Just Look at Me Now Ch. 04

Let's see... where was I at the end of chapter three? Oh yes: seated on a footrest wearing lingerie and my pink collar, with my eyes adjusting to the bright light now that my blindfold had been removed—and adjusting to the sight of Jude's strap-on in front of my face.

"Have you ever given another guy head?" Jude asked.

"No, never!"

"How about getting a blow job from another guy?"

"Never."

"Not even once at some frat party or something? Or how about trading hand jobs with other guys?"

"No, I haven't done any of that," I said. "I'm not gay, you know," I added stupidly.

"Well, something tells me you aren't exactly straight," said Becky. "You know, considering your panties and makeup and all." Good point.

"You have gotten bj's from women, though, right?" asked Jude. Indeed I had. "So, I want you to suck my cock with all the skill and enthusiasm of the best job you've ever received. This is a first for me too—not to have my strap-on serviced, as Becky can tell you, but the first time to have it done by a sissy.

"Look at Nicole's panties," said Becky. "She is eager to please you!" My erection wasn't lying, but it wasn't telling the whole truth and nothing but the truth. I wanted this—for the new sensation, for the humiliation, and to give Jude an erotic thrill—but I was afraid as well. What is left of one's masculinity when one sucks cock on demand?

"Pull your panties down for a moment, Nikki, so we can see your clit," instructed Jude. I did so, and she put her hand on my cock and gave it a quick squeeze. "Well, my dear, this is the very essence of tumescence! Your clit is even harder than my cock, though of course it's quite a bit smaller. You may tuck it back in now."

"One other thing to keep in mind: if you do a good job with this strap-on I may not make you suck the big one today. Beck, are you ready to take pics?"

The cock I was about to suck looked plenty big—significantly stouter than my own and plenty long as well. I did not want to even think about "the big one." Beck unlocked my camera and shot a test photo. "All set," she said.

"OK, Nicole, begin."

Jude inched forward and I leaned in to give the tip of her strap-on a gentle kiss. I explored the whole length of the dildo with my lips and tongue, beginning with the head and working my way down to Jude's leather harness. Moving back up, I licked the glans and the area just below, which for me is the most sensitive and pleasure-laden bit. And then the moment of truth, as I took the entire glans in my mouth and began rhythmically sucking. My camera phone was clicking away nonstop... just look at me now!

Jude rocked in gentle rhythm with me, and in the first few minutes of my cock sucking she talked to me occasionally. She said that her harness had been designed by women to position the base of the dildo right on her clit. She said I was becoming one of her favorite sex toys, and that any guy would be lucky to have his cock sucked so lovingly.

While my mouth was thus engaged, my ears played a trick on me. Becky said something I didn't understand. It sounded to me like "You know, Jude, if Nicole has never sucked cock before, it follows that she's never been Skoal-fucked."

"Skoal-fucked?" Something with tobacco?? That made no sense. Maybe it was "school-fucked," as in fucked at school or like a school girl? That didn't make a lot of sense either, but with my mouth full of dildo I couldn't inquire.

"Great idea, Beck!" said Jude. "Do me a favor and do a quick tie of her hands." I had a minute or two to consider what school-fucking might be as Becky retrieved a suitable length of rope. Until now I'd had my hands to steady myself, but now she placed them behind my back and bound them loosely together at the wrists. As she did so, Jude held my shoulders to help me keep my balance.

Once I was securely bound, Jude took my head in both hands and began to thrust her strap-on more vigorously into my mouth. She rocked my head forward and back, taking complete control of the rhythm and forcefulness of her penetrations. The tip of her dildo slammed into the roof of my mouth and pushed back to my throat. And now I understood what Becky had said: I was being skull-fucked.

After a long series of deep thrusts that put me on the edge of gagging and made it hard to breathe, Becky pushed the full length of her shaft into me and held it there, making very rapid short thrusts. Instead of using her fingers or a vibrator to stimulate her clit, she was using my head and the dildo that was crammed into my mouth. I made a couple of instinctive attempts to pull back my head—to free my mouth or at least make the penetration less deep—but with my hands tied I had no leverage, and Jude just kept fucking my skull. As she grew more excited she told me to imagine her squirting a load of cum into my mouth, to imagine the taste and warmth as I swallowed her semen. Moments later she began to orgasm. As she came she squeezed my head hard against her for several seconds, then delivered five or six long thrusts of the dildo before pulling out.

I caught my breath, assessed the condition of my mouth (teeth intact, muscles exhausted, throat mildly irritated), and prayed that Jude would not tell me to start all over again. My prayers were answered when Jude suggested a break for showers and what she called a William Burroughs lunch—that is, a Naked Lunch. My collar was unlocked and removed, we took turns showering (guess who went last), and then it was lunch for them and naked for me. I made their sandwiches, poured their lemonade, stood naked and silent as they ate, and cleaned up the plates and crumbs.

As you know, the next item on the agenda was my ass. Becky instructed me to follow her to the living room and to remove and fold the faux-Navaho blanket which covered a low table in a corner. This was a rather ugly table that had always struck me as cluttering the room with no purpose other than being a magnet for jackets and mail and catalogs. The table was even less impressive without the blanket—a simple rectangle whose top consisted of three sections covered in black "leatherette," or to use the Italian term, plastic. Becky had me carry the table to the center of the room, not an easy task given its heavy steel legs.

This all made sense to me only when Becky popped the middle section up and secured it in its raised position with two bolts. In this configuration—like a miniature picnic table and benches—its true nature was clear: it was a spanking/buggery bench.

Following Becky's instructions, I positioned my knees on the two sides and my torso on the raised center section, with my genitals hanging just off the end. The bench was long enough that I could rest my chin at the other end or let my head hang loose. Becky then bound my hands in an appropriately prayerful position and anchored them to an O-ring; I could move them but was not going anywhere. Back at the other end of the bench she looped something around my balls; I couldn't see it, but she informed me that it was a pink hair scrunchie, and that she would now spank me just enough that my cheeks matched its color.

The spanking was not as robust as a couple of the over-the-knee spankings I'd had before, but I felt especially vulnerable on the bench, and I knew this was just the warm-up, not the colonization of my anus.

Once my cheeks had been sufficiently colored and photographed, Becky came around toward my head. I could see her feet in the black boots I had cleaned that morning, and now she had me watch her put on a pair of tight black latex-free medical gloves. She assured me that she would use a top-quality lube and that she and Jude had been rereading "Anal Pleasure and Health" in preparation for my training.

"Your instructions are simple," Becky said. "Let me know if anything hurts, and just keep breathing." I few moments later I felt the cool lube on my ass as Becky sought and found my hole. My anal cherry was about to be popped, and Jude put my camera phone into action.

I had always thought of my anus and rectum as one-way streets despite its lack of "Do Not Enter" signage, not to mention the colonoscopy looming on the far horizon. The sensation of something going in, now familiar, was then completely new. I felt the combination of humiliation and nervous anticipation that I find so arousing. I felt the tip of Becky's finger enter me, and then the slightly larger joint. "What a tight little pussy you have!" she said as she moved that joint back and forth over the tightest bit of my anus. She removed her finger entirely, added more lube, and entered me again. I was being fucked.

I relaxed as best I could and concentrated on my breathing as her penetrations gradually grew deeper and her full finger probed my ass. I had expected the emotional intensity of offering up my anus as a plaything, but I was astounded by the physical sensation as Becky stimulated my prostate. I was discovering a new erotic zone, connected to my cock and involving the entire pelvic region.

My sense of time was no doubt distorted, but I probably spent about twenty minutes learning that Becky—and no doubt Jude in the future—could control the pace, intensity, and duration of my anal submission. She occasionally withdrew her finger entirely, suggesting we might be done, but after a pause—sometimes a few seconds, but up to a couple of minutes—she would enter me again without warning. Jude continued to take pictures and to give me some spanks and pinches "just to keep the color in your cheeks."

Eventually, after a series of unusually robust thrusts, Becky let her finger rest quietly deep inside me and Jude announced that my next homework assignments would be explained while I was still bound to the spanking bench. I was resting my chin on the end of the bench and saw Jude's feet as she approached and patted the back of my head. "This will be your most challenging shopping task so far," she said.

Then I saw Becky's boots right below my head! That couldn't be—her finger was still up my ass. But her finger couldn't possibly be up my ass, nor could Jude's, so either my ass was unoccupied after all, or, or... I'd been given a butt plug.

Moments later it became exactly clear what plug was now resting inside me. Jude showed me a plastic tray with indentations to hold four plugs of increasing size; the three largest plugs were resting there in place, but there was an empty hollow for the small plug Becky had snuck into me.

"This is obviously a training set," said Jude. "Becky has been kind enough to let you borrow her beginner plug, and like she did you will gradually proceed to the bigger ones." The plugs were solid black, and the range from small to large was dramatic. It was hard to imagine ever taking the biggest one, but I knew that was a goal.

Jude named the specific sex toy store where I was to do my assigned shopping—a very respectable erotic boutique in Palo Alto's chic downtown. "The first items on your list are a bottle of lube and this set of butt plugs. Both are currently in stock, and we will give you the SKU numbers so you get exactly what we have picked for you. Also, you must make clear that the plugs are for you, not a partner. You will make an audio or audio/video recording to prove that you are following these rules."

Jude then held a sealed envelope where I could see it. "Your instructions are here," she said, "and—this is very important—we have also given you SKU numbers for two additional surprise purchases: you won't know what they are until you shop. Again you must make it clear that these items are for your personal use, and you must prove it with a recording. Finally, you must ask a specific embarrassing question about each of the surprise items. We have written these down with the SKU numbers. You can peek at the questions ahead of shopping or not—the anticipation of shopping will be excruciating either way."

Ten minutes later, having successfully peed with both women watching, the scrunchie still around my balls, and the training plug still up my ass, I was driving home, eager to give myself my first plugged orgasm and to check the dozens of photos Becky and Jude had taken.

I'll tell you about my embarrassing shopping in the next chapter, but I can share the two questions I would have to ask. For the first item, it was "May I return this if it's too big?" and for the second, "Can this link to two phones at the same time?"

Stay safe, wherever you are, and keep an eye out for chapter five in a few weeks—the Halloween chapter at last.