Chapter 38 -- Sherry's Dilemma II

Day after day, I must face a world of strangers
Where I don't belong,
I'm not that strong.
It's nice to know that there's someone I can turn to
Who will always care,
You're always there.
When there's no getting over that rainbow,
When my smallest of dreams won't come true.
I can take all the madness the world has to give,
But I won't last a day without you.

--I Won't Last A Day Without You (Carpenters)

Kristen left the bedroom, and I heard her tell Sherry to come into my bedroom.

Sherry entered the room quietly.

I smiled and asked, "Are you nervous?"

Sherry nodded. "Yes," she answered in that same monotone.

The truth serum was still in effect.

"Truth serum off."

Sherry blinked her eyes and looked very confused. "How did I get in here?"

Oh, shit! That was another side-effect of the tickets. Sherry was in the living room when I handed her the ticket, and she was now in the bedroom.

Quickly, I went to the drawer where I my tickets were stashed, pulled off a ticket and handed it to Sherry.

"Wha-" Sherry started before she received the ticket. "You have one wish."

"My wish is that you will understand that I know all about Tim Hawking and his wishes, and that you accept that I know this without fear or embarrassment. You will also not try to figure out how this compulsion happened, and you won't wonder about any time shifts that occur because of the tickets."

"Your wish is my command." Sherry blinked, and then said, "This is your bedroom."

"Yes, it is."

"Why are we here?"

"Sherry, you've been a very good friend to both Kristen and me. I understand your problem, and I want to help you with it. In return, I have a request of you."

"A request?"

"Yes. I know that you've been interested in me for quite a while. You proved that to me in the past year. I love you as a friend, and I want you to remain my friend. If there's anything that we would do that would make you think any less of me, I want you to tell me. OK?"

"What things?"

Instead of answering Sherry, I moved closer to her and kissed her.

A lot of thoughts ran through my head during that kiss.

Sherry was the probably the most difficult situation I ever had to deal with. She wasn't a raving beauty, but she was still a good looking girl. She also seemed to have a fixation on me that nobody--with one exception--ever had on me.

Sherry recently told me that Lynette understood how she felt about me because Lynette felt the same way about Kristen. I would have to say that Lynette was exaggerating. I felt that Lynette's attraction to Kristen was more to do with their personalities, and there was a reciprocity between them.

With Sherry, however, it was definitely a one-way thing. Her love for me was very much like a school-girl crush that she never grew out of. Sherry enjoyed listening to me when I played the piano, but I got the feeling that she didn't love me because of that. In fact, Sherry never really told me what it is about me that attracts her.

If I never interacted with Kristen, it's possible that I might never have found out about Sherry, and that's a bit of a shame. Sherry is a perfectly wonderful person in her own right. However, when I talked about her with Patty, Patty pointed out some things that would make me think twice about having Sherry as my girlfriend.

First, Patty said that the kind of crush that Sherry has on me could be dangerous. Sherry never seemed to get to the stage of single-minded determination to have me, but Patty said that such a crush would make Sherry extremely possessive of me if I were to ever return her love. She'd be jealous as hell, and would watch me like a hawk anytime another girl was around. Of course, Kristen was originally like that, and she mellowed out quickly. However, Kristen never had a crush on me the way Sherry did.

Here I was, in my bedroom with Sherry. She had a compulsion to perform oral sex on me. Instead of being excited by the prospect, I felt guilty.

I always like to think of myself as a nice guy. It's easy to blame assholes such as Tim Hawking who would take advantage of innocent girls like Sherry and force them to perform oral sex. Instead, I found that I was angry with myself. After all, I did the same thing with Patrice, Marla, and Kristen. The difference was that I was sorry that I fell into that trap, but the truth was that I didn't know how Tim felt. For all I knew, he could be extremely sorry about the way he behaved with the cheerleaders, although I have some difficulty believing that.

Now, Tim inadvertently put Sherry onto a collision course with me. This was a situation I originally wanted to avoid, but thanks to those tickets, I now had to deal with it.

Sherry was indeed a wild card, and she was a wild card that I needed to deal with alone.

Sherry opened her eyes after we kissed. I could see her emotions burning in her eyes, and I wondered if I made a mistake in even kissing her.

"You're afraid, aren't you?" Sherry asked.

I nodded. "It's not that I don't like you, Sherry..."

Sherry sighed.

Another ticket later, Sherry was intoning "You have one wish."

I knew that I could not totally undo the effects of a ticket with another one, but I learned that it was possible to mitigate the effects.

"Sherry, I wish that your compulsion to suck me off is toned down and could be satisfied by..." I suddenly changed my mind. I was about to say chocolate covered peanuts, but realized that I would be equating Sherry's problem with Kristen's. Thinking quickly, I added, "By simply playing with yourself."

"Your wish is my command."

I saw Sherry's eyes come back to life, and she squinted a bit.

"Something is different," Sherry said, shaking her head.

"Oh?" I asked, pretending not to understand.

All of a sudden, Sherry reddened, and it was apparent to me that Sherry knew what changed. I excused myself to go to the bathroom, leaving Sherry alone in the bedroom.

In the bathroom, I found that I was hard. Talking about sex had that affect on me... I'm only human. In addition, I found that giving away a ticket also made me hard. I wondered if it had anything to do with what Camille told me a few months back at Lake Shore Point. Anyway, I tried to will my prick down, but it wasn't any use. After a few moments, I simply washed my hands and left the bathroom.

I was shocked by what I saw. Sherry was on my bed, completely naked, with her right hand between her legs and her left hand rubbing one of her breasts.

Sherry saw me arrive, and instead of being embarrassed, she gave me a look of smoldering sexuality.

I watched Sherry, mesmerized by what she was doing.

It was my original intention that Sherry would be able to go home and relieve herself in privacy there. Instead, she was giving me a sexual show right in my own bedroom!

"What are you doing?" I asked, my voice cracking from my surprise.

"I... I'm not sure, but the feeling came over me all of a sudden."

Sherry made no attempt to stop what she was doing.

A part of me wanted to leave the room, and I started walking toward the door.

"No!" Sherry called out. "Don't leave me!"

Another, more powerful part of me wanted to stay. With Sherry asking me to, I stayed in the room.

This was not the first time that I watched a girl masturbate. Kristen would sometimes tell Lynette to put on a show for me, and then to suck me off and deliver my seed to Kristen, who would be waiting for Lynette in the spare bedroom. It was one of the games that the two girls liked to play when June wasn't around. Kristen knew that I enjoyed watching Lynette play with herself, and that Lynette seemed to get off on being told to do such things.

Without realizing it, I moved closer to the bed to get a better view. After Sherry noticed that I was staying, she closed her eyes and focused on her own pleasure.

Sherry's legs were spread wide, as if she were doing one of her cheerleader's splits. Her dark hair and right hand hid most of the action from me, but I was familiar enough with what was going on to be able to fill in the missing pieces mentally.

For about five minutes, Sherry continued to play with herself. For the first time, I noticed the nipple that Sherry was caressing. It grew from a tiny thing to more than a half inch in length. It was also thicker than her other nipple, which Sherry had not yet touched.

I moved closer to examine Sherry's breasts, curious about the growth of that nipple. This was a totally new experience that I never saw with any other girl. I mean, I've seen nipples get bigger when girls get excited and Wendy's nipples were enormous as well, but Sherry's seemed to grow from practically nothing to the biggest one I've ever seen.

Again, without realizing it, my body moved on its own volition. I bent down and took that enormous nipple into my mouth. Sherry's hand simply moved out of my way until it was caressing the hair on my head. A slight moan escaped her lips.

While I suckled at Sherry's nipple, my body moved to lay next to hers, and my right hand moved down her body until it was touching Sherry's right hand.

In my mind's eye, I could tell that Sherry was playing around her clitoris, touching above it, below it, and on each side of it, but never touching it directly.

My index finger touched her clit directly.

Sherry sucked in air as she felt my finger touch her tender spot. I continued sucking on her breast, playing with that huge nipple with my tongue.

Sherry's hand moved away from her legs, letting me masturbate her. I moved my finger up and down her slit, collected her secretions, and used them to make her clit more slippery.

I felt a tug on my pants, and then my zipper went down. Sherry tried to pull my pants down with one hand, but found that she didn't have the right leverage.

Without thinking of the ramifications, my left hand went to the other side of my pants, and together, Sherry and I lowered my pants and my boxers.

My dick throbbed as Sherry's fingers encircled its shaft and she started to slowly jack me off.

I was lost in a bunch of sensations as Sherry moved her hands in time with my own hand between her legs. I quickly found that if I quickened my pace, Sherry would quicken hers as well. I found that I could get Sherry to the pace that I wanted easily that way.

I heard Sherry moan, and felt her cunt get even slicker as her orgasm hit. It wasn't loud, but I could still tell that it was there. I continued to manipulate her, and she continued her hand job.

Suddenly, I felt Sherry's hand behind my head pull me closer. I sucked her breast harder and to my surprise, my mouth filled with fluid. The fluid wasn't salty, but sweet. It was as if Sherry was nursing me!

After a few moments on my tongue, I realized that I was definitely tasting milk from Sherry's breasts!

Despite Sherry's hold on my head, I managed to pull against her and off her breast.

Sherry was staring at me, a look of embarrassment on her face. Her swollen nipple had a bead of white fluid--her milk!--at the tip.

"Please don't stop!" Sherry asked. She gave me an embarrassed look and after a moment, she explained, "That happens, sometimes."

If Sherry was lactating, didn't that mean... ?

I pulled my hand from Sherry's legs and looked at the cheerleader with concern.

"Sherry, are you pregnant?" I asked.

Sherry shook her head. "No. I'm still... I mean... I never..."

"But your breast..."

Sherry sighed. "It happens. The first time it happened, I was really worried. I cut school that day and went to the clinic. Fortunately, the doctor there was a woman, and when I told her what happened, she told me it was rare, but not abnormal. She did run some tests to make sure there wasn't anything wrong. She made me... you know... coax my milk out so they could run tests on it."

This sounded very personal, and I was sorry to have Sherry tell me this. "I'm sorry, but I was surprised..."

Sherry gave me a warm smile. "That's all right."

I looked at the cheerleader on my bed. She was still lying there nude, and didn't seem to make any attempt to hide herself. I then noticed something else: there were a few spurts of semen on her thigh... I must have had an orgasm! I think I was so surprised by Sherry's lactation that I didn't even realize that I actually came.

Sherry followed my glance and saw what I saw. She took her hand and rubbed her finger on one of the streaks. Before I could protest, she brought the finger to her lips.

"Sherry, I'm sorry..."

"Don't apologize, Jim. I'm the one that made you shoot off."

"I mean, I shouldn't have touched you to begin with."

"I wanted you to touch me. I asked you to."

"I know, but..."

"Kristen knows."

Huh? "What do you mean, Sherry?"

"I saw the door open as we were... playing with each other. I saw it was Kris, and she quickly left when she realized that I saw her."

Fuck! I closed my eyes, wondering how I was going to explain this to Kristen.

"Get dressed, Sherry. This got out of hand!"

Sherry got up and went into the bathroom. I heard the water run, and I realized that Sherry was cleaning herself up. I saw that I still had semen on my dick, and found a box of Kleenex and used a tissue to clean myself. I pulled my pants and shorts back on.

Sherry came out of the bathroom, nude, but without any modesty.

As Sherry walked by me to pick up her discarded clothes, I handed her another ticket.

"You have one wish."

"I wish you will tell me the truth, and not remember anything that happens while you do are telling me these things, until I say 'truth serum off.'"

"Your wish is my command."

I needed to know some more things.

"Sherry, why did you masturbate in this room instead of waiting to get home and do it in private?"

"I am preparing myself to give my virginity to you. I need to get over my embarrassment over being naked with you. In addition, there was a lot of pent up need from my compulsion to suck you that when I realized that I could satisfy it another way, the feeling hit me like a ton of bricks."