Not a Man Ch. 03

"You should know about Sarah's husband—" started Tess.

"Ex-husband!" interrupted Sarah.

"About her ex, Luke. He was a real piece of shit, screwed around with tons of women. Sarah caught him, though, and that's when she decided to make him pay."

Sarah placed a soft kiss on my neck, and a shiver ran up my spine. One of her hands slipped under the panties, and her fingertips brushed over my quickly stiffening dick.

"You wanna tell him what you did?" suggested Tess.

"I broke him, piece by piece," Sarah whispered in my ear. She gripped my dick with two of her fingers, and started stroking it. "He begged me for forgiveness on hands and knees after I found out, so I started making him wear women's clothes around the house. He wasn't as pretty as you, though, he was a fat bastard. He thought it would end there, but I was loving it. Started calling him Lucy, even in front of his friends."

Sarah stroked even faster, and I saw her other hand disappear in her own pants. I couldn't believe a total stranger was jerking me off, just like that. She was pretty good looking for her age, and if circumstances had been different, I might even have enjoyed it.

"Then I went out and bought a strapon. He didn't like it, but I told him he had to suffer a little if he wanted forgiveness. God, it felt so good to slide that thing into him, and just really go to town on his ass. He squealed like a little piggy."

Tess pulled out her phone, and started recording. Sarah's jerking started to have a real effect on me, and my breathing got shallower.

"I fucked him like that for half a year almost, and I think towards the end he started enjoying it, too."

Sarah began nuzzling my neck, leaving big, wet patches on my skin.

"Wh—what happened at the end?" I asked, feeling my pulse race. I was getting closer, and closer to cumming.

"I got tired of her fat ass, and decided to go out in style. I dressed her in her finest clothes, and invited Mark over to our house. Mark was Lucy's best friend, for over forty years. He was the best man at our wedding. He's the godfather of our son. I put a blindfold on Lucy, and oh god," Sarah moaned, "I put a blindfold on her, told her it was a surprise, and asked Mark if he wanted to fuck her. His best friend in the whole world, but when he saw Lucy dressed like that, he... oh, fuck, fuck, fuck..."

Sarah suddenly collapsed to her knees, and furiously rubbed her her pussy under her pants. "Oh jesus christ lord have mercy fuck fuck fuck fuck FUUUUUUUUUUUCK." Her whole body shook with one incredibly powerful orgasm, and I was mesmerized by the intense pleasure visible on her face.

After what seemed like minutes, she pulled out her hand, and opened her eyes, an incredibly happy look on her face.

"Oh wow, I almost forgot how hard those memories make me cum," she giggled, tried to stand up, but fell backwards on the bench.

"Go on, finish the story," urged Tess. "I think someone's really excited to hear the end."

Sarah hooked her hand into my panties, and pulled me down. I stumbled, and fell backwards towards her, landing hard with my ass between her spread legs. She pulled me close to her, and pressed one hand up against my mouth.

The hand was wet, and bore the unmistakable scent of her pussy. She pushed at first one, then two fingers inside my mouth, and I tasted her juices. With her other hand, she started stroking me again.

"Mark was really eager to fuck her tight hole. My ex was really surprised to feel a real cock push inside of her ass, but with the blindfold on, she couldn't see who it was. Mark pounded him for five, six minutes, and Lucy squealed the entire time. Her little dick even got hard while she was being slammed."

I was getting close to my own orgasm, just a few more seconds. Sarah had removed her fingers from my mouth, and I was eagerly lapping at the juices on the palm of her hand.

"I wanted him to see who it was, though. I wanted him to see his best friend fuck his ass. I jerked him off, just like I'm jerking right now."

Sarah picked up her face significantly, and the first tingles of climax formed in my balls.

"I took off his blindfold, and he turned around, and looked his friend in the eyes, and then he came."

And then, I came. I closed my eyes, and let the orgasm wash over me. Fireworks exploded throughout my entire body, and spurt after spurt of cum shot out of my dick. For a few brief seconds, I was king of the world.

"He looked so shocked to see his friend, it was glorious. Mark kept fucking, until he came inside of my ex. I watched Mark's cum run out of Lucy's asshole, when I told her I wanted a divorce."

I opened my eyes again, and saw the mess I had made on the floor. I couldn't believe just how much cum I had produced. Tess was still recording the whole thing on her phone, but at that moment, I didn't care. I relaxed back into Sarah's embrace, while she kept playing with my softening cock, and nuzzling my neck.

"God, that was hot," commented Tess, and Sarah laughed.

"I'm actually kind of jealous you get to be the one to corrupt this little sissy. You don't happen to need my help, do you?"

"No, but I promise I'll lend her to you sometimes," Tess offered, and put down her phone. I couldn't believe she was just talking about me like I was a doll.

"That sounds great. Do you know who's going to be the one to break her in?"

"Yup. My boyfriend Jay. Hold on."

Tess picked up my pants, and pulled my phone out of the pocket. She tapped it, and Jay's cock filled out the screen. Sarah took the phone, and looked at it in awe.

"Damn, that's a nice dick. You are going to be one lucky girl," she whispered in my ear.

Sarah's hand disappeared, and she pushed me up. Just like that, the spell was over, and the usual post-orgasmic clarity set in. I couldn't believe all of this was really happening to me. It seemed too unbelievable, and if I hadn't been able to see myself in the mirror, I might not have.

"I... I think I'm gonna get something to clean up his mess," announced Sarah, and quickly walked out of the door.

"Is that story really true?" I asked Tess incredulously.

Tess laughed. "Well, some of it is, anyway. She's embellished it a LOT over the years, though. I met Lucy once, and she wasn't as reluctant as Sarah made it out."

"How long have you known her?"

"Six... seven years-ish? She used to tell that story to anyone who asked, and I always wondered what kind of person would just let themselves get turned into a woman like that. Then I met you, and now I know. I almost didn't believe my luck when Jay told me what he wanted to do to you."

Sarah came back in the room, towel in hand. She dropped it on the wooden floor, walked up to me, put a hand on my hip, and drew me in for a fierce kiss. Her lips and tongue were like forces of nature, overpowering me with an animalistic frenzy.

It was nothing like the ones I've had with my girlfriends. It was powerful, and sensuous, and full of energy, with decades of experience backing up every movement.

Sarah drew away, and left me standing there with my eyes closed, mouth agape, breathless, begging for more. It was the best kiss I have ever had.

"Thank you, doll, for letting me relive that moment with Lucy," Sarah exhaled.

"What, don't I get a kiss?" quipped Tess.

"Of course, my dear," responded Sarah. "Why don't you clean up in the meantime, Henrietta?"

She sat down sideways in Tess' lap, and draped her arms around her neck. Their lips met, but it wasn't like mine had been. It was slow, and sensuous, filled with a certain familiarity. Sarah broke it suddenly, looked at me, looked at the ground, and very clearly signaled with her eyes what she wanted me to do. I knelt down, and picked up the towels, while the two of them resumed kissing.

There were three long, gooey ropes of cum, reaching almost all the way to the mirror. By some minor miracle, they had avoided the three piles of clothing that had formed. The one of clothes I was going to keep, the one I wouldn't, and the much larger one of things yet to come. Kneeling down, the added weight on my chest made itself noticeable, and I realized I had almost forgotten I was wearing the insets. I quickly wiped up the mess, accompanied by the smacking of lips, and soft moans behind me.

"Now, it looks like we still have a ways to go," announced Sarah, just as I finished my task.

The atmosphere was completely different between us, from that point on. After what she had done to me—no, what we had done together, I didn't feel embarrassed in front of Sarah at all. In fact, I was actually having fun for the first time in several days, like I was in a living dream.

Sarah kept handing me different articles of clothing, and I modelled them in front of the mirror. Tess giggled a lot, especially when I wore a ridiculous jeans skirt. I don't think I've ever worn more clothing in one day. Skirts, both long and short, t-shirts, blouses, jackets, sandals, sneakers, dresses, tank tops, thigh high socks, and even high heels, although I nearly sprained my ankle when I toppled over. Sarah went out into the store several times, coming back with more and more clothes.

I totally forgot about Jay, I forgot about Lifelast, I forgot about the blackmail, and I forgot about all the humiliation. I felt like the three of us have been friends for years, and I felt like I was just one of the girls, going out and having fun.

I felt like I belonged, in a way I've never felt before.

In the end, Tess picked out a pair of sandals, two pairs of shoes, nearly a dozen socks, just as many panties, including the "slut" one, a long, and a short skirt, three t-shirts, two blouses, two jackets, three bras, including insets, a sweatshirt, a purse, and last but not least, one incredibly beautiful cocktail gown.

Tess decided that I should keep on the slut-panties, and bra under my old clothes. Sarah rang up all the items one by one, and I watched the total sum steadily increase. I handed over my credit card to Sarah, and took a deep breath when the total came to $1,342.18. That was my video game and tech budget for several months, gone in a second.

Spent on women's clothing. Women's clothing for me to wear. It was still a hard concept to wrap my head around.

Sarah procured six bags with the store's logo imprinted on them, filling them with all the merchandise. Tess and her chatted a bit, and promised to call each other soon, but my mind was still in a haze, trying to process the last few... how long had it been? I pulled out my phone, was greeted by Jay's cock, and realized with a pang that I should have been back at Lifelast five minutes ago. Darla would be pissed.

"Thanks for coming, Tess, and it was really nice to meet you, Henrietta. I really hope we meet again some day," Sarah said, stuffing the receipt in one of the bags.

"I... I'd like that," I replied, thinking about the incredibly wonderful kiss.

"Don't worry, I'll make sure you get a turn," promised Tess, and then we left.

The bags were heavy, and we had to split the load between us, with me carrying the lion's share of four of them. We made a quick stop in the mall's food court, ordering some greasy fast food to wolf down.

On the walk back to the car, I noticed all the commiserating glances from guys who were there with their girlfriends or wives. Glances that portrayed distinct meaning of, "Oh boy, I hope my wife or girlfriend doesn't plan on buying that much. Must suck to be you."

None of them knew that it was all for me. Henry Newman, soon-to-be über-slut, according to Jay's plan.

WIth every step, the fog clouding my mind dissipated, and reality came back. The worst realization I made was that for nearly an hour, I hadn't been forced to pretend I was a woman. I had been a woman, at least in my mind. Trying on clothes, goofing around, laughing, having fun... as a woman. If it were just Tess, and Sarah, no Jay, I might actually like the whole thing. That thought scared me.

"So, what did you think of Sarah?" inquired Tess, after depositing the bags in the trunk of my car.

"I really like her," I answered honestly, her lips still at the forefront of my memory.

Tess laughed out loud. "Of course you do, the way she treated you. I don't blame you, she's an incredible woman."

"I actually had fun," I admitted, quietly, once we were on the road.

"Good, I'm glad to hear that. It doesn't have to be all bad, you know. You'll get used to it."

"What do we do now? I should have been back at Lifelast fifteen minutes ago."

"Yeah, that took a little bit longer than I expected. But since we're late already, do you mind if we make a quick stop on the way?"

"Sure, I guess. Darla's gonna be pissed."

"That old bat? Don't worry about her, she's all bark, and no bite."

"She threatened to write me up yesterday because I was late."

Tess barked out a loud laugh. "I have a friend in HR. Darla has tried to write up so many people, they just ignore her reports these days. Straight to the trash."

"Really?" I asked, amazed.

"Uh huh. Like I said, don't worry about her."

"In that case, sure."

We drove in the direction of downtown, and I was curious where our little detour would take us, but Tess seemed to be in a different mood. She seemed broodier, and pressed her lips together, as if she were in deep concentration. I thought it best not to disturb her.

Even if I had a problem with our destination, Tess would probably just ignore any of my concerns anyway. That seemed to be the trend, at least. In a way, it was kind of relaxing, too. I didn't have to worry about making any decisions. Well, there was of course one decision still up to me: how hard I was going to fight to stay a man. And my new name, because I definitely did not want Henrietta to stick.

Tess pulled into the visitor's parking lot of St. John's Hospital, and my curiosity intensified. My first fear was that she had somehow arranged for them to operate on me, cutting off my penis, but I doubted that there was a hospital in the country that would actually do that. Then I saw her face, and felt bad about even thinking such a horrible thing about her. Something troubled her, and she didn't appear like she was even aware I was there.

"Henry... would you mind accompanying me?" Tess asked, after the car came to a halt.

"Of course," I agreed without hesitation.

We got out, and Tess was like a completely different person. Her usual air of bubbly charm had fallen to the wayside, revealing a stoic, brooding figure. It was obvious she had been there before, because she led us straight to the elevator, hitting the button for the fourth floor. A few people entered behind us, and we made a stop on every level.

"I'm here for Mrs. Hopf, room 409. I'm her daughter. Can you tell me how she's doing?" Tess asked at the nurses station.

"There's been no change, ma'am," replied the young nurse.

"Thank you."

We walked around the corner, and Tess knocked loudly on the door to room 409, opening it without waiting for more than a fraction of a second. I wondered if I should stay outside, but Tess held the door open for me.

The room was fairly small, occupied by two large beds. One of the beds was empty, although it looked like it had been very recently used. In the other bed lay a frail, old woman, connected to several beeping machines. She looked incredibly small, and her face sunken. The hair on her head was the same shade of brown as Tess', although short, and wispy.

"Hey, Mom," greeted Tess, putting on a fake smile.

Mrs. Hopf opened her eyes, and it took her nearly a minute before she recognized her own daughter, but when she did, her eyes lit up.

"Theresa, I'm so glad to see you," she beamed. When she smiled, I could see the resemblance to Tess clearly. She had the same, beautiful face, only older.

Tess rushed over, sat down on the side of the bed, and hugged her mother as best as she could. Over Tess' shoulder, Mrs. Hopf noticed me for the first time.

"Who's your friend?" she asked.

"That's Henry, he works with me," explained Tess, and it actually felt weird for a moment that she was talking about me like I was a guy. No, I corrected myself, I was a guy, and it should have been weird for her NOT to talk about me that way.

"Is he your boyfriend?" Mrs. Hopf inquired in a typical mom-fashion, and I might have blushed a little.

"No, he's just a friend from work."

"Shame, he's kinda cute. Not like your usual boyfriends."

"I didn't come here to talk about my dating life, Mom. How are you doing?"

"I'm fine, dear. Feeling a lot better," assured Mrs. Hopf, but Tess didn't look like she believed it for one second.

"How are the doctors treating you?"

Mrs. Hopf started talking about her routine, and I leaned against the wall, trying to give them some space. Tess asked her about her medicine, about what the doctors said, about what the nurses said, and on, and on. From what I could gather, the doctors didn't have much to offer, which wasn't good news. If Mrs. Hopf were to be believed, though, she was about to get up at any moment, and dance around the hallway doing cartwheels.

"Tess, dear, when can I finally go home?" asked Mrs. Hopf after Tess ran out of questions, and Tess immediately stiffened.

Tess turned around to me, and asked, "Henry, could you leave us alone for a moment?"

"Of course," I mumbled, and retreated to the hallway.

There were a few chairs in the hallway, and I took a seat. I pulled out my phone, tried not to stare too long at Jay's cock, and checked the time. An hour late. Even if Tess were right, and Darla's complaints were just ignored, she would still go ballistic on me. I caught myself tapping my foot, waiting for Tess to return, and forced myself to stop. It was quite obviously hard for her to come to St. John's, seeing as how she had never mentioned anything about her mother in the months prior, back when were still just friends.

After five minutes, Tess emerged from the room, her eyes red, and her cheeks wet. I shot up immediately, and Tess threw her arms around me, burying her face in my shoulder. I held her, while she cried, and tried to comfort her as best as I could.

"Thank you for coming, Henry," she sniffled. She still held on to me, even though she had stopped crying.

"No problem, Tess."

"Sorry you had to see me like this."

"What's wrong with her?" I inquired.

"Cancer. Terminal. The doctors said she either has a few weeks, or a few months, but that's it. Everytime I come to see her here, she looks worse. I hate it. I fucking hate seeing her like this. She's only fifty-three, but she looks so old. I try to see her as often as I can, but it saps the energy right out of me. And when I don't go, I feel guilty about not being there for her. Dad's here every night of the week, at least.

"The worst part is when she wants to come home, and I have to tell her she can't. I have to tell..." Tess sniffled, "we can't afford to hire someone to take care of her full time."

A minute later, she disentangled herself, and we headed towards the elevators. On the ride down, it occurred to me that she had pressed her fabulous body up against mine. Her beautiful, round, and soft tits, separated by a fraction of an inch of cloth. A split second later, I felt like a massive pervert for even thinking about something like that at that moment. It was one of the very, very few times in my life I was glad my dick wasn't big enough that anybody would notice my erection.

"Do you want me to drive back to Lifelast?" I offered, after we validated our parking ticket.

"No thanks, Henrietta. You'll probably drive off the road, fantasizing about your new girlfriend fucking you in the ass, like she fucked her husband."

It was back to business as usual.