My Friend Ashley Ch. 08

After my anal cherry was surrendered, I had no remorse other than the soreness the following day. Sheila and I had taken full advantage of our passage and enjoyed each other over and over. I returned to Ashley's the following morning and got some much-needed sleep. I was a total mess. I had not bothered to do my makeup when I got up that morning and I just wore my coat. Sheila had loaned me a bag to carry my clothes. I did not see Ashley until later that evening.

"How did it go last night, Ra'Chelle?"

"Fantastic," I replied.

"Fantastic? Good. That big cock fill you up?"

"More than that. I am so sore this morning. But I don't regret it. It was so intimate, yet so taboo. I don't know which pleasure sensor took over. I feel so different."

I described more of my experience with Sheila. I told Ashley that Sheila had asked if she, Ashley, was okay with me seeing her.

"Really?" Ashley asked. "That was thoughtful. Did you describe our relationship?"

"Oh, yes," I answered. "I told her that you were a twelve on a scale of ten and that you have always been my best friend. You picked me up when I was down. You were concerned about me after I slept with Gretchen. You counseled me as I started changing and helped me with HRT. Most married people I know have not been through as much together."

Ashley assured me that all her support was out of love for me. She was that type of person. I always knew that, but I would never have known about her other side unless I had lived with her. For someone like me, cursed with a little dicklet, to get to make love to a gorgeous woman like Ashley was a dream come true. I could never have imagined that I would have a sexual relationship with such a hot woman. The basic premise of our relationship had no role overtones, no labels. It is just something that developed. Ashley referred to me now as her bi-gender friend. I thought that was so cute and original. I never had a chance to satisfy her even when I identified as male. My little cock was the fuse that lit my desire to be feminized. My oral skills, on the other hand, were appreciated by both men and women alike. Not to mention another special friend, Sheila.

I got thinking of Ashley teasing me about sharing Sheila's big cock. I knew she was just razzing me, but I did want Sheila to meet Ashley. Sheila loved my little cock jewelry and quizzed me more about where we had found such sexy novelties. We were having some people for cocktails the following week and I asked Ash if I could invite Sheila.

"Of course, Sweetie, I would love to meet her."

"Oh, thanks, Ash. She is curious about you too since I told her how beautiful you are. Is Gretchen coming?"

"Yes. And Mandy too. By the way Mandy has changed somewhat also. Letting you fuck her was probably the best thing that could have happened. She is dressing better and even wearing some makeup on occasions. She has pretty fingernails and toenails now and does not give off that man-hating lesbian attitude. Your cock might be little, but it seems to have made somewhat of an impression on her. I don't think that she has turned completely bi yet. That is unless you count penetrating her with your little clitty. Ha."

"Very funny, Ash." I said sarcastically.

When the cocktail party came around, there were several guys there that I had not met. We were all introduced. When Sheila arrived, the room grew quiet. Ashley, Gretchen and even Mandy were aware of my new relationship. They were all dying to see what the fuss was about. Sheila did not disappoint. She might be subtle at her work, but for the party, she was anything but. She wore a cream colored, low cut top with long sleeves and very tight to her braless D cups. Her nipples were poking pebbles in the thin material. Her black skirt was short and tight also. It barely hid the tops of her stockings. She wore a sexy black stiletto. You could tell it was top of the line. I hated to think what her whole outfit cost, but the effect was mesmerizing. I looked for any bulge in her dress. I did not notice even the slightest hint of cock. It was good because other than Ashley, I thought Sheila was the prettiest 'girl' there. And that says a lot because Gretchen with her huge boobs was outstanding, also. Even Mandy looked feminine that evening. A couple of other girls that knew Ash were there also and looking good.

The guys were quite an eclectic group. There were brown, black, Asian, Caucasian. Six in all. The music was trendy and the conversation was varied from sports to business to political. If you didn't relate to one conversation, you could just walk across the room.

As people began to trickle out, Ashley kissed and hugged them. Some had dinner plans, others, just plans. The evening was still young and Ashley asked Sheila if she could stay a while. She agreed. I think they both wanted to get to know each other. Gretchen was never going to leave early. She was too fucking nosey to miss anything. Besides, I think she was pissed that Sheila might take up too much of my time and she didn't want to miss out on my oral skills. She loved for me to go down on her and occasionally she would take over and ride my face like a small pony. When she got that excited, she came heavily on my face and totally messed up my hair and makeup. That being said, I always presented myself to her as a lovely made up girl.

Sheila and I made it back to my bedroom for a little private time. As soon as I shut the door, we kissed hungrily. I reached under her skirt to find a tight gaff panty. It was high quality because it was holding her big cock in placed tucked into her buttocks. I smiled at her seductively and removed the gaff. When it hit the floor around her heels, I felt her hardening cock flop out of its hiding place. She moaned as I felt her member, allowing it to come to full attention in my hands. I reached around and undid her skirt and let it fall to the floor. When she stepped out of the pile of clothing, I was on my knees in an instant. I stroked her smooth cock while she started leaking precum from the end. I licked the precum off the tip and proceeded to move my mouth down on the head. As was my special talent, I began taking her into my throat inch by inch. When she was all the way down my throat, I felt her legs tremble. I did not want her to cum, so I pulled her out and helped her lie on my bed. In this more relaxed position, she was able to loosen up and enjoy my repeated thrusts down on her cock. As I had done previously, I waited for her to get ready, then took her deeply and waited for the blasts of cum to hit me way down in my throat. She was trying to be quiet, but some sounds escaped from her mouth as she was overcome by her orgasm.

As she softened and began slipping out, I finished ingesting our combined juices. I licked and sucked all the saliva and cum cocktail.

"We better get back to the party." She moaned.

"Yeah, here let me help you with your skirt."

I fastened it back and smoothed it around her hips. She reached for her panties, but I withheld them. I sniffed the crotch and licked my tongue at her.

"I will just keep these as a trophy," I said.

"Fine by me." She replied. "If you want me going back out with a bulge in my skirt."

"I do. And I want it to show. There are only a few people left."

I rose and kissed her, making sure to run my tongue into her lips so she could taste her cum from my mouth. We went back outside. Ashley and Gretchen gave us a knowing glance.

"Ashley, Gretchen," she said, "It is so nice to meet you both. I would love to return the favor and have you over to my place soon."

I walked her to her car and even felt her cock up a few times on the way. When she got in, I gave her another lingering kiss and wished her a good evening.

When I got back up to Ashley's apartment, they were all in a twit about what had happened in my bedroom. I told them to use their imagination. Gretchen expressed that she had some concerns about Sheila pursuing me.

"God, Gretchen," I said, "You will fuck almost anyone if they look good. Male or Female. So why are you so concerned about Sheila? Did she strike you as an axe murderer?"

"No, she seemed very nice." Ashley chimed in. "And you are right, Ra'Chelle. Gretchen, why are you so put up about her? I think you want some of that cock for yourself."

"Well, if it is a big and sweet as Ra'Chelle said, it wouldn't be a bad plan. It is like having the best of both worlds."

"Yes, I know." I chirped.

"She might not really like us being around her and Ra'chelle together." Ashley said.

"No, Ash, I don't think that is it at all. She did promise to invite both of you over, didn't she? Plus, she was concerned about our relationship before she made a move on me. You will just die when you see her house. It was her grandparents. She inherited it. It is old and massive, but very modern inside for the most part. There are some bedrooms that are still a little quaint, but even the bathrooms for those have been remodeled."

We continued to discuss Sheila's charms and I wondered what would happen when she did invite all of us over.

Sheila did invite us over the following weekend. She gave Ashley and Gretchen the tour of her fabulous inherited home. We had wine and cheese and generally just got to know each other. It was just a meet and greet without any sexual overtones. Sheila already knew the basics about Gretchen and Ashley. The rest of the time was just like you would expect from four young women in a fancy house. However, the girls did indeed warm up to Sheila and thought she was a gracious hostess.

During the weeks that followed, we got together a few times for drinks and dinner. As everyone got more comfortable around Sheila, it seemed like the guards came down and she was treated like one of the girls. Gretchen was particularly interested about Sheila's sexuality and probed me constantly for any juicy details that I might like to share. I would smile and tell her that she was just like us. That left the door wide open for interpretation and I loved to see Gretchen stew over how much to press me.

Sheila and I knew that the girls were interested in a little more adult activity. We talked about it when we were together alone. We did not always have sex, preferring to develop our emotional relationship.

Ashley and I were hanging out one evening when Gretchen came by with a client of Ashley's. Gretchen had stayed close and was up to her usual tricks of trying to fuck Ashley's guy friends. This time however, her date was a six-foot-tall volleyball player named Lisa. Her legs went on forever. Lisa was wearing a short mini skirt and a tank style top. Her protruding puffy areolas could be seen plainly through the top. They stayed just a while, I guess so Ash could be jealous of her going out with Lisa. They were going clubbing and I am sure before the night was over, Gretchen would have her face buried between the tall blonde's legs.

Just after they left, Sheila called and invited us over for drinks and snacks. We readily agreed and both of us got dressed in our sexiest clothes. I wore a flared skirt with stockings, garters and platform stilettos. Ashley wore sexy heels and a thong. Over that she wore a short skirt and a thin buttoned top. No bra, of course for Ash. I wore a bustier to hold the stockings. I selected a little cock ring piece. It had a thin black elastic band that snugged around my scrotum. An elegant gold chain went around my little dicklet and connected to a birthstone jewel just under my clitty. Another black stretch band connected between my little balls and attached on the underside to the larger ring. Hanging from the bottom connection, it had a string of four black pearls. I wore no panties. The lower section of the bustier flared below my waist. The stocking garters were wide band black lace ribbon. The bustier was red with black trim and stitching. Ashley thought I looked adorable. On top, I wore a red, low-cut blouse which accentuated my cleavage.

"I guess when we get there, you are going to drop the little skirt, huh, Bitch?" Ashley teased.

"Absolutely, Gorgeous. I am in direct competition with you tonight."

Of course, I knew that I would never challenge Ashley in that way, but I felt spunky and wanted to tease her. I did not know what was about to happen. I knew Sheila was very impressed with Ashley. In addition, Ashley had teased me about sharing Sheila's cock. Who knew how serious she would be about that? None of us were interested in a monogamous relationship and Ashley had shared lovers with me already. In a way, I thought it would be lovely to see Sheila's big cock stretching Ashley's beautiful pussy.

When we arrived, there was not much left to ponder what kind of evening it would be. Sheila had taken a page from my book. She was wearing a sexy demi bra that showed her breasts in a beautiful way. She had on a flimsy see through top that hid nothing. Apparently, she was spray tanned for the evening. Around her flowing hips was attached a dovetail open front skirt. She didn't need stockings. The skirt had a multi-colored peacock look. Her strappy heels were a bright green. In the front was her thick semi-erect cock adorned with my style of cock jewelry.

Sheila's cock adornment had a gold elastic band under the scrotum attached to a gold glans ring. Tiny chains joined the two rings. The drape of the chains under her big cock along with the shimmering top chains made a shiny lining to her wonderful appendage. Ashley was flabbergasted that Sheila just loved our little fashion fetish.

"Oh, my, Sheila," Ash said, "That is a real improvement on our theme for my lovely friend, Ra'Chelle. And an improvement of lengthy proportions. It is just lovely."

We did have wine and snacks, but the theme was already set for the evening. I could see that Sheila and Ashley were bound for each other. Ashley just loves big cocks. I was going to be happy with whatever happened. Here were two gorgeous creatures and I had had sex with both. I longed to feel Sheila's cock in my mouth and up my boy pussy, but the thought of watching her big cock stretch my friend's pussy was also exciting. Ashley was keen on eyeing Sheila's big thick cock since it was absolutely on display. In anticipation of an erotic encounter, her cock was extending the gold chains and stretching both gold bands. I saw Ash getting more and more excited, so I decided to get the suspense over with.

"Why don't we take the party to the bedroom, Girls?"

Sheila led the way while Ashley shed her top and tiny skirt. She was in just heels and a thong when we arrived at Sheila's bedroom. I looked around to see the best way for us to experience the most comfortable positions. First, I kneeled in front of Sheila and gently removed her beautiful gold cock jewelry. I kissed the pulsating head of her cock and sucked her glistening precum from the opening. Sheila moved toward Ashely and embraced her pulling her hips to her throbbing girl meat. Ashley melted her hips into Sheila and ground her pretty thong into her. I moved behind Ashley and pushed my little clitty into the back of her thong while I reached around her and held her soft breasts. I licked her behind the ear. I knew Ashley was turned on by this.

Sheila moved back and Ashley slid her head between her legs and down on her cock. As Ash ministered to the big cock, I took the waist of her thong and pulled it down. She was still sucking Sheila and accommodating the removal of the thong. I took Sheila by her hand and guided her to a straight back cushioned chair. I then took her large throw pillow and propped her back outward and spread her legs. I positioned Ashley over her cock in a reverse cowboy orientation and got two end tables on either side of the chair for her to rest her legs on. Slowly I eased Ashley down and back until her ass was sitting on Sheila's lower abdomen. This allowed me access to the cock and the pussy before the coupling would take place.

While slowly stroking first one and the other's sexy legs, I took Sheila into my mouth. I moved up and down with each stroke being deeper than the previous one. I took most of her cock into my throat but my head contacted Ashley's pussy. I then pulled her cock out and held it down while I made love to Ashley's warm vagina. They we both so wet. My saliva mixed with their flowing juices was creating quite an overflow of love tonic. I alternated sucking one and the other until I knew they were both ready to consummate this first meeting.

Gently I grasped Sheila's cock and moved it downward aligning it with my friend Ashley's dripping pussy. I moved the bulbous cock head up and down her slit until they moved into perfect alignment. When ready, Sheila thrust her cock slowly upward entering the waiting cunt. She slid easily into Ashley while the sloshing sounds of the entry filled the room. They both moaned in mutual satisfaction. As Sheila moved in and out of her pussy, I moved down and began licking and sucking Sheila's balls. I licked the underside of her scrotum as far down as I could go without disturbing their mating.

They fucked this way for a long time. I was amazed at Sheila's staying power. I let them move to each other for a while and then I would suck them both for a while. The love emissions were flowing and I was treated to a tasty potion each time I returned to my oral ministrations. Ashley would have an orgasm and clench up for a second. Then she would thrust her hips even harder to take more of Sheila's cock. Inevitably, Sheila got ready to cum and she started a low shrieking moan signify her impending ejaculation. It was definitely a girl pitched shrill sounding emission. Ash ground her cunt harder and Sheila shrieked as she began bathing Ashley's womb with her warm seed. A froth began forming at the entrance of Ashley's pussy as they pounded the cocktail into foam. Once Sheila had emptied her balls into Ashley, they both came to a satisfied pause. Sheila began softening a little and started moving slowly out of Ashley.

I took hold of her cock and bathed the shiny secretions off her. I licked the cum and foam from her cock, then turned my attention to Ashley's dripping pussy. Their juices were the most unique taste I had ever experienced. The cum was sweet with a little metallic edge and a musky overtone. I had tasted both in one on one sex and they both were wonderful. This was a whole new thrill. The blended taste contained cum, precum, my saliva and their mating sweat. It went straight to my brain and I wanted more. I bathed my whole face in Ashley's wrecked pussy and made a terrible mess of my makeup. While they rested, I went to Sheila's vanity and re-applied all of it again.

When I came back out, Ashley was sucking Sheila's cock again getting ready for round two. I moved back to the bed and took over sucking Sheila. Ashley giggled and let me deep throat her. We took turns sucking her back to hardness.

This continued for hours. Sheila fucked us both in the ass. I was wondering where she got her stamina from. When she took Ashely's back entrance, I was positioned under her pussy so I could lick her to orgasm. Ashley was moaning as Sheila sunk her hard cock deep into her bowels. While Sheila was fucking my back door, Ashley was licking my little limp clitty. Sometimes I missed my lost male orgasms, but the total feeling was amazing. Pleasing two wonderful companions was my orgasm. We were all so pretty and yet wanton.

We continued this relationship and eventually Sheila asked us to move in with her. Ashley had no problems giving up her condo and I was a guest anyway. My job was going quite well. Ashley's business was booming and she had plenty of competent employees. She just had to make sure they were taken care of, so no one wanted to bolt and start their own business. Some would inevitably try because Ashley was a great role model. Sheila eventually left her technical job. She was needed full time to administer her grandparents' charitable foundation. This kept her plenty busy watching out for bankers, lawyers and others who would try to steal the money. Sheila had plenty of money in her trust fund, so she didn't have any reason to misappropriate the foundation. Her love of her grandparents, especially her grandmother was the motivation that kept her in charge.