Chapter 12

Despite the cold weather, my daughter-in-law Ann dressed in the shortest skirt I’d ever seen her in. The rest of her was bundled up for a New England winter, but she was all legs – and damn good-looking ones at that. She was wearing ‘come fuck me’ heels, too, and looked a little tarty the way she’d applied her makeup. I learned that she was commando and planned on flashing guys wherever we ate dinner. We all had a laugh, but she pulled the front of her short skirt up and proved her point.

Jasmine gave Ryan a knock-you-socks-off kiss in the lobby as others in the reception area watched. We went to dinner at a nearby Tex-Mex restaurant and caught up. I learned that Jasmine had had several long phone calls with Ann coaching her in how to be a porn star actress and also helping her get over her nervousness about being in a movie that millions of guys would jerk off to.

I’d never seen Ann so hyped up. She was manic in every sense of the word and told us that her kids had even noticed and commented about how happy mommy was.

I commented, “You know some day your kids may discover that you’ve done some porn videos; what do you think they’ll think?”

Ann launched into a diatribe about how I was trying to talk her out of appearing, but after several tries I got to explain that I wasn’t. The telling turn in our brief argument was when I leaned over and told her I wanted to fuck her while being filmed so I could always remember having made love to my daughter-in-law.

Ann thought a bit and replied more thoughtfully, but still in rapid way, “Well, I guess I’d hope they thought that their mother was a nonconformist, and did things that most others wouldn’t do, and that she was sexy, hot, and a great fuck.”

I teased, “Maybe they’d want to have sex with you?”

Ann looked at me as though I’d said something very profound, “Oh, God, do you think they would? I wonder if I’d be up for that. That’d be really different.”

Ryan stepped in, “You don’t have to decide for many years, honey. Just relax. Focus on the next couple of days and not on something that might happen in fifteen or twenty years or more.”

Ann visibly relaxed and then went at Jasmine with unbridled enthusiasm, asking her to describe what she felt like the first time she’d done a porn video. From the questions and her attention I gathered they hadn’t had this discussion in all of their phone calls. I learned later that the calls were more instructional, for instance, don’t look at the camera unless told to do so; keep you leg nearest the camera in a low position so you don’t block the view of the cock in your pussy; be sure the camera can see your tits, rub your clit part of the time you’re being fucked; look at the guy fucking you a lot; you can close your eyes but look like the fuck your getting is pure ecstasy, don’t hold back on your own responses; and so on.

Jasmine then made a telltale statement that stopped Ann in her tracks. “That first time for me was also the first time I’d had a cock up my ass. I’d never done anal before.”

Ann paled, “Anal?”

Jasmine said, “Yeah. I told you to prepare to get fucked in all your holes.”

Ann said in a timid tone, “I didn’t think that hole counted.”

Jasmine asked, “So, you haven’t done anything to prepare?”

“No.”

“We’ll stop at a drug store on the way back to the hotel. There are a couple of things that’ll make it easier for you, and I can lend you one of my butt plugs.”

“Butt plugs?” Ann whispered. “What are they?”

Jasmine rolled her eyes, “Yeah. You put it up your butt after you’ve given yourself an enema and it’ll help stretch out your muscles and prepare you for anal sex. It can be a lot of fun and stimulate areas you never knew about; you might get lots of orgasms that way.”

“Oh, dear.”

Jasmine went on to explain in more detail about what would happen at each hole. Her expectation from having worked with Jerry is that he made complete use of the female ‘models’ in his films, especially the newbies like Ann. Some of the discussion was for shock value and I had to keep from laughing at how the worldly porn star was subtly teasing my mostly naïve daughter-in-law.

We did make a stop on the way back to the hotel, and then we congregated in Ryan and Ann’s room with a couple of bottles of wine. Jasmine took Ann into the bathroom and they were busy for a while. When they came out Ann was walking funny. She turned around and lifted her little skirt. She was still commando, and also displaying the recovery end of a butt plug.

Jasmine came and said to me, “When you fuck her later pull that out and use two or three of your fingers back there. We reamed her out so she’s pretty clean. We’ll do it again in the morning.”

Ryan and Ann did swap partners with Jasmine and me that night. Ryan again looked like he’d died and gone to heaven to have another shot at Jasmine. We were close by on the other bed in the room, and Jasmine put on a full court press to drive him crazy, especially with her dirty talk. I did as Jasmine had suggested. We discovered in the process that Ann probably liked anal sex. She had three intense orgasms as I finger fucked her ass and toyed with her clit.

We met Jerry for breakfast in the hotel restaurant. He’d gotten in late the night before and told us he’d already done some of the set-up in his suite in order to do the filming. He was exceptionally cordial, especially with Ann. His greeting with Jasmine reflected their long-standing friendship that included having fucked each other silly more times than they could count, usually while being filmed.

After the pleasantries of greeting for the first time, he had Ann tell him about her sexual experiences and preferences. She admitted to being pretty ‘vanilla’ and he assured her that was not an issue. He flashed a lecherous grin at her and said, “Everybody has to start somewhere.”

Jerry outlined the next two days, splitting the day into roughly ninety-minute segments with two that morning and three in the afternoon. If Ann was up to it, he thought they might fit in an evening session that night or the next. He was making this a longer than usual casting video.

Jerry told her, “We’re going to get you on film in a number of ways. It’s not all going to be video. I want several hundred quality still photos of you. Some we’ll take as we film, probably as a segue to a rest break. The first session this morning will be me filming you for an interview and then you masturbating in several different ways.”

Jerry went on outlining the rest of the day, the evening session if we were up for it, and then the next day. I was surprised to discover that Jerry included all of us in the videography. Whenever one of us was not ‘in the saddle’ he wanted that person or persons to have a camera in their hands filming the action. The next day he also wanted all of us to engage in sex with Ann in some way, sometimes two or all of us at the same time. Ann would be the focus.

After breakfast we all went up to Jerry’s suite. The room had two bedrooms and a living room with a large screen television and other amenities. He’d set up various light panels in the living room and one bedroom. He cranked up the air conditioning and turned on the panels.

Jerry started with Ann sitting provocatively in the middle of the king-size bed fully clothed. He gave her the name Ann Sweet, and told her in all future filming this would be her stage name. He also gave her some prompts and explained about his short interview as he filmed her with clothes on. He also wanted her to look sexy and do sexy things. Ann was ahead of him on dressing sexy. She was still manic about doing the videos and smiled a lot despite being unsure of herself.

Jerry hushed the rest of us, made us stand at the door to the bedroom, and then started filming. He talked to Ann Sweet from behind the camera. His questions were suggestive and he’d told her it would be great if she created a sexy and horny persona for her ‘on screen’ character that could follow her.

The early round of questions were demographic: name (Ann Sweet), where are you from (Rural northeast), how old (thirty-one), marital status (married but plays around with and without husband’s knowledge), sexual preferences (men, but wouldn’t turn down a chance to eat good pussy), and so on?

The next round of questions dealt with the filming: have you every done a porn film before (no), why are you here (want to put myself out there for people to see – especially guys who might find me sexy enough to jerk-off to), anything else (want to get fucked by an expert; heard you had a great dick that would touch places my husband can’t get to; have my pussy eaten for hours; and get covered in cum)? There were more questions that Ann responded to over fifteen minutes.

Jerry then suggested that Ann remove her clothes so he could show people watching the video what she ‘really’ looked like. Ann slowly and carefully disrobed, barring her breasts first, and then shedding her skirt and thong. He suggested that she relax and see whether she could make herself cum like she might if she were home alone and really horny.

Ann layback on a couple of pillows, shut her eyes, and went to town with both hands on her pussy. The fingers of one hand started to massage her clit and mons, as those of the other hand started to penetrate her moist vagina with two or three fingers at a time.

Ryan and I were entranced watching her. After Jasmine came back to stand with us after a long camera shot of Ann’s pussy activity, I started to toy with her breasts as I pressed against her ass with my hard-on. I motioned for Ryan to get involved, and he joined me in pawing Jasmine’s sexy body.

After about ten minutes Ann orgasmed. By then her pussy had gushed her fluids all over her hands and the bed. She collapsed and squirmed around on the bed for a minute as her orgasm plundered her body. Jerry ended with a close up shot of her pussy before he stopped the camera.

Jerry praised Ann, assuring her that she’d done a fabulous job for her future audience. Many men loved watching girls masturbate as they did the same. He confirmed to her that he had some great footage.

Ann remained naked as Jerry uploaded his two cameras to his very powerful laptop, checked the upload, and then backed things up to two separate thumb drives. He also got the clip that Jasmine had taken.

The next filming segment was Ann giving Jerry a blowjob. This was still in the skill range of Ann’s normal sexual activity. Somehow, Jerry lasted an hour as Ann worked him up, down, sideways, in, and out of her mouth, occasionally tit-fucked him, and then got splattered over her entire face with his semen.

Jerry announced a break for lunch. Ann complained that her entire jaw was so sore, she wasn’t sure she could even eat. “I’ve never had to suck something for so long. I hurt.”

Jasmine got her some ibuprofen and assured her that she’d had the same problem multiple times. Jerry was sympathetic and explained that in future shootings, at least where he was concerned, she should tell him when she was feeling poorly about something that was happening. He showed her a hand signal she could use and he promised to change the activity and-or just give her a rest.

The five of us went to lunch in the hotel restaurant after Jerry and Ann dressed. Ann, of course, washed her face and got the cum out of her hair with Jasmine’s help. Jerry gave Ann more instructions to choreograph the afternoon’s segments. He emphasized that he wanted her to be spontaneous in how she responded to him, but keep in mind the two cameras that would be filming them.

Ann got vaginally fucked right after lunch. She seemed ecstatic about the prospect and then the reality. She often smiled in satisfaction, and spoke encouraging words to Jerry who was pumping his long cock in to her pussy. I thought she’d had several more orgasms.

Jasmine and I manned two cameras so Jerry could focus on the scene and his partner. She’d given me enough lessons and we’d critiqued some porn videos as though we were cameramen, so that I felt I had a good chance of turning over something credible to Jerry. What made things especially appealing is that Jasmine removed her top and bra. My son Ryan was the voyeur watching his wife get fucked in some carefully orchestrated positions.

Occasionally, Jerry would stop in mid ‘pump’ and ask Jasmine or me to assume a particular camera angle. We’d been told to not stop the cameras until he specifically told us to. He’d edit away all of the clunky transitions.

I had a perpetual hard-on as I watched Jerry fuck Ann. Jasmine’s partial nudity wasn’t helping any either. Moreover, I knew that tomorrow not only would she be camera, but she’d also be getting fucked by each of us.

Jerry broke after an hour, backed up all the camera footage onto the laptop and memory sticks, and then started again except segueing into different positions that then got filmed. At the end of the afternoon, Jerry jettisoned a huge load of cum into Ann’s pussy. They’d been fucking most of the afternoon. Ann had cum a couple of times as Jerry rubbed her clit with his fingers, but he managed to hold off until he was ready.

Jasmine and I filmed the epic climax of their afternoon fuck including the cum leaking from Ann’s pink pussy. I noted that Ryan had masturbated into tissues at least twice as he watched Ann get planked. Jerry injected some liquid into Ann’s pussy and then took more close-up shots as she oozed what was supposedly his cum from her pussy. In reality, it was some cultured buttermilk that had been thickened with yoghurt to look just like a massive load of cum. Ann giggled at being impregnated with the mixture and then helped by squeezing the thick fluid from inside her as the cameras captured the action.

Jerry finally said, “Cut! All cameras off.” Jasmine and I stopped. We all applauded our new porn star Ann Sweet. Ryan came and kissed his hot wife, adding his support and encouragement to everyone else’s.

Jerry saved and backed up the afternoon’s work as before, and then on his laptop computer jumped into the middle of one of the afternoon video clips where Ann had been riding Jerry in a reverse cowgirl position. She was spectacular, and as good as Jasmine had been in some of her films.

Jasmine teased her, “Oh, shit. Now, I’ve got my boyfriend’s daughter-in-law competing with me as the lead porn queen on the Internet.” Everyone did agree that Ann was hot, sexy, and appropriately lewd, crude, and obscene in a way that would inspire millions of male orgasms around the world. I remained hard, and called that to her attention as one additional indication of how hot she was.

Jerry took us all to dinner at a nice upscale restaurant in Cambridge. It was nine o’clock by the time we got back to the hotel. We all looked at him wondering whether he wanted to film anything else, and he just waved us off. He said, “Come on up to the suite. We can just sit around and drink – or fuck – or whatever inspires us.” We did all of the above.