My Summer as a Girl Pt. 05

I returned home from my trip to school and visiting my counselor Miss Ignozzio to find Peter in the living room with my Aunt Janey. The two were incredibly casual on the couch, and I started to wonder just what it was between the two of them. Peter started to say something, but I waved him off as I had to race to the bathroom. It had been three hours in the car and I hadn't stopped.

As I was coming back into the room, I overheard a little bit of what they were saying. It was Peter's voice. "I'll leave it to the two of you, but we're going to need to do both. I'm just letting you choose the order."

"Choose what?" I asked.

Aunt Janey answered me, though I could tell that Peter wanted to. "It seems that Peter is getting a lot of feedback on our videos. A lot of it is good, but there are some issues."

"Issues?" I started to say.

Aunt Janey held up her finger to ask Peter for another minute, and she continued. "It seems there is a lot of chatter about whether or not you're a girl. The fans really want to know. So Peter is saying we are going to have to reveal that Molly isn't a girl soon. But they also want to see us perform a particular act. So Peter is saying that we can decide which one goes first."

I was going to interrupt her again, but I figured I should just let her finish. Peter seemed to think the same as we both watched Aunt Janey. "Sweetie, they want me to fuck you with a strap-on. I mean, it is what men like to see lesbians do."

OK, that was kind of a stunner. Now they were both watching me, and I was a deer in the head lights. I didn't answer, so Aunt Janey did. "OK, Peter, it's decided. We'll do the anal first and the big reveal second."

I wanted to speak, but I was dumbfounded. Peter started to walk out, but as he opened the door, he said, "Alright have it your way. I think it's a mistake, but I let the talent make decisions like this."

I was glad he left, because we needed to talk, but how to start this conversation? Aunt Janey patted the couch next to her and I dutifully sat down. I knew she was going to talk me into this, but I sat there and let her.

She hit me with those big blue eyes, and I started to melt. She smiled, knowing her power over me, and honestly liking it a bit more than she probably should have. "Sweetheart, think of it this way. If we do the anal first, while your gender is questionable, it will be a big deal. Molly's First Anal Experience. It will be a great show and the hype will work for us. Then later, we do the whole Molly's Big Reveal, and it too will be a big hit. If we do the reveal first, I don't see how your first anal will get the same sort of excitement."

Her logic was sound, but I wasn't all that sure I cared about logic right now. Other than a wet dream or two I had never considered anything entering my ass. No question, I was scared. Aunt Janey knew just what to do. She moved closer and started stroking my hair. "Come on baby," she said tenderly. "Let's get you upstairs and into costume. We'll film the advertisement for the bit, and you'll feel a lot better."

Over the past weeks, we had gotten a lot better about getting me into my Molly costume, but still, I loved it when she did. Aunt Janey would pamper me and make me feel so special. Because I no longer had any hair below my neck, it went a lot quicker, but she wanted to make certain my tail end was up to snuff. She cleaned me there especially good, and I have to admit, it really turned me on. I was still nervous about this whole thing, but I was excited too.

Aunt Janey had me kneel on the edge of the bed, the corner that had all the best camera angles. She checked the video and had me hunker my rear down a bit. We talked about my legs being off the bed, but with my knees under my chest, and me as low as I could go, it showed off my ass while completely covering where my vagina should have been. Plus, the angles were great - at least that's what Aunt Janey said.

Aunt Janey told me not to even bother talking; she was going to handle it all. She turned the cameras on to record and began talking to them. "Guess what we just found out? Our little Molly here is an anal virgin. Yeah, you heard me an anal virgin! So guess what we need to do? We need to pop that cherry! Do you want to be part of our live performance where we promise we will pop that little keister open and get right in there? You want to see me take my strap on and fuck Molly up the ass for her very first time? You know live is going to be so much better than recorded. So don't miss the further adventures of Janey and Molly when we pop her anal cherry. Doesn't that ass look cute?" Just then, she slapped me on the butt really hard. I yelped a bit, but fortunately I sounded like a little girl, so it was going to be OK without edits.

She stopped the cameras and she started looking at the footage to see if we needed more takes. As I watched over her shoulder, I saw that her slap on my ass had left a red welt. She spent some time editing, and I went to eat. When she showed me the finished version, she was using all three camera angles. She had redubbed the last time she said "pop" with a really loud popping sound, and she had zoomed in on my reddened butt. Honestly, if I had been sitting in my dorm room and saw that ad, I'd have ponied up the money to watch it live.

The next day was so normal it was almost a letdown. There wasn't much to do, so we sat around the house watching stupid movies and drinking wine. Aunt Janey had really changed her wardrobe since we'd become Janey and Molly. She walked around the house mostly naked most of the time, and the other times she was fully naked. She loved the affect it had on me. I couldn't look at her without getting hard, so I was hard a lot!

The next day was Friday, so tonight was our big live shoot. We started about 1:00 in the afternoon, getting ready. When she told me it was time to get ready, I got myself into the chair and expected her to start doing my make-up. Yeah, that didn't happen.

She called me into the bathroom and stood there with what almost looked like a beer-bong. What did I know? I'd never seen an enema bag before. I don't want to talk about it, but she made me do it three times - once with soapy water and twice more to get all the soap out. I guess it was that important because we didn't want anything showing on the videos, but not my happiest day at Aunt Janey's!

With most of the afternoon still open, she wanted to practice. I of course balked, but she said it was going to be a lot sexier if I was more at ease with what she was doing to me. Usually "at ease" meant a stiff glass of whiskey, but today she was following another route.

We went into the bedroom and I laid down on her bed. The cameras were off (I checked). She got some sort of lubricant that seemed to smell like strawberry. Not a good strawberry - sort of like cheap strawberry candy. She put a little on my anus and rubbed it around to get it coated. I was sort of happy I was laying on my stomach, because my cock sprang to life like I never expected it to. I was really embarrassed about being this turned on, but Aunt Janey kept it up with her chill, calmed approach.

I was way too much in my head about the boner and I really didn't feel her fingertip actually enter me. I just felt her moving it around. I guess she was spreading the lube on my inside walls. I certainly didn't hurt; maybe because I hadn't tried to get all tense in anticipation. I tried to stay relaxed, well as relaxed as you can be with a raging hard-on poking you in the stomach.

She just used her finger for a couple of minutes, then I felt her pull it out. Yeah, I was disappointed. I was growing to like the feel of her finger coating me with lube. She got my attention, because I was highly distracted, and showed me a little vibrator.

"See?" she asked me. "It's barely bigger than my finger. You're barely going to feel it." The problem was, I did feel it - and it felt great. She slowly stuffed it up inside me, but unlike her finger, this did feel like it was filling me. Then it started buzzing, and I jumped a little bit.

"Sorry", she apologized. "I should have warned you before I did that."

I guess I said something like that's OK, but I wasn't really making a lot of sense. I was kind of trippin' on the vibrations. This was a feeling I had never had, and I don't know that I can describe it. It felt good, new but good. It clearly was triggering something in me I hadn't expected. It was like something I had missed getting and really liked having again, but I'd never had it to remember it in the first place.

When the buzzing stopped I think I kind of jumped again. She just patted my ass and reached down for a bigger dildo. I knew it wasn't that big, but I was getting a little nervous. She lubed it up and started to slowing push it into me. "Come on baby, open for Mama." I tried to relax again, and it seemed to slip right in. I knew that made her happy. She spent some time slipping it in and out of me. I think it might have been as long as ten minutes, and it was easily moving in and out.

She cracked me on the ass again as she took the dildo out. Then she stood up. I looked at her obviously confused. "That's enough for now Tiger. You know you can handle this. Even if I go to a bigger dildo, you've seen how easy it is to do. Just relax, and it will be easy. After all, it is supposed to be your first anal experience. We can't have you looking like a pro your first time."

I headed off to the kitchen, still naked. She called at me from upstairs, "Don't you dare eat anything! I don't want to have to clean you out again."

Well, that was depressing, because I was hungry, but I would go hungry to avoid doing that again. There didn't seem to be any beer in the frig, so I grabbed a bottle of wine and poured myself a glass. It was early still, but I thought I'd feel better later on if I started to become Molly now. So I downed that first glass and went and put my thong on.

My thong is kind of special. It's got a pocket in front that hides my masculine part and keeps it tucked away underneath. As long as we're just a little bit careful with the cameras, you can't see my cock and you would think that my pussy is under the thong. Anyways, it felt more natural walking around naked without having my cock sticking out in front of me. That probably goes to show how far gone I really am.

I must have fallen asleep on the couch, because it was about 6:00 when I became aware of the time. I still had two hours to get ready, so we were OK, but I felt rushed. I got upstairs and poked my head into Aunt Janey's bedroom / studio. Her bed had been moved a bit so the corner was no longer facing the cameras, but the foot of the bed was. I looked at Aunt Janey and she understood my look.

"Hey baby, a couple of adjustments as you can see. We're going to have you right here at the foot of the bed." She patted the foot of the bed, like I needed to understand her better. That's when I realized she might be trying to distract me from the headboard. There were ropes tied to the headboard.

"Um ..."

"Sweetie, it's your first time." She was using that 100% sugar voice, so I was expecting trouble. "Look, you jumped around a lot when we were practicing. If you do that on film, your big reveal is going to happen tonight."

She looked down and saw I was wearing the thong. "You can't wear that tonight. It would get in the way, block your ass. Besides, they are going to be staring at your ass. If your tong covered head pops into view, it won't look good. I'm actually going to tuck your little gentleman there up under your corset. By tying you down, it explains why you're not moving around. If you move, they'll know, so this way it makes more sense."

As usual, she was being all friendly and coaxing, but her temper flared up there too. "Hey, I'm the director, and this is what I want."

"OK, Aunt Janey", is all I said. She normally didn't snap at me, so this whole thing must have had her under some serious pressure. I hadn't realized it was doing that to her. It was after all her job, and she was clearly working hard to get the right pay day.

She came over and kissed me on the cheek. As she pulled back she casually fondled my package in the thong, but my reaction was anything but casual. In a very soft voice, she said, "Go get changed into things sweetheart." Being the smart nephew, I went off and got changed.

Twenty minutes to go, and I was all ready. My make-up and wig were on perfectly. I had the bodice on, but nothing else. Aunt Janey wrapped an elastic bandage around my cock and balls and tucked them up inside the bodice. Then she got me positioned on the bed and started checking camera angles. I think we were both starting to get worried about time, because she kept trying to adjust, until she said, "Fuck it, that will have to do!" That's when she started tying me down to the bed.

I thought the bondage stuff was just going to be for show, but she didn't want me moving at all, so she was tying me down securely. The pressure of the ropes was smashing me into the bed. I couldn't move more than an inch or so, tops.

Right at 8:00, she flipped on the cameras and started talking to them. I think she was giving everyone a chance to tune in a little late, because she was talking for a while. I kind of stopped listening, because she was really playing to the guys in the crowd. She was even answering a couple of questions that came across the chat portion of the show site. I think it was more about the number of viewers than the time but she eventually decided it was time to actually start.

She was naked, as she had been all day, but I couldn't see her behind me like she was. I felt her sit on the bed, and I knew those big beautiful tits of her were front and center on screens across America, maybe the world.

"You know why we're here tonight, right? This is a big occasion for our little girl Molly here. I'm going to pop her anal cherry tonight - live, just for you. As we were trying to get ready for tonight, she started to get a little nervous about the whole thing. I was a little nervous that she was going to chicken out, so you can see I've taken matters into my own hands. No way she's getting out of this!

"You know, I don't have a lot of experience with tying folks up, so let's take a look, OK?" I felt her get up off the bed. I didn't realize until she came around by me that she had a handheld camera. She was filming me, well, me and the ropes holding me in place. I think she wanted to prove both that she had securely tied me and that it was in fact me. She waved at me as she came around, but clearly, I wasn't positioned to wave back.

She went back to the foot of the bed and must have been filming the ropes, because she sort of tugged on the ropes holding my legs. She wasn't talking, which was unusual for her. She almost always kept up a running dialog while the cameras were running.

I felt her sit on the bed, but more to my side than directly between my legs like when she started the show. I think she was reading the scrolling comments from the fans because she said a couple of things that didn't really seem right. Something like, "Yep, thanks, I saw that too."

There was something in her voice. I was getting to know her pretty well, and this was like her almost cumming voice, though normally then she was panting. She started running her hand over my ass. I was pretty excited, but I think she was way more excited than I was.

"So this is Molly's ass. This is what I'm going to fuck tonight. I have to tell ya fellas, I am really looking forward to this. Way more than I expected." I was right. She was really turned on right now. Part of me was also turned on by that, because she is one sexy woman, but I also felt nervous. What was going to happen to me if she got carried away?

That's when she smacked me, just like the other night. It stung, no question about it, but it's not like I was actually hurt. I imagined that it too was going to raise a red mark on my butt. Then she spanked me again on the other side. She was right, the ropes kept me from moving, because both times I tried to jump a little, involuntarily, but I didn't go anywhere at all. When she hit me the third time is when I heard her giggle. Yeah, I was in trouble.

I gritted my teeth, and she started spanking me faster. It's not that I was never spanked as a kid; my mother believed in that. But this was different. First of all, I think Aunt Janey was using her full strength. And she was enjoying it. There could be no question at this time. Whatever else was between us, my aunt was becoming highly turned on by spanking my bare ass.

I don't think she had said much while she was spanking me, but as she finished, she leaned off the bed and reached for something. Again I couldn't see, but she started talking to the cameras again. "So now that I've turned Molly's cute little ass all red, I wanted to show how I feel about Molly." Something cool was being rubbed on my butt. It took a few seconds, but I realized she was using lipstick to draw on my ass. Not write, draw, and I think it was a big heart. Yep, she had used red lipstick to draw a heart on my ass, and the spanking had turned my entire ass red to fill in the color of the heart.

I could imagine what their screens looked like - My ass centered and probably zoomed in. Red from the spankings and now outlined in lipstick. That was the image left as Aunt Janey stepped into the harness that would hold her strap on. When she came back into the shot, she was modeling the strap on. She did a few poses in front of the cameras and then sat down again.

"Now, we all know what Molly is, an anal virgin. So instead of just ripping into her, we're going to open her up a little bit." I felt her fingers with the cool gel on them. It felt a lot cooler now that my ass felt fiery hot. Like before, she started to rub the gel on my anus. She wasn't being as slow and steady as before. I think it was how turned on she was, but she seemed to be rushing things.

She inserted a finger and started to get the gel around inside me. I was calming myself and trying to get ready for the first small vibrator, but then she stuck a second finger in. It sort of took me off guard, but it didn't feel bad. Honestly I was really worried to admit it, but the spanking had seemed to make my ass feel more alive. I felt every touch, every sensation. Sure the spankings had hurt, but even though I should probably be hurting right now, I really felt like my ass was more sensitive and attuned. That's what was going through my mind, even if I'm using the words wrong. It's not like I was thinking clearly.

I can't be sure, because she was moving her fingers around a lot, but I think she may have slipped a third finger in. Then she pulled her hand away and I am pretty sure she started to lube up the dildo in her strap on. I actually calmed while I was waiting for the dildo. I had done this before, and I liked it. Clearly, Aunt Janey was liking it too.

I felt the head of the dildo touch my anus. Aunt Janey was talking to the cameras again. "Are you ready boys? Is this what you want to see me do to this little girl? Wow, you viewers are just nasty! You want me to do what? You want to get on with it? You think I'm stalling? Hey, I'm a professional - I'm checking to make sure that you guys have the best possible camera angles. OK, I think we're good. It's time to get this done."

She started to ease the dildo forward and into my ass. I sensed it almost immediately. This wasn't the dildo she had showed me earlier. Whatever this was, it was a lot bigger. I think I squeaked, and I know I was trying to scramble away, but Aunt Janey had tied me down way too well.

At this point it was inevitable, Aunt Janey began to put the pressure behind that fake cock and it started to spread my sphincter. Nothing I was going to do was going to stop her; I just had to try and relax so it wouldn't hurt as much. Thank God she had lubed it up. Well, I guess I was happy. The lube was letting it slip all the way in. Without lube it might not go in, but I doubt Aunt Janey was going to let that happen on camera.