Me & Shari Pt. 04 - Diamond in the Rough

The troops had been gathered and the help was on the way. After Jan's breakdown at the pool party, Shari, ever the helper, thought that she had an idea of what had thrown Jan into a tailspin. She and her counselor friend, Dan were meeting Billie and Jan's house. Billie had stepped in with Shari when Jan had her break and had been a part of the group and Jan's friend for some years. Come to think of it, Jim and Jan were the ones who asked Billie and her husband Chuck to join our group when we had decided to bring in more people.

I picked up Kurt and was taking Jim golfing while to professionals talked with Jan and help her figure out not only what caused her crisis but what her crisis was. Jim was not sure that he wanted to leave her this way and it took some convincing that she was safe, and we were only minutes away if they needed him. It was finally Dan that convinced him that he was licensed counselor, and she was going to be well cared for.

We had to wait for our tee time, and I knew that Jim was distracted, and he kept checking his phone. Normally he kicks Kurt and I's butts on the course but not today. I kidded with Kurt that we should have been playing twenty dollars a hole and that was before the fourth hole. I told Jim that I had promised Shari that they would have a few hours and it would be her texting me with news. He agreed and visibility relaxed, a little, and started playing better.

By the ninth hole he was back to his normal game. We played the rest of the course at our normal pace and finished in just over two hours. While in the bar enjoying a cool down beer, I texted Shari. She said that they were going to need more time and to try to keep Jim distracted, and that he had texted Jan a couple of times and they needed her focused on them right now.

I told Kurt that we still on duty and Jim needed to be more distracted, then I had an idea. I declared it as one of our rarely used guy's only days and said that we were going back to my house and have fun. Kurt loved the idea, Jim said okay but he knew why. I drove us all to my house and got us settled in with beers. I said that we had not had a day for just us in probably three years. I turned on some porn and told them that I was still horny from last night, even with the after party and the morning wake up.

Kurt said he and Becky fucked like rabbits after we left but Becky made him stop because she was supposed to go shopping with her sister in the morning and she wanted to be able to walk. Jim broke down a little and said that he had barely slept, and Jan would not let him touch her through her sobbing. Kurt and I moved to each side of him and hugged him. Kurt told him that guys can be compassionate just like girls and opened his shirt placing kisses on his chest. I helped him out of his shirt and started undoing his pants. Kurt stripped off his cloths while I pulled Jim's pant off. I stepped back to strip and Kurt resumed kissing his way down Jim's belly to his cock. Once naked, Jim beckoned me to stand on the couch so he could suck me.

Kurt tried his best to take all of Jim's huge dick when it reached its full glory. Jim was easily able to take all my modest in comparison sized cock. Kurt tapped my leg to switch as his mouth was getting sore. I knelt on the floor in front of Jim and Kurt stood on the couch, presenting his member to Jim. I concentrated on Jim's cockhead tickling the sensitive underside with my tongue until it started twitching then lowering my mouth down it as far as I could. Kurt was fucking Jim's mouth at a steady pace. We fucked this way for a while till I thought that Jim was getting close. I stood and found a bottle of lube in the side table and slathered up my ass.

I was not sure that I could take all of him, but he was going to get to fuck something today. As I climbed on Jim's lap Kurt started to move but I told him to stay. He let Jim work his cock with his mouth as I aimed Jim's massive cock at my ass. I slowly lowered myself onto that huge dick and let it fill my ass. Jim moaned out as I sank down onto him. Somewhere in the back of my mind I heard my cellphone go off, but it was going to wait now. I took Jim's hands and put them on Kurt's ass pulling his cheeks apart giving me access to his puckering asshole. Jim pulled Kurt's cock deep into his mouth, my tongue found his warm hole and probed in as far as I could reach.

Kurt unloaded in Jim's throat, Jim unloaded in my ass, not deep but I sure felt its warmth inside me. Kurt pulled out letting the last of his cum dribble onto Jim's chest. Jim's hands dropped from Kurt's ass to my waist while he continued to pump cum in my ass. Kurt lowered his head between us and took my cock into his warm mouth. It took my right over the edge, and I quickly unloaded into it. After I climaxed, I realized that I had dropped all the way down onto Kurt's dick and my ass was being stretched to its max.

We untangled from each other, Jim thanked us and said that he really needed that. When I was able, I retrieved my phone and read the message. I asked Kurt if Becky was home yet, and he said probably but if not, she could be soon. I told them that Shari said that they were ready for Jim to come home, and they wanted Kurt and Becky there too. I told her we would be there soon.

Related to me later but I will insert here. After we had left with for the golf course, Shari, Billie, and Dan went out to the patio where Jan was curled on the lounger. Shari sat at her feet, Billie beside her, and Dan pulled up a chair next to them. Billie touched her arm and said her name. Jan rousted and realized that she had company she started to try to get up, stammered Hi and tried to turn to host mode. Shari stopped her and told her to relax, they were all there to talk with her. Jan sat back and looked at them, realizing that one was a guest she did not know and tensed up again.

Shari reached out and took her hands in hers and said, hi, I am Shari -- I mean Steven. I am here to help you through a crisis. I am your friend and I care about you. This, indicating Dan, is my friend and my counselor, I asked him to come because I think he can help you. Dan held out his hand and Jan took it. He said, hi, my name is Dan -- Daniella at birth. I am a licensed counselor at the youth center. I specialize in transgenders in crisis but can help with all kinds of mental health issues as well. I am here because my friend asked me to help with someone she cares about. Billie laid her head on Jan's shoulder and Jan reached up to caress her cheek. Hi, I am Billie -- I mean Willamina, DO NOT EVER REPEAT THAT! I am just a slut for huge cock, and I am here because I love you and I feel partly responsible for what happened last night. I misread what was going on and made it worse.

Jan looked at them all and started sobbing again. When she quieted, Dan asked for them to fill him in on what had happened the night before. Shari and Billie related the story and Jan was able to fill in just a few blanks. Dan listened and when they finished, nodded, and asked Jan why she thought she needed to be taken like that and what it was going to accomplish. Jan took a deep breath and steadied herself. She told them that she had hoped that it would make her want to be a woman again. Once she told us what the problem was, they could start talking about it. Dan asked all the right leading questions and took her back to when she first started feeling like she was not a woman.

She went clear back to middle school and slumber parties once she reached puberty and the girls all spent part of the night comparing their bodies. How as the other girls started sprouting breast, she sprouted a clit and mosquito bite breast. She spent a lot of time pulling and tugging at her chest hoping that it would help her boobs grow but the only thing growing was I huge clit and her legs. By freshman year of high school, she was over six foot tall and found out that she was also good at basketball. The boys were all afraid of her and teased her about her flat chest and the weather up there. She focused all her energy on basketball being the mean girl to the boys and defending the few girlfriends she kept since grade school who thought it was cool hanging with a star athlete. High school was torture, but she did finally bloom in college. Six foot five and an all-state basketball title got her into a division one school on a full ride.

The girls on the team became her new best friends and she found a couple that became lovers. Her breasts did finally grow into an almost A cup with perky dark nipples. They looked nice on her tall thin frame but not to her. Her girlfriends enjoyed the huge clit and when they found that they could ride it like a penis and not worry that they might get pregnant. Jan herself found that she could also reach climax that way and rarely needed penetration and liked being the boy fucking the girl. She also liked sucking on titties and eating pussy.

Her senior year with the WNBA stiffing around, she met a tall hunk of a Lacrosse player that started pursuing her days after they first met. She had stifled any interest in boys since grade school and repeatedly blew him off. He persisted until he finally wore her down enough to agree to go on a date.

He did everything right if he was dealing with a normal woman. Jan was pleased that he tried so hard to charm her with his chivalry. She did enjoy his company and they found a teasing banter that made it comfortable to do nothing but sit and talk. They talked about where they saw themselves after school, how long it was going to take to become millionaires, what island they would buy when they did. When she did finally sleep with Jim, it was amazing. He loved her boy body, and he could never give her breast bumps enough attention and he found out that her nipples could be extremely sensitive. He learned how to eat her pussy and when to switch to her clit for maximum effect. She learned that his big cock could fill her like she had longed for and loved feeling him cum in her.

Soon Jan was spending less time with her girlfriends and all her free time with Jim. Problem was one of her 'friends' was not happy about it. The NCAA tournaments were over, they went out in the round of eight with a one-point double overtime loss. She was talking with agents with eyes at continuing a basketball career and Jim was staying in the picture as well. Her spurned girlfriend dropped some pictures of her on the internet, and being before it was okay to be gay, the WNBA with all the rumors around it, backed away. Jim and the school stood by her, but the damage was done. She made an official announcement that she had decided to retire from basketball and opt to get married and start a family instead.

They married, had a couple kids who were successful and out on their own, but as the years passed, she found the desire to be a boy floating to mind increasingly often. She had never confided in Jim that she felt like this and instead pushed to have sex with more partners. The group had quieted the feelings for a long time. She had the opportunity to be with other women and use her cock like it wanted to be. When they missed like three parties because of traveling and family stuff, the desire to be a male came roaring back with a vengeance. She was obsessed with becoming a boy and fucking every pussy in site to the point she was losing sleep and when she did sleep, she dreamed about it. Somehow, she got the idea that she could fuck the idea out of her head and knew their pool party was the perfect chance. She found some ecstasy that had taken from a student that had not turned in yet. She waited to take it until everyone was finishing eating and waited.

She turned to Billie. What you did was exactly what I needed and did roll me over the edge. As I was climaxing so many times, I realized that what I really wanted was for my clit to be sucked like a guy's dick and I wanted to fuck you like Chuck does with a big cock. I was ashamed of myself, my body, my life living a lie. I worried what Jim, and the kids would think. I realized I was lost and shut down. Jan tried to shrink back into a ball of sobbing again, but Billie and Shari would not let her.

The group waited till she was able to get her composure back. Billie and Shari stroked het gently and looked expectantly at Dan. Dan reached and took her hand patting it. He smiled at her, telling her that if they were in 'real' counseling, he would respect distance, but this was a crisis case, and not in a clinical setting, the rules were different. His first question was, does your husband love you? Jan said that I know he does with all his heart and soul. Second question, do you love him? She repeated the same answer. Third question, does your family love you? She answered yes, they do without hesitating.

Dan told her that she had those three things on her side no matter what else happened. Jan took a deep breath and asked now what? Dan told her that it was entirely up to her. She needed to figure out her sexuality. There are so many variants now days and it's your job to figure out yours. Do you want to start transitioning to becoming male? Jan thought for a long time and replied, no. I want to feel more male but not be a male. Dan said makes sense, I can see that. Do you feel that looking more male in appearance would satisfy you? Again, more soul searching, no. There are times when I also like dressing to the nines and paint the town red.

Dan asked Jan if she had ever heard of the term pansexual? Jan said yes, that perfectly describes what I feel. She looked like I five-ton weight fell from her shoulders. She jumped up and gave Dan a huge hug, you just saved my life she told him. He accepted the hug but not the credit. No, he said, these two ladies here had a lot more to do with it than me, all I did was listen. Jan asked, what now?

Dan told her first, she should go take a shower and as she washed head to toe, she should imagine that the previous version of Jan was being washed down the drain. Next, she should study herself in the mirror and discover the look that she wants, not the look that conforms to the old Jan. Finally, she must tell her husband. Jan listened intently and agreed with what he was saying. Then Dan had one more order and it was not a request. Shari is going to bring you to a meeting. There will be people there that will know you, but you must listen to their stories and tell them yours. It is important to your mental stability that you have help navigating your journey, where you are now will not be where you end up, Right Shari? Shari told her that her theme songs were Bridge Over Troubled Waters and Long and Winding Road, but she always ended in Shangri-la.

The new Jan stood and straightened up to her full six foot five, towering over the three of us. Dan said teasingly that he was glad we did this sitting down, he would have feared her standing up. Jan gave him another hug that he welcomed. She turned to Shari and told her, you have known me for less than twenty-four hours and you are one of the dearest friends I could ever have, I do not care what happens with you and what's-his-name, but you are always welcome in my home. She lastly turned to Billie, thank you for being the loving friend you are. You did nothing wrong so there is nothing to be forgiven. She drew tiny Billie into her and hugged her head tight to her tummy, I love you to Willamina! Billie screamed; I hate that name! Jan said I know but I had to say it just once and I will never say it again.

Jan disappeared into the house and headed to shower away the old Jan. The rest of us went in to wait. I was a long shower. Jan eventually called Billie into the room. A few minutes later she came out with orders. I have never met the person that is in the other room she said, Dan, she would like for you to stay if you can in case there are questions that she is not able to answer that you might be able to. Shari, she would like for you to get the guys headed back this way but not too fast, she is going to need a little more time to become the new Jan. Oh and have them pick up Chuck on the way. Then she started rummaging through the kitchen drawers mumbling to herself. How the hell did she remember that I used to be a hairdresser in another life. She is going to have to sit on the floor for me to do it giving the scissors a quick snip, snip before disappearing back into the bathroom.

Dan told Shari that he could stay for a while; he was curious where this was going to go. He did not always get to see this part of his work, had to hear about it second hand. I thanked him for coming and helping. She had an idea that Jan had a big issue but knew that it was bigger than her limited skills could manage. Dan told her that whatever it was that she had going on was sure working because she was glowing. Shari told him that he would get to meet what she had going on in little bit.

Billie emerged from the bathroom and told us that she would like to introduce us to Jan, formally Janice. Jan walked out and looked renewed and radiant and handsome all at the same time. Her shoulder length blond hair that was usually pulled back in tight athletes' ponytail was cut short on the sides, longer and a little spikier on top. She wore a pair of off-white linen pants with white boy shorts showing through and a matching linen pull over shirt with no bra. The hair was perfect for her fresh look and would serve her well with her coaching job. More like a guy's haircut that would always be wash and go. It was almost like she had planned this look out a long time ago and was just waiting for the chance to make it work.

They complimented Billie on her barbering skills. Jan said that she felt like a new person and loved it. Her new look embraced both feminine and masculine looks at the same time, and they both worked.

We got to the house, and all headed in the front door, Jim with his long legs in the lead. Shari met him and stopped him and told that that Jan was waiting on the patio and taking his arm, told him that he needed to listen to her first, his questions could come after she said what she needed to say, and it all was going to be fine. We all entered the house, Shari introduced Dan to everyone he had not met yet. We all thanked him for being there for Jan and we all had questions. They told us that it was Jan's story to tell, and Jim was going to hear it first, then she wanted to tell us. We were all there at her request. I told Shari that I liked Jan's new haircut, it really suited her. Shari just said, more than you know. Dan found his way over to us and Shari introduced us again. He kidded Shari that he could see why she was glowing, but she still needed to come to group sometimes. He said that Gloria and Suzi could get out of hand and scare the newbies. Shari laughed and asked him if he thought that anyone could ever control those two, but she did promise to bring Jan if she needed her to, then looking at me said there goes your Tuesday night sex fest. Damn I said.

Jim and Jan spent over an hour talking on the patio. The other girls raided the kitchen and found lots of leftovers from last night to feed all of us. We all watched while trying not to watch as couple on the patio hugged, talked, and cried together. There was a collective sigh of relief when they stood, embraced, and passionately kissed for a long, long time. Billie opened the patio door and told them the show was last night and to get inside so we could eat more of their food. Arm and arm, they strolled into the house. Jim looked different too.

Jan stepped in front of Jim, and he wrapped his arms around her waist. She started hesitantly saying that last night, most of us had witnessed her have a mental breakdown, and that with the help of an incredibly special, loving group of friends, she had come to terms with a very long-time crisis of identity and was now on the road to discovering who she really was. Jim kissed her in the cheek, and she turned her head to him for a real kiss. With the help of Billie and Shari and especially Dan, we think that I am pansexual and have been all my life since puberty. It explains a great deal of things that I have gone through for years. You all know that I love having sex with all of you, sorry Dan, but saying that I was bi-sexual never really felt right to me. There are times I want to be a man and there are also times I want to be woman. There is a path for me to figure this out and I have friends to help me on the way. Jim and I have talked and, with the sex life we have been living for years, we know that things between us will not noticeably change. We told you first because you are all here now and some of you are our oldest and dearest friends. We will be talking with the kids in the next couple of days and the group will be told next month.