A Learning Experience Ch. 05

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Joscelyn2tg
Joscelyn2tg
226 Followers

"Now Honey," I began, "I just couldn't change yet, I'll do it right now... ok?"

Her grin gave her away, so I just handed her the pies and wine, as I ran as fast as I could to her upstairs bathroom to make the change from Jack to Joscelyn. Somehow I knew that eventually I would start really feeling like a transgender Clark Kent! I stripped my male persona away in seconds, washing my face with my cleanser, then lining up all of my make-up "kit" and finishing that as quickly as I ever remembered after shaving every hair visible. My white panties, stockings and bustier were already on which left only the pretty 4" white sandals with straps to put on. Finally I pulled my white silk robe out of my 'fem' clothing bag, wrapping it around me and cinching its belt. A quick look in the mirror and a couples fixes to my hair, and I then piled everything back into my 'male' clothing bag, and headed for the kitchen and some wonderful smells.

"Mmm! That smells great baby!" I cheered as got to the kitchen door.

I dropped my bags by the door and went in, to be immediately clothes-lined by Mel as she brought our mouths together into one of her beautifully sensuous kisses. She had on an average looking and natty robe, and as soon as the kiss let up, the robe was slipped off, showing an almost exact duplicate for my lingerie, except for the color, Mel's was a black silk set, while mine was white silk.

Finally Mel remembered she was hungry too, as we both sat down to a couple hot pizzas. I rummaged around their kitchen until she finally pointed to the drawer with the wine bottle opener. Once I got its cork out, I tested its bouquet and was very happy with my 'selection' from our wine cellar! I filled our glasses and continued chowing down on our pizzas, but I began to see quick flashes of Mel's eyes. One time over to my chest, then back to my backsides. Very soon now, the main event would begin!

As I became more and more excited, the gaff I'd been using was having a harder and harder time keeping my cock undercover. As I finished my pizza and took the dishes over to the sink, Mel came up from behind and began manipulating my very developmentally early tits. Her hands came inside my silk robe, finally realizing their goal of tweaking my hardening nipples, and tenting the bottom of my robe with my ever hardening cock.

"My God I love how your cock flares like that!" She giggled.

"Nasty girl!" I replied, "Enjoy it while I still have it baby, in 16 months, we'll be twins."

"Mmmm," Mel said, "Don't mind if I do..."

Dropping a dish towel onto the kitchen floor, Mel kneeled on it as she then turned me around to face her. She quickly had my robe open, then went to work on pushing aside my panty/gaff and making sure my entire manhood, or in this case womanhood was exposed for her pleasure. She made sure to get my complete eye contact before sucking my entire 7 inches right into her magnificent mouth. No matter how many times I had seen her do these exact same operations, each time was every bit as erotic!

And as she began sucking my cock in and out, my mind went skipping along the fabric of time, and for what probably took 5-8 minutes, became seemingly hours of oral pleasure. The pressure was building as it always did, and I knew I was as helpless as a newborn, my orgasm could not, would not, and most of all dared not disappoint as my mind reeled and crashed into its own unstoppable oblivion.

"Oh Babe! I'm gonna cum!" I screamed in warning, which only made her all the more greedy to get every drop of my cum in her lovely mouth. Three strong shots, a fourth and then a smaller fifth were rocketing down her throat. As my breathing started to return to normal, Mel rose from her knees and grabbed the back of my neck with both hands. I knew what she wanted and accepted her 'snowball' willingly, repackaged it and passed it back to her mouth as it got smaller with each pass. After she swallowed the last vestige of my cum, she wrapped her arms around my neck, and we began to slow dance in the kitchen together. I could not remember feeling more in love with my beautiful Melissa than at that moment.

"Come snuggle with me for awhile baby," she cooed, "I've missed you SO much!"

So we went into the Den and sat down on their giant couch. I saw a blanket on the other end and snagged it over, all the while covering us both within it. Mel clicked on the remote control for the TV, bringing up an old movie from the 1940s. I tucked my head down between her shoulders and breasts, allowing me to take the most refreshing nap.

As I began to awaken, I could smell Melissa's perfume, it seemed so strong now, even though neither one of us had moved. Mel noticed my arousal immediately and quickly straddled me, all while continuing to watch her movie! From this position she could use her kneeling legs to help guide my cock through its paces. Once I had her positioned on my lap with my cock well embedded in her pussy, I used my own thrusts, as well as hers to bring as much force to bear as possible on the sides and top of her pussy. For quite awhile the fucking went along with little interruption, but I could see gradually increasing levels of pussy juice being generated as the thrusts were becoming harder and harder. Now I could hear Mel's vocalization quickly changing to the familiar 'e's that I knew so well, and as I saw her tense-up, I immediately grabbed her arms at the elbows and wrapped them around her midriff as hard as I could, trapping her and pulling her down hard onto my cock as we both orgasmed into a seeming eternity.

Mel got up and made us some popcorn, but I was only able to eat a few kernels before we had both nodded off to a static picture tube. Eventually I got enough energy going to carefully pick Mel up and carry her up to her bed. Once she was settled, I spooned up against her and fell into a complete and dreamless sleep.

"Good morning sweetheart," Mel was saying, "looks like a beautiful Sunday morning!"

I yawned and stretched as hard as I could ever remember, "Mmm! Hello to you too!"

We kissed heavily and our tongues battled to reach the dominance we each thought we wanted from each other. Once I was really feeling awake, I got up and cleansed my face as well as re-applied my make-up. Apparently Mel had already finished that, and was downstairs getting us a little breakfast.

As I got downstairs, I saw the TV on and took a seat on the couch waiting for Mel to finish whatever she was making for breakfast. Eventually she brought out two plates, piled high with bacon and eggs, and then slipped back into the kitchen's swinging doors to retrieve a pitcher of Orange Juice and two glasses.

After we finished breakfast, we cuddled for several minutes, gradually getting each other more and more turned on. But just as I was going to make a move, we both heard the tell-tale 'whump' of car doors closing out in the driveway.

Keys were rattling in the front door's lock, and quickly coming into her own house we saw Cindy, followed immediately by Andy!

"Well! What do we have here?" Cindy sarcastically began, "Could it be 'the' Jack everyone's looking for? No? Josie then perhaps? Did ya disconnect our phone so you could fuck my sister to your heart's content...? Well?"

I didn't know exactly what she was on about, but I knew better than to interrupt her when she was this angry! But then as it turned out, I didn't need to.

"Cindy... I disconnected the phone." Mel said, "Josie didn't know anything about it, now what's the matter, why are you so upset?"

Cindy was now pacing the Den's floor in front of us. I looked over at Andy and he had a hang-dog expression that hid something pretty awful that he would have to say.

"Ok my pet, your turn!" Cindy called out to Andy.

"Josie... I-I'm so sorry for getting you involved with Roy!" Andy said keeping watery eyes on the floor in front of the still pacing Cindy.

"Andy it's..." I tried to reply before once again being interrupted.

"Go on... the rest of it!" She was almost screaming at him now.

"I thought that... if... well, if somehow you two got along, that there might be h-hope for... for us, for... you and I" Andy finished in almost a whisper.

And so, Cindy's warning about Andy finally fell through with the true devastation it could employ, he had sold my soul to the first man he thought he could get me interested in, so that I would then want to drop Mel and go off with him into the sunset.

But Cindy wasn't done yet... she was just beginning...

"So it was my sister's idea to shut off the phones..." Cindy was talking quickly now.

"That's one for you... But how about your new 'boyfriend' Josie... Hmm?" Cindy's voice was crackling it was so angry, "Did you tell her all about him?"

"Look... Cindy, I don't..." I tried to answer, but was again shutdown.

"Yes he did..." Mel was speaking, "He told me all about him last night, and I forgave him Cindy... now dammit, what's this really all about?"

Cindy was still pacing in front of us, and the horrible and angry expression that she had started with was actually starting to fade into a more calm and controlled one.

"Ok, that's two for you..." She said cryptically, and then in a normal volume, "do ya wanna try for three Joscelyn?"

"Hmm?" she taunted, "Let's see what you have to say about... this!"

From behind her back she finally held up what she was so upset about. It was my Pagans Motorcycle Club jacket. Cindy's eye's glared at me, as if daring me to explain what this was all about. I never expected all these pieces of my life to come crashing together in one terrible nightmare. I let out a long sigh. This was getting out of hand.

"Well?" Cindy pressed, "Just how long have you been in a motorcycle gang?"

"Josie?" Mel was worried and needed answers, was she worried about trusting me?

Tears were coming now, I just kept thinking it would all work itself out, and it was the stupidest thing I could have ever done. I'd lost their trust now and I wasn't at all sure I could win it back... but I had to at least try.

"Now... let me tell you just what's been going on since Friday night!" Cindy said.

"It seems your buddy Roy, the one that wanted to rape you?" Cindy continued, "Has been out drumming up his gay stud buddies, saying that you pulled a knife on him and that you need to be taught a lesson!"

"And here's the funny bit, a couple of the guys he wanted to help him," she went on, "turned out to be Pagans! And when they heard your name as the one they were going to attack... instead went out and rounded up the rest of the Pagans, so that they could attack Roy and his friends, because they can't find you, they think he's killed you!"

"Right now, in our lovely little hamlet, there are around 80 well-armed twenty-something-year-olds on a mission to start World War III... because of YOU!" Cindy finished by pointing her index finger squarely in my face.

"Ha! And I'm out trying to get you into the Sisterhood?" Cindy screamed, "You are a real mess Jack... you're going to figure out your life RIGHT NOW!"

Cindy whirled on her heel and stepped to the front door. She opened it and simply said, "Ok guys, this way!"

I quickly jumped to my feet when I realized what she was doing, but it was too late, I had nowhere to go at that point in any case, and my fate was sealed.

Three very large men's frames came through the front door and into the Den. Each one had a Pagan's jacket. The first one was Billy, we shared the same birthday and he always insisted I ride with him. The next one was Smitty, my Tae Kwon Do instructor, and finally the floorboards cracked as the last one walked in, it was Tiny.

"Each of these men were afraid that you were dead Jack," Cindy was saying, "They don't have any idea what's happening here... maybe it's time to say something, huh?"

Billy and Tiny looked at me and smiled, both seemed to realize what was happening right away. I suppose with my build, it wasn't that outrageous. Smitty had to squint for a few minutes before he too seemed to suddenly recognize me.

"I... I'm sorry I worried you guys," I found myself saying, "You have always been there for me, and I should have leveled with you. I am beginning a long series of therapies that will eventually allow me to change my sex to female. Please understand... I just didn't know how to tell you this... and please forgive me for not being more open and honest about it with you."

Eventually Smitty started nodding his head, "Ok Jack, I get it now, we'll take care of letting the leaders know... doubt they'll want to interfere anyway... I wish you all the best of luck though!"

"Yeah like, hope it all works out as you want," Billy said, and then Tiny crushed me in his usual bear hug. When Cindy finally got the three Pagans out of her house, she came over and stood in front of me with her hands on her hips.

"I know Cindy..." I tried to explain myself, "I'm not perfect, and I tried to keep the best of all worlds for myself, which was really, really stupid... I'm sorry."

"Well... that's three for you!" Cindy replied, as the electricity in the room dimmed a bit and she was able to sigh, "Now, what the hell do we have for dinner?"

***

By the following weekend, Roy had stopped by my office to apologize, allowing the situation to calm down to almost normal. But Andy and I had a lot to make up to each other about. Eventually things got back to normal, but I didn't try any more male-to-male dates again, and probably won't for quite a while.

The Pagans wanted me to attend one last local fair, as they always volunteered to help raise money for various causes through that event. The fair went off without any problems and I made myself available for the water dunk contest seven times! By the time it was over, I was pretty wet, but had raised some serious cash for the day.

Billy offered to take me home, and we all rode screaming out of the fairgrounds and down the local highway. But just as Billy went roaring down the road, a state patrol car parked behind some bushes decided Billy had used excessive acceleration. This kind of thing seemed to happened all the time, and while most of the club went home, a few members snuck around behind the patrolman to make sure Billy and I were arrested and booked properly.

After pulling Billy and I over, the cop put me in handcuffs (why do I always seem to end up in these?) and then sat me in the back seat of his cruiser. But for Billy, he handcuffed him and made him sit on a curb. Billy looked over at me with a very serious look, and I knew what that meant. But there was just no way to be sure of this patrolman's intentions through all of this, so all we could do was wait. But I knew there were others following to be sure we were ok, and at least that was comforting. Suddenly another patrol car showed up, they put Billy in that car, and then left, leaving me in the original patrol car.

The patrol officer started up his cruiser, and flew out of the driveway we had been in. With his lights flashing, he was easily reaching speeds of 80-100mph. I was being thrown all over his back seat at those speeds and couldn't imagine what he was doing this for, but then I realized... he was losing my friends who had been following us! I had checked all my pockets, somehow my skeleton keys must have dropped into the dunk tank during the fair.

At the speeds he was going, it would be pretty easy to lose my friends on their motorcycles. But suddenly he disappeared behind a local market and just sat there for about a half-hour or so. He had shut off his lights and siren, and gradually pulled out into the street and was now driving at a more modest speed! I desperately looked back for any sign of our pursuers, but I only saw darkness.

After another half-hour of driving, he pulled into a tree lined area next to a lake. Getting out of the patrol car, he turned to the back door and opened it. He grabbed me by my ankles and pulled me onto my feet outside the car. He shut the door, then took the keys and went back to his trunk lock and opened the trunk lid all the way up. Leaning into the trunk, he came out with a 15" hunting knife.

For the next few minutes he seemed to get off slicing my shirt into long pieces. Gradually he tied up all the loose ends so that the fabric held my wrists up close to my neck. All during this he would brush my nipples with the sharp side of the knife.

Suddenly he yanked at my beltline with the huge knife dropping my pants down around my ankles. He then grabbed them and had me stand on one foot at a time until they were gone from my body. Now is when he let out a huge laugh, as all I had on now were my white silk panties.

"Well, aren't you just the prettiest thing!" he cackled.

Finally after running the point of his knife up and down the front of my panties he said, "You don't remember me do ya?"

I didn't look at him or acknowledge his question, I knew there was no rescue this time. And he wasn't the forgiving type.

"Your Daddy..." he said emphasizing the daddy, "got me demoted just because I didn't show up to one of his frikin' neighborhood safety meetings on time!"

"Now what do ya suppose," he continued, as he wiped the knife around my Adam's apple, "we ought to do about that."

He turned towards the car, then quickly pivoted back, slamming his fist into my stomach, but held me up with his right arm, and threw my middle over the cars left rear fender. I was bent over into his trunk trying as hard as I could to get another breath. He came at me from behind and cut a slit into the panties. Then spitting on his hand, he dropped his trousers as he pulled my legs apart.

He grabbed his fully erect member with his wet hand and rammed it straight into my asshole. The pain was just as bad as anyone who has had anal intercourse can attest when no lube is really used. I wanted to scream so bad, but couldn't get any decent breath going while I was still folded over the fender.

The funny thing was he kept his patrolman's helmet on the entire time, and I remember seeing it in the dusky reflection of the patrol car's finish as I thought, "what a jerk!".

Suddenly half of his helmet went tumbling across the trunk, between the open lid and the back window. Within a second I noticed the other half of the helmet falling into the open trunk. It had been split exactly in half! I managed to bring my head up in time to see the patrolman fall over on the ground, with Smitty standing next to him as he did.

My fellow Pagans had found me, after all.

***

It's still a hard incident to speak of, any rape is, for anyone. The smell of that attack has never left me, and I can smell that Patrolman even now. Once you have had to face that level of absolute violence, and know there is no escape, no second chance, no do-overs, then you will know just how deep your own level of survival goes, and you will be able to see your abilities multiply, and your own self confidence grow exponentially.

My attacker wasn't killed, but he was certainly put into a very embarrassing situation, that he was never able to live down, and eventually forced to quit the police. It's amazing what can be done with a little woman's clothing and make-up!

My friends knew just where to take me to get the best care in town, and Mel made it her duty to get me back to perfect health. Gradually I realized how poor my decisions had been in regards to the Pagans. But I still talk with Billy on Facebook, and will always feel privileged to have known them. In the meantime, Cindy is still working hard trying to get me initiated into the Sisterhood, and of course the Doctor is working hard to get me looking as feminine and possible and I'm loving every minute of it. Still plenty to do at school to keep me busy, and it gets crazy from time to time, but while this was the hardest time of my transition, it showed me just how much I really REALLY needed it... Cheers!!

Joscelyn2tg
Joscelyn2tg
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LisaBrooksLisaBrooksover 5 years ago
The Web We Weave To Survive!

Joscelyn after reading your responses to the feedback I can see The Pagans were a moment in time that benefited you and the members! You were there working on your own projects! No one knows what will become of the people in this story! I think Roy and the police officer were part of the disdain many have of trans women! It really disgusts me that they can act that way and some get away from their disgusting actions whether it be verbal or physical! Since you're writing your own story of your personal history every day shows your growth of becoming more and more feminine it gives us trans women something to look forward to! Maybe not as much angst!

Joscelyn2tgJoscelyn2tgabout 9 years agoAuthor
Re: What a Life

Thank you for your many compliments. I wrote this to pay back those who have helped me recover from problems I have been forced to deal with by accepting my true gender. I would tell stories of my early female years and when I asked how I could repay them for their kindness, the answer was always the same... write your story! Yes, much of whats in this Bio happened in my second year of a two year college. The only item in your list that I actually didn't achieve until a year later, were mult. prostate orgasms. I did try to explain the sex scenes in the story. While a sex act DID happen in each sequence of events where shown in the story, the actual sex was sometimes a little um... more involved than what actually occurred.

I have enough sexual experience to last several lifetimes, and I honestly don't understand why you would think this a good thing. Much of what I experienced was wasted on someone so young as I was. I'm glad you stayed "the good boy", as you will be sophisticated enough by now to appreciate what comes next. I love teaching what I know to others, and its why I became a Pro Dom, or Mistress. I developed sexually at an earlier age because I was female, and most females do. Losing virginity at 12, a pregnant girlfriend at 15, and on and on. Certainly nothing there to be jealous of, and really not much of a 'skill set'. I was fortunate to find people who where willing to guide my development and as I grew mentally, was able to see what mattered in life. Always value your family, friends and lovers, its our humanity we truly share in life, and reaching out to help others will always give you your 'highest rate of return'.

Being retired, I could care less who knows what about me anymore. When working for large companies, it is a problem being on these sites, as they tend to be less than happy about having their employees connected with them. So your paranoia is understandable, and I would suggest an anonymous email. Then contact me via my feedback page and maybe we can talk more. Cheers! --- Josie

AnonymousAnonymousabout 9 years ago
What a Life

This is one of the most impressive stories that I have ever read. The most amazing thing about it is that it is (mostly) true. I find it hard to believe that any real life could have as much adventure, action, and sexual experience in it as yours does. If I am correct, this chapter only goes up to your freshman year of college, yet you have done more than most people will do in their entire lifetimes (negotiated a major musical contract, sex in a private plan, multiple prostate orgasms in one session, thrown a man threw a window, etc). On the one hand, your story provides an excellent means through which I can live vicariously. On the other hand, reading this series is very painful for me, as just makes my own life seem all the more boring and depressing and my own skill set seem lacking. I have always been “the good boy.” I am now a high performing senior at a prestigious college, studying several technical fields, and have never even been kissed or “hit on." I am not trying to make light of your experiences. I know that you have darker times in later chapters (I still need to read them), but at least you have these great memories, and I believe things turn out well later. I can but hope that my life turns out half as well.

If my writing seems familiar, I have commented fairly many times before. I plan to get an account someday, but I am very paranoid.

Joscelyn2tgJoscelyn2tgover 10 years agoAuthor
Thank You So Much For Your Comments Anon.

Most of what you've said is true, but perhaps I did not explain enough. "Cindy" was very angry with me, as well as Andy, and Mel for that matter. She's a Dom, and a hothead, we both are. However she also knew many important people in the local community at that time, including policemen, politicians, etc. When she heard what had happened with Roy, and the continuing saga around me, she expected to find innocent reasons for why I was involved. I haven't been innocent since 1st grade, <sigh> and she was spitting mad, pushing to make me give up anything else she might not know of. So she went and did some digging of her own, and found my 3 good friends in the Pagans, finally realizing I was also. Didn't they deserve to know about me? They would have given their lives in an instant, but I couldn't tell them what I was doing because I had no clue what the Pagan leadership would say about me. (and as I figured, I later heard they made terrible threats towards me). That's who they were, and it got worse. Now... were those three incredible friends and do I owe them my life many times over? You bet!! But that does not change the fact that, overall, I made some poor decisions in regards to staying involved with the Pagans when I really needed to be giving 100% effort to transitioning (which is not clear in the story, but it was a promise I made to "Cindy"). Very shortly after all of this happened the Pagans were involved in VERY bad things, and thats all I can say here. "Billy" managed to get out of the gang before ending up in jail the rest of his life, but he was the only one. Everyone else from the Pagans of that time is either currently in jail or dead. Sound like the Pagans were a good decision? Sorry - thought it seemed obvious, but then, I'm too close. OH! and as far as the Sisterhood goes... better put your seatbelt on, its gonna be a bumpy ride!

AnonymousAnonymousover 10 years ago
The Pagans were good friends to have not bad ones. Not a poor decision.

I loved this chapter as well as the previous ones. Keep the chapters coming. But I think that your relationship with the Pagans was not bad at all. You ended up being kind of their mascot. You got to be their friend and helped them out and they kept you from getting beat up in school or bullied. They taught you self defense which you needed to help fight off Roy. The Pagans looked out for you and rescued you from the bad cop who wanted to hurt your dad but ended up going after you instead. You could have ended up dead if it was not for them in your life. Your father had enemies that you needed to be aware of. But the Pagans were not one of them. They were good for you then.

As for Cindy being mad at you for not telling her about the Pagans. She has not been exactly forth coming with what her plans for you are, and the Sisterhood. Cindy and Mel are being very tight lip about somethings in the short time that you have told your three friends about wanting to be a girl. And Cindy should have asked about your past if their was any problems that could affect your introduction into the Sisterhood. But if your timeline is accurate, much of this story has happened in a short period of time so far, and your past would have come to be discussed.

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