfortable with both of us because we buffer your preconceived notions of sexuality. It is more pleasurable for you to go along with what your typical male self would find abhorrent, rather than to lose your relationship with either of us. Well, don't worry about losing anything. It is not like you lose a possession. That is why it hurt you so much when Karen left you. You felt like you were losing something. You have to own something to lose it. You don't own someone and we don't own you."

She continued, "I think that the sexual experiences you have had after you and Karen broke up have made you realize that your sexuality is actually more than what you have sexually. To me it is a way for you to come to grips with your, uh, under-endowment. Comparison to peers has caused you to have inferiority issues. I don't know how much you will change after this, but you are coming to grips with your perception of yourself."

"That's some heavy shit, Ash."

"Yeah, I know. I was afraid to even mention it to you. However, you seem to have enjoyed the three-way date with Gretchen and Kevin. Fuck, it makes me hot just thinking about it. I suggest that you not deny your perceived shortcomings but embrace them. I think I have a solution for you. Instead of trying to hide your little dick, let's try to emphasize it. I would love making you up as my girlfriend like Gretchen did. I think I am enjoying more the idea of you as my lesbian girlfriend after what Gretchen did to me. I was a victim myself of what I described to you. With all of us participating in that strange three way, I was actually more comfortable having oral sex with Gretchen while you were dressed as a girl also."

The conversation was so heavy that I thought I needed to re-think my sexuality. I did re-think it. I was turned on by Gretchen suggesting to me that I suck Kevin's cock. I would not seek Kevin out or any other man for that matter, but when Gretchen was sucking him and indicating for me to do likewise, it seemed normal in an abnormal way. It was just part of what was happening. As far as being feminized, I had already come to grips with the euphoric feeling of satisfying someone sexually. I did wonder however, what Ashley meant by magnifying my weaknesses. I was sure to find out.

And I did very soon. Ashley set up a date with a man that she thought might be a good candidate for our planned activity. She knew that he was not gay and seemed pretty certain that he was not a declared bi-sexual. She said that Kevin would have been the ideal candidate, but Gretchen had beat her him. The guy, Clay, was a business associate of Ashley's. She had already fucked him previously and it seemed clear to me that he measured up to Ashley's requirements. As in his cock 'measured up' to her needs. She already confessed to being a size queen. With her stature and looks she could afford to have high standards.

We decided to go with the brunette wig. Clay was coming over for wine and snacks. Ashley had made it clear that I was to be there, but she told him her roommate Ra'Chelle was the one who was going to be there. He didn't quiz her too closely about Ra'Chelle. He knew that she had a roommate, but he did not make any connection before this, so Ray had never met him. I wore the over-the-neck breastforms again. Since we were dining in, Ashley wanted to do what she had suggested with my little cock. I was freshly shaved. When it was time to get ready, Ash laid out my clothes that I was to wear. It included a pink bra with a full necklace to hide the breastforms edge. I wore a little white halter top. The surprise was when she had me put on a pair of shimmering stockings like the pantyhose I had worn with Gretchen. They were held up by a pink garter belt. Over that I wore a very open crotchless pair of lacy white panties. Instead of tucking my little dicklet, Ash placed a golden chain cock ring under my balls and over the top of my dick. There was another chain about two inches long which attached to a ring just under my penis glans. In addition, small golden chains fell from the lengthwise chain. The glans ring had some give to it and it fit tightly to my little dick. The panty opening was so wide that my entire front and backside were fully exposed. That was the idea. It added a very feminine touch of white lace and left the penis jewelry out front to be the star of the show.

My cock was hard and Ashley told me that we would have to take care of that in the future, but that night we were going with the new cock jewelry. When everything else was on, she did my makeup and arranged my wig just right. My eye liner was dark and the eye shadow was a bright blue with pink highlights. She dusted on some pink glitter over the deep blue. My lipstick was hot pink. I thought I looked great. Ashley had purchased a pair of pink 5" stilettos in my size. I put my foot in each one and walked around the room to get accustomed to them.

Ashley did her own makeup in a similar style. She wore a yellow half bra with a matching thong. When she kicked on her high heels, she again towered over me by quite a bit. She led me over to the full-length mirror and we admired my cock jewelry. It did accentuate the fact that I had a dick, however small, but the jewelry seemed to add to the effect of the rest of my ensemble. I also wore dangling gold earrings. Ashley mentioned that if we liked this style, we would get my belly button pierced and add a dangling set of chains there also.

When Clay arrived, Ashley introduced me as Ra'Chelle. He was very gracious and could not keep his eyes off either of us. I was charmed that he paid so much attention to me. He did not mention my little dick or even my cock jewelry. He just said that we both looked fabulous. He was looking good himself. He was about 6'-3" and a solid muscular 220 pounds. We had some wine and snacks and talked small talk. As the wine did its work, the talk turned a little more toward the adult topics. Clay said that it was indeed a treat to be in with two beautiful ladies. As he grew more aggressive, Ashley began kissing him and welcomed his hands on her ass and breasts.

"Clay," she said, "Let's go to the bedroom. I want Ra'Chelle to come with us. Do you mind?"

He had questions, but the thought of turning down Ashley was not a possibility. He quickly agreed. We adjourned to the bedroom where Ash removed her bra and let Clay have his way with her soft swaying breasts. As he buried his face in her cleavage, Ash held her arm out for me to come closer to her. She pulled my face to hers and kissed me deeply, pushing her tongue past my painted lips and into my mouth. She moaned as Clay sucked her nipples.

For some reason this foreplay had an opposite effect on my penis. Call it adrenaline rush or fear of being humiliated, but my little dicklet recessed to an almost flaccid state. Ashley had mentioned that we would need to deal with my unwelcomed erection, but I don't think there was any physical reason for me to shrink back to my 'little boy' size. The chain jewelry was not uncomfortable at all. Rather, I found it excitingly erotic. Just the idea that Ashley thought we should showcase what I had always been ashamed of amazed me.

"Clay," she said, "I want Ra'Chelle to prepare us for sex. Please, Ra'Chelle take my thong off and make love to my pussy."

She lay back and held her legs up allowing me to remove the pretty yellow thong. Her pussy was bare and dripping. I gently moved to my knees between her legs and began to lick her moist pussy. She moved to my rhythm as I licked her slit up and down spreading her juices all over her sex.

Clay had removed his clothing. Ashley asked him to come near the bed and let me prepare his cock for fucking her. He approached the side of the bed and I moved from her pussy over to his throbbing white cock. It was huge. Bigger than Rod's. All I could do is lick the head and all under and around his manhood. I took as much of his cock into my mouth as would fit. I could taste the tangy sweetness of his flowing precum. I sucked his cock for several minutes until Ashley held her hands toward him. He mounted her and his huge cock slipped easily into her well lubricated vagina. The squishing sound of their fucking made the whole encounter seem so erotic and so amazing. He thrust his cock into her time and again. He would pull almost all the way out and then bang himself quickly into her making a popping sound as he contacted her pussy. This went on for several minutes. Ashley came twice. She was making him wait to cum and before he accidently gushed into her, she got up on all fours on the bed.

"Ra'Chelle, lay under my pussy while Clay fucks me. I want you to see this huge cock satisfy my pussy. You can have the last of me with your mouth, but now I want you to watch this big cock wreck my little pussy.

I knew what she wanted. Without regard to my makeup or curly wig, I lay my head under her pussy. Clay got behind her and inserted his massive cock into her. I could see and hear everything. The slosh of their mating sounded like rubber boots being pulled out of the mud. Her moans were getting more and more shrill as she encouraged him.

"That's it, Clay, fuck my pussy. Make me cum on that big cock. Fuck me."

As he pounded her, his big balls were swaying back and forth hitting me in the forehead with every stroke. He was grunting and getting ready to cum.

"That's it, Clay, fuck me. I want you to pull out and feed your cum to Ra'Chelle. Hurry. She loves cum."

I strained my head back more and he sloshed out of her, hitting me in the face with his heavy manhood. He moved forward and found my waiting lips. In that position, I could only take him so deep. He tensed and began jetting blast after blast of cum into my mouth. I could not swallow well in that positions and his cum overflowed and got all over my face and neck. His balls were on my head and I held his cock in place over my nose while he finished shooting spurt after spurt of cum all over me.

When his cum slowed to a drip, Ashley moved him away from herself and dropped her pussy onto my cum filled mouth and face. She basically raped my face with her dripping pussy. She fucked my tongue like she had never been fucked. Then she exploded and let loose a torrent of girl cum all over me. I lay there with Clay's massive cum load in my mouth and all over my upper body and then Ashley had drowned me as her pussy squirted her girl cum all over his guy cum.

After a brief rest, Ashley indicated that Clay could fuck her again and Ra'Chelle would fluff him until he got hard. She directed me to his semi-hard cock and I took the limp member into my mouth. As I sucked him, he began to get harder with each moment. He fucked my mouth until he was ready to mount Ashley again. There was no hesitation from either of us. Having the most beautiful and voluptuous woman alive calling the shots seemed to melt our manhood away into a flowing river of compliance. While I was licking and sucking him, all I thought about was pleasing Ashley.

When he entered her again, she said, "Lick his balls, Ra'Chelle while he fucks me."

I complied. His ball sack was sweaty and had a special musky aroma. I placed my mouth near him and tried to lick and stay with his rhythm. Ashley was enjoying the big white monster and she wrapped her legs around his hips drawing him tighter to her and allowing him to penetrate her to his fullest.

"God, fuck, Ra'Chelle, he is banging my uterus."

I rubbed his ass and placed my manicured fingers around his scrotum while he plowed his big cock into my friend Ashley. God, how I envied his huge cock. And yet, I was still more in tune with following Ashley's wishes. It was almost like Clay and I were equal. Each one was to pleasure Ashley.

He shot his second load of cum deep into her pussy. As he softened and pulled out, I moved up and began sucking and licking her pussy. His cum was slowly flowing out of her and I took it all in. After the flow stopped, Ash indicated that I should clean Clay's cock. It was semi-erect and I gave him a tongue bath licking his cock and balls until he was completely soft.

Ash got on top of me and pressed her naked body to mine. Then she had me stand in front of her while she sucked my little dick until I came in her mouth. She kissed me deeply and pushed my cum load back into my mouth. I swallowed my cum. I was full of Clay's cum and my own and I was completely satisfied.