He felt Jason’s hand brush and then gently grab his upper thigh. As they continued to lock lips, Jessie was very conscious of Jason’s hand which slowly crept higher and higher on his thigh until it was reaching under his skirt. Should he stop Jason? Was there any harm? He continued to passionately kiss him and got lost in the moment.

Suddenly, he could feel Jason’s hand under his skirt and around his backside. Jason was tracing Jessie’s panties with his fingers. Jessie jumped back a little. This was getting too out of control!

The Softening of Jessie
Part 40
By AshleyTS

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The foursome ate their late lunch and chatted for quite a while.

Jessie was getting accustomed to him and Jason being friends again. It was just like old times …only with the added bonus of a definite attraction.He noticed that Ashley and her man had been kissing and seemed very much into each other.

“Hey, we’re going to go hang out in my SUV.” Steve said as he grabbed Ashley’s hand and departed.

“Hey wait up Ashley!” Jessie yelled.

“What’s up Jess?”

“Why are you going to his SUV?”

“Well, we wanna make out in privacy. You can join if ya wanna. I mean, do you want to make out with Jason?”

“I’m kinda nervous to. Maybe we could just chat in there?”

“Sure, ok, grab him and let’s go.”

So they all headed to Steve’s SUV. Jessie and Jason jumped all the way to the back two seats while Steve and Ashley sat in the middle seats.

“Wow! Nice and cozy back here!” Jason stated. He felt a bit nervous sitting so close to the pretty girl. “Yeah, sorry am I cramping you too much?"

“No, not at all. You can get as close to me as you like.”

“I really like the way you’re styling your hair Jason. I like it a little longer.”

“Thanks.” Jason replied. He wasn’t sure if she even knew what he looked like with the buzz cut he was so fond of in the past.

“You know Jessica, I need to admit that the outfit you have on today is insane! I mean that top and your skirt... sorry, but I just really think you look beautiful. I’m just... not that good with words.”

“It’s ok Jason. I know what you mean. Actually, your sister let me burrow everything I have on so you should thank her.” Jessie replied beaming from the compliment.

“Ummm, Jessica, do you mind if I give you a kiss?”

It was the words Jessie hoped he would hear!

“I would like that.”

With that, their two lips embraced. Electricity filled the SUV as their hormones raced.

Jessie scooted closer to Jason and put his arms around him.

He felt Jason’s hand brush and then gently grab his upper thigh. As they continued to lock lips, Jessie was very conscious of Jason’s hand which slowly crept higher and higher on his thigh until it was reaching under his skirt. Should he stop Jason? Was there any harm? He continued to passionately kiss him and got lost in the moment.

Suddenly, he could feel Jason’s hand under his skirt and around his backside. Jason was tracing Jessie’s panties with his fingers. Jessie jumped back a little. This was getting too out of control!

“Oh, sorry…did I go too far?" Jason asked. He was very concerned.

“Yeah, I think so. I’m just not used to this is all.” Jessie replied. He definitely was not used to having this kind of attention from another boy!

“Ok, we can stop…um, that was great though.”

“Yeah, it was. Are you mad?’ Jessie asked hoping Jason was OK with him stopping the wandering hand.

“Yes, I’m totally fine.”

Jason was such a cool guy! Jessie’s eyes glanced at Jason’s lap. Wow, he had a huge bulge in his pants. It was then that it clicked. The reason Jason was getting hard-ons was because of him! Jessie’s changed body was exciting Jason! Although Jessie felt a bit awkward at this thought, it was very flattering. He could do this to Jason??? Pretty cool!

“Um, you seem to be pretty excited.” Jessie stated in a humorous tone as he glanced down at Jason’s pants.

“Yeah, sorry, I couldn’t help it. Like I said, you look incredible!”

Jessie knew that he himself had had numerous hard-ons in his life but he couldn’t recall the details. He thought of his own penis and couldn’t imagine his member tenting up his skirt the way Jason’s was tenting up his pants. Jessie found Jason’s bulge intriguing. He knew that it shouldn’t be anything special since he had a penis of his own, but he couldn’t take his eyes off of it. Why couldn’t he remember any details about having a penis? This all seemed so new to him and he had so many questions.

“Ummm, so what do you do when it is so big like that?”

Jason kind of figured that his pretty friend had little experience in this department which made him happy as he was only way too eager to educate.

“Well, I either have to whack off or else I just have to let it go down and do nothing.”

“What happens if it just goes down? You kind of look like you are uncomfortable.”

“Oh, it gets very uncomfortable if nothing happens. Ever hear of ‘Blue Balls’?”

“I don’t think so. I don’t have any balls.” Jessie replied. He used to have balls didn’t he??? He just couldn’t remember!

“Well, let me try to put it in perspective for you. Imagine putting on a really great dress, doing your hair all up all pretty and getting ready for a date. Then the guy doesn’t show up. That big letdown you would feel is what happens when a guy doesn’t finish.”

Well that did help Jessie relate…wow that must suck!

“Why don’t you ‘whack off’ then and get it over with?” Jessie asked.

“You don’t mind?”

“No, I mean it’s no big deal.” Jessie replied. He knew that they were both boys and it didn’t matter. Plus, he was very curious.

“OK, promise you won’t laugh ok?”

“Promise!”

With that, Jason unzipped his pants and pulled them down a bit. He was having a hard time containing his excitement. The very thought of the pretty girl watching him was almost too much.

“Wooowwwww!!!” Jessie gasped.

There was a definite difference between Jason’s penis and his own. It was huge! It must have been at least 5 or 6 inches long! He wondered how sizes could be so dang different! How could some boys have big ones like Jason and some have  ½” inch ones like him??? He thought about it for a second before realizing that he didn’t care to have one as big as Jason. It was fine on Jason and looked good on him, but Jessie kind of liked how his crotch looked flat and smooth in clothes.

“Have you ever seen one before?” Jason asked looking at Jessica whose wide eyes told the story.

“Of course I have silly. Yours is just really big!”

“Thanks!”

“So what now?”

“Hey Jessica, do you want to help me get off? You can say no, but it’s totally safe.” Jason asked keeping his fingers crossed.

That was an odd offer! He knew that he had masturbated in the past but he never helped another boy get off. He wanted to say no but found himself way too interested to decline.

“Ok, don’t worry, I’m a pro at this one.” Jessie replied with confidence.

He timidly touched the penis. It was so hard! He backed away for a second before reaching for it again. Dang! He had done this to himself so many countless times in the past but couldn’t remember how to masturbate. Jessie picked his brain trying to unfold the mystery to no avail. He was drawing a blank…how could he forget how to stroke himself???

“Do you need some pointers?” Jason asked her. She seemed completely lost.

“I know I know how to do this. I can’t remember. I’m sorry.”

“It’s ok Jessica. Here let me show you. Firstly, here’s some tissue for when it happens. Make a large ring with your thumb and first two fingers just big enough to snugly fit around it. Good girl. Now don’t squeeze too hard but use gentle pressure and work you hand up and down my shaft. There ya go. You’re doing great!”

This was so new to Jessie and so very exciting at the same time. He wondered what Jason meant by giving him the tissue. Was something going to happen to Jason’s penis that required a tissue? Maybe boy’s cry when they get off? He couldn’t figure out what the tissue could be for.

“Now focus on just the upper part Jessica and move up and down faster.”

Jason was beyond ecstasy. He looked at Jessica’s shapely legs and the way her skirt gently draped over her lap. Look at those pretty painted fingernails touching him so intimately. Her face looked so beautiful! His eyes moved to her breasts. With Jessica stroking him more aggressively her breasts jiggled back and forth, up and down.

“Am I doing good?”

“Amazing…I’m getting really close girl!” Jason exclaimed. He was trying to hold off and extend the pleasure but this was all way too much.

“Okay!” Jessie replied having no idea where this was leading.

Jason stared at Jessica’s breasts and their supple sway in her bra and that did it.

“Ok, use the tissue…I’m going to cum!”

Jessie noticed that Jason’s hips tensed and raised up off the seat and he seemed to freeze. Use the tissue?!?!? What was the tissue for?!?!? Suddenly something shot out of Jason’s tip. Jessie panicked! Jason quickly grabbed her hand which held the tissue and covered his penis trying to catch all the cum.

“Why didn’t you use the tissue Jessica?”

“I didn’t know what to do ok?!? This is all new to me!” Jessie said panicked. He never could have expected that a boy’s penis would do that!

“I’m so sorry girl. I didn’t realize it was that new to you.”

Oh crap! Jason saw where his first spurt had landed and it was not good. There it was. The sticky substance clung to Jessica’s hair.

“What are you looking at?” Jessie asked as he reached for his hair.

He felt the sticky substance which was entangled in his pretty hairdo. He freaked!

“What’s my mom going to think? Get it off of me! You ruined my hair!” Jessie yelled and teared up instantly.

“Hey Jess, calm down. I’ll get it out of your hair.” Ashley said as she overheard her panic.

“Jason, how could you let this happen? That was mean!”

“I thought she at least knew a little about sex. I’m sorry Jessica.”

“Here, let me take you to the girl’s room and get you cleaned up.”

The two headed out of the SUV and Ashley used a damp towel to get everything out of Jessie’s hair.

“You really didn’t know that he was going to shoot his load everywhere?”

“No, how was I supposed to know that? I’ve never seen a penis like his before. Mine is way different. I mean mine doesn’t grow big and definitely doesn’t shoot stuff out!”

Ashley once again felt sorry for how emasculated Jessie had become. Every ounce of maleness had been stripped from him. He didn’t even remember masturbating anymore and that must have been a very strong memory to lose.

“Hey sweety, let’s head back home. You’ve had a long day oO?”

“Ok”
 

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To Be Continued...