My Friend Ashley Ch. 03

Having broken up with my girlfriend, Karen, (or rather being ditched because of my little dick) I had moved in with my childhood friend, Ashley. Ash was a college track athlete, tall and gorgeous. Way out of my league. However, one night I drunkenly tried to move on her and she saw my little dicklet. She had sex with me anyway. This was the start of my education of how to please a woman orally.

When I had sex with her friend, Gretchen, I sucked my cum out of her and satisfied her orally also. Since Gretchen was bi-sexual, there was no chance that I could develop a traditional emotional relationship with her. I was beginning to take the pragmatic approach. I was better off living with Ashley and fucking Gretchen occasionally than I would have been otherwise. Gretchen must have liked my oral talents for she let me have sex with her so I could suck my cum and lick her pussy.

One evening Gretchen invited me to her place. I thought, 'great, I am having sex tonight'. When I got there, I learned that another friend was coming also. Mandy showed up half an hour later. It was plain that they had been lovers at some point. Snacks and drinks were arranged and we all settled in for deep conversation. In due time, Gretchen informed Mandy that I was quite the oral lover.

"He eats pussy better than some of my girlfriends."

"Sure," deadpanned Mandy.

"No, really, Mandy. Come on, let's get in bed and I will let you be the judge.

Mandy seemed reluctant, but Gretchen insisted that we all get naked in her bed. Mandy was not nearly as cute as Gretchen, but she was not unattractive either. She was about 5'-5", 120 pounds, B cup size breasts. Gretchen moved over and kissed Mandy in a very sensuous way and began rubbing her breasts and crotch. This was hot to me and my little dicklet was standing at full attention. For a while, it did not matter how hard I was. I was just a voyeur. Mandy moved up to Gretchen's huge breasts and sucked her nipples. Her areolas became distended and her nipples were like pencil erasers. I thought that I might have to masturbate for any relief until Gretchen rolled Mandy over.

"She's ready for your mouth Ray. Show her what she has been missing."

As hot as the scene was, I was still a little put off with being called upon to perform oral sex on an obviously homosexual woman. It was almost humiliating to be used as a sex organ. However, Gretchen seemed in no mood to negotiate and I was actually in bed with two women at the same time. Who was I to complain? Mandy seemed a little harder to convince. I was not sure whether to proceed, so Gretchen moved her lips to Mandy's smooth vaginal lips and began licking and sucking her pussy. She raised up and guided me to her place and began kissing Mandy on the lips while I dipped my mouth to her steaming opening. She did not taste as sweet as Ashley and Gretchen, but she had not been freshly fucked as they had been when I tasted them.

I was certain that I was only there to perform oral sex on Mandy according to Gretchen's buildup. I doubted if Mandy was bi. While I slurped her pussy juices, Gretchen made lover to her mouth and breasts. Whether from dual stimulation or just the fact that Gretchen was kissing her, she came in a violent rush. It was almost as if she fought the orgasm, but in the end, she gave up and started humping my mouth as I locked my lips onto her willing pussy. When she calmed down and I moved off her, Gretchen said, "What do you think now, lover?"

"It was good, but I had trouble getting into it at first. I mean, he is cute, but he is a guy and I can't help thinking of him that way."

Gretchen lowered herself on top of my tiny but raging dick and started fucking me wildly. I came so quickly that it surprised me also. It was like she knew that she could get me to blow my load into her so she could have my mouth that much quicker. She held her hand over her vagina and rolled onto her back. As I approached her pussy with my lips, I could feel Mandy moving back over and sucking Gretchen's boobs and kissing her. I sucked my cum and paid careful attention to her clitoris. It was very firm and I pierced my lips with her engorged nub.

She let loose a muffled scream as Mandy was kissing her lips. As she moved her hips to fuck my lips, I held tight to her girl cock and pushed ever harder. She flailed her legs as she had another orgasm. When the initial rushes subsided, she began moving her hips in little movements as I followed her rhythm with my lips. After she began to relax, Mandy seemed more into her than she had been with me.

Then Mandy said, "Wow, Gretchen, what have you done to this guy. He is your little boy toy, huh? But you were right. He does know how to pleasure a woman. I don't know how you felt about his little 'thing', but his tongue was indeed satisfying. Shame that he has all that other stuff attached to his body. Otherwise, we could be great girlfriends."

Gretchen got a little coy smile on her face like a light bulb had just gone off.

"You know, Honey, you might just be on to something. I mean, not very tall, slim, not very hairy, cute face, nice legs, good ass. What's to say that we might be able to work on a little transition and we would have a cute girlfriend?"

That was out of the blue to me. Going from being sexually celibate to having sex with three women is a short span was giving me a confidence boost. But these ladies were talking about making me into their girlfriend. I turned bright pink when I heard that. Surely they were teasing me. I could not come up with a verbal response. I was waiting for them to burst out laughing. The girls were very serene in the afterglow of their orgasms. I was post orgasmic also and did not want to make a fuss. I decided to let it drop.

But it did not drop. Gretchen asked me, "You know, Ray, with your oral talents and sweet personality, you might really make a pretty bi-sexual girl.

"Well," I answered, "You are a pretty bi-sexual girl and I don't look anything like you."

"Not exactly, I will grant you, but you have a cute little clitty sized 'you know what'. I think you will look pretty sexy if we clean up your pubic hair and the rest of your body hair. Mandy has no desire whatever to be with a man and she enjoyed you pleasuring her. I might have pushed her to do that because I highly touted your oral talents, but she was definitely into it when you went down on her. She would never suck your cock, but packaged a different way, who knows how she would reciprocate good oral sex."

Things turned quickly after that talk. Gretchen invited me over for dinner the next week. I was not expecting our little talk to be much more than talk. After we ate a light dinner, she took me by the hand and led me to the bathroom. She had me undress and stand in front of her. I told her that I felt like a piece of meat standing there.

"See, you are already experiencing what we girls go through."

She applied a film of lotion all over my legs, chest and the area above my little dick. She had me wait about ten minutes, then turned the shower on and had me rub away all my hair. I was completely hairless after this. She handed me a razor and told me to shave my underarms and crotch. This took care of any pubic hair the lotion could not be applied to. She changed the razor blade and had me shave my face very closely. When I dried off, she dusted me with a lilac scented powder. I stool naked with my tiny cock sticking out. I looked like a little pre-pubescent boy. Gretchen stepped back and admired her work.

"Damn, Ray, you already are looking good. Tell you what, for the sake of our adventure, let me call you Ra'chelle for tonight. That is feminine and sexy also."

It couldn't just be like RACHEL or something like that. She spelled it out.

R, A, apostrophe, C, H, E, L, L, E.

It sounded like Rachel but was like RA, SHEL. With an apostrophe to emphasize the front syllable. She was really into this. She must have been planning this since our last sex session. She had me sit in front of her vanity and applied makeup to my face. It took about twenty minutes and the steps she took were amazing. When she was done, I could not believe the image in the mirror. She was quite proud of my look.

She went to her dresser and handed me a satin like sleep set. The panties were cut high in the legs and swept loosely up to the high elastic band. They held nothing and my little cock bobbed under the shimmering material. She next gave me a matching top with spaghetti straps and told me to put it on. When I was set, she had me lie on the bed and she slowly started sucking my hard-little weenie. I came very quickly and she held my cum in her mouth. She moved up and kissed me running her tongue between my lips and moving them apart. That done, she opened her mouth and dropped my entire load of cum into my mouth.

I had eaten my cum already and I was growing accustomed to the taste and texture. It seemed to be so natural following the guidance of this hot buxom woman. I was falling into a trance and was so compliant with her every wish. I was like my free will and former self had vanished. Not taken away, mind you, it just was pushed way back in the recesses of my brain.

After snowballing my load back to me, she touched up my lipstick. We turned on some music and relaxed sitting up in the bed. I was completely hairless except for my head. I had on deep eye shadow, eyeliner, mascara, lipstick and cheek coloring. The sleep set felt so sexy to my skin. My little cock was limp and drawn up to its smallest size. The good thing about removing my pubic hair was that you could actually see my cock now. My scrotum was taunt and barely noticeable. Damn it, she was right. I did look like a pretty girl.

"Hot is hot, Ra'Chelle. This is a good start. I can't wait to get you fully dressed and made up. I want to show Mandy when we are ready, but I really want Ashley to see this. She will be amazed and not have to answer her guy friend's questions about why she is living with a guy."

Over the next month, Gretchen and I spent a lot of time together. Ashley was not too keen on the idea at first because she thought that Gretchen was just fucking with me. Having regular sex is a powerful motivation. Ashley talked to me about what Gretchen was doing with me.

"Ray," she told me, "I know you are captured in the euphoria of sex with Gretchen and me, but are you going along with her because you don't want to rock the boat, or are you really enjoying the feminization?"

"I know, Ashley," I stated. "At first, I was startled by her ideas. It started out as a kind of bet between Gretchen and Mandy. Mandy went along with the idea even though she only dates women. When she gave me a thumbs up for my oral talents, it changed my whole perspective. Never before had I been referred to as a skilled lover. I don't care that it was because I can satisfy a woman orally and not with my little dick. It was a new experience. When she started leading me into the fetish of femdom, I slowly began enjoying being the center of attention. I was surprised that it turned me on so much. Gretchen gives me a 'pity fuck' every so often to keep me interested. She wants to dress me up fully and have me be present while she fucks a stud with a big cock. She says she will take care of everything and all I have to do is look pretty and participate."

"Shit, wow, really?" Ashley asked. "Do you really want to do that?"

"Yeah, I think it will be hot as hell watching her get dogged by a big cock. I know she wants me to suck her off afterward and I am okay with that."

"God, bless, Ray. That is hot. I am shocked. But if you both want to go for it, then do it. That intrigues the hell out of me. I mean, you ate me out after Rod had fucked me that one night. I was so hot with that. It was unbelievably sexy. Also, I think it is hot for a guy to eat cum. It just seems so taboo and so wild. I might have to see if Gretchen will let me include you in one of my escapades also."

The more we talked, the more Ashley believed that I was really into my new feminized role. She began to refer to me as Ra'chelle also. She called Gretchen and told her that she wanted her to give me a complete makeover and for us all to have a girl only sex party. Gretchen was moving that direction already. She had been buying me lingerie, high heels and dresses. We were getting close to the full dress-up date. This would be a dress rehearsal for that. Plus, I might even get to fuck each of them on our 'girls' date. I was for sure that I would be eating their pussies and they both seemed to like the idea of me eating cum from them.

Starting then, Ashley and Gretchen had me get rid of my guy underwear and tee shirts. From then on it was panties and a training bra all the time and sexy panties and lingerie to sleep in.

The day of the 'girl' party, Ashley took me to get a manicure and pedicure. Gretchen had purchased a high quality curly black wig. They dressed me in stockings and high heels with a baby doll nightgown. They wore baby dolls also and heels. Their legs were pretty enough and perfectly tanned that they did not need stockings. Gretchen did my makeup a little 'sluttier' this time. We had wine and snacks until it came time for bedroom activities. I made love to Ashley with my mouth first. Gretchen saw the opportunity and told Ash, "You know that makes you bi, Girlfriend. You just had a hot girl go down on you. I want my turn."

Maybe it was the wine. Maybe Ashley was lowering her defenses. Whatever the reason, Ashley just moaned a little and Gretchen followed me in and began eating Ashley's pussy. Her objections seemed to have melted away and she caressed Gretchen's head as she dove into her pussy. It was hot for me also. I fucked Gretchen while she was pleasuring Ashley with her mouth. After Ashley had cum twice, Gretchen sat on my face and fed me back my ample cum load. It ruined my makeup but no one cared at that point.

It seemed that Ashley and I both were experiencing a transition in our sexual horizons. When we talked about it later, Ashley admitted that she just went with Gretchen's advances and let her have her way. She didn't think there would be any change in her overall sexuality but reminded me what she had said many times before. "Fuck their labels."

Gretchen was more that pleased with the dress rehearsal, as she called it. I was wearing lingerie every day and night per Gretchen's instructions. When Ashley and I were both at home, she seemed to like seeing me in long gowns or baby dolls or whatever I had on. Some of it was Gretchen's nighties, but the panties were for just me. Occasionally Ashley would come into my room and ask me to suck her off. I was not always in makeup but it didn't matter to her.

When my coming out party was near, Gretchen had me order some breastforms. They were of high quality and fitted over the neck. I wore a necklace to hide the top and make it look more natural. I was shocked at the dress and the amount of cleavage she had me showing. She had me put on a pair of bikini panties and tuck my little cock back into my buttocks. She then gave me a tight pair of glossy leggings. I put them on and they also snugged my cock up. When I stood up, I looked like a girl between the legs. My heels were 4" and close toed. The dress was navy and very low cut. I worried about the texture of my chest, but she had applied a base makeup and it made me look very natural. The dress had a mid-thigh hem and I thought my legs looked delicious in the tights.

I was over at her place when her date showed up. It was a guy she knew who was a soccer trainer and coach. He was British. And he was tall and muscular. And he was black. His name was Kevin and he seemed well aware that there were three on the date. I guess Gretchen had prepared him.

We went to some clubs. Kevin danced with both of us and we danced with each other. Gretchen told me several times that if we weren't with Kevin, she could easily spot a few girls she would like to fuck. I told her that I would like to fuck the same ones she pointed out. She teased me, "Just like a horny bitch. Trying to take my pussy away before I have a chance to get to them."

I knew she was kidding so I kissed her on the lips. We came back to our table and continued to touch each other. I wasn't particularly worried about dramatizing a female voice for Kevin. It seemed that this was a totally freelance outing and he did not seem to mind. Gretchen would feel my boobs and reach her hand under my dress. She would kid me about having to keep my little cock under control if I was to be a proper lady. For his part, Kevin seemed to enjoy the lesbian overtures. When we had had enough dancing, Gretchen leaned over and whispered in his ear. I didn't hear it, but he seemed eager to pay the tab and leave.

We got back to Gretchen's and had another drink before settling on her couch. Kevin sat between us and began making out with Gretchen. He was openly caressing her huge breasts until she stood up and took off her top and skirt. She was just in a thong and the beautiful lacy bra that matched. She reached back and unclasped all four of the bra hook and eyelet fasteners. She tossed the bra aside and spread her legs around his body. He feasted on her massive breasts, sucking her nipples while she face fucked him with her melons. It was hot. She leaned over and kissed me while Kevin was mouthing her nipples. Finally, she stood up and took our hands and headed us to the bedroom. Inside, she stared removing Kevin's pants and shirt. His shoes and socks were off next. He stood there in a neon thong with a bulge the size of a small salami.

She had me unbutton my dress and step out in my bra and pantyhose with heels. She had him step closer to her and then rubbed all across his protruding manhood. When she took his waist band in her hands and lowered the thong, a ten-inch-thick cock plopped out. Gretchen smiled at me and said, "Now this is a cock, Honey. This could almost make me forget women. Look at this, Baby. No, feel this meat."

She held his cock and with her eyes made me come forward and take it in my hand also.

"Feel the smooth texture, Ra'Chelle. Have you ever seen one so big and thick? Not to mention the rich coffee color."

His cock was uncut. The foreskin was supple enough to cover the whole head even though it was completely erect. Gretchen held him just below the bulbous head and gently moved the skin back revealing the plum sized purplish pink head. A drop of precum was already formed at his opening. Gretchen leaned forward and placed her lips over the dollop. She sucked it off and had me come over and kiss her. She thrust her tongue past my painted lips and shared the sweet taste of his nectar with me. She motioned for me to het on my knees beside her. As she engulfed his cock head with her mouth, she moaned and squeezed my hand tightly.

"God, Ra'Chelle, this tastes so sweet. Here taste it."

She pointed the ebony lance to my lips. I hesitated and then covered the head with my mouth. The sensations were intoxicating. Not only did she want me to watch her get fucked by this big black cock, now she wanted to share it with me. There was no time for soul searching. She was in control and I was following her every lead. She took as much of his cock into her mouth as she could without gagging and then motioned for me to do the same. I was putty in her hands. I had not the slightest hesitation when she instructed me. She held his cock up and licked his scrotum all over. She moved back and gave me a nod to do the same. His ball sack was shaved and had the texture of soft leather. His testicles were amazingly large. I would say about three times the size of my little marbles.

When we had his cock slathered with our saliva, Gretchen lay back and Kevin mounted her. She spread her legs enough for me to see his massive prick penetrate her up to the hilt. She was moaning and begging him to fuck her.