Explanation to the Sororitybyescriterra©
"I think we all know what's going to happen here this evening," said the woman who had been teasing me online for two months. That this night was the first time I had met her in person punctuated my obsession with experiencing what I knew beyond all doubt would be the most exciting sexual experience of my life.
"Ladies, this is the gentleman I was telling you about." She looked at me and smiled. "We will assume you will be a gentleman this evening, Scott." I was ready to agree to anything. Had been for weeks, ever since seeing the picture Karelle Matthews had sent me. Though tonight she was dressed simply, even conservatively, her attire could not hide the form that I knew matched the picture.
Her finely knit pullover top and matching slacks clung to her curves this evening. They were the same curves so readily apparent in the picture she had sent. Tonight, though, in place of the corset and stockings she wore in the picture, she revealed little other than a lovely silhouette topped by a beautiful face framed by hair that was a cross between red and chestnut brown.
And right now, she certainly wasn't wearing the strap‑on dildo that was part of her outfit in the picture.
Turning to the assembled group before her, Karelle said, "Scott has agreed to provide you all some fascinating information, haven't you, Scott?"
There were seven young women in the room. It was the large living room type area of a suite in a swanky hotel. I didn't even remember the name of the hotel, so entranced was I with the woman in charge of the proceedings. She had met me at the airport baggage claim area of the airport earlier that evening. (This in spite of the fact that all I had with me was my small business satchel. She said there wouldn't be any need to bring a change of clothes.) She whispered in my ear as we rode in the taxi to this place:
"You're very good to do as I directed, Scott," she cooed. "Are you ready to experience your darkest, most exciting desire?" Her perfume was light, airy, yet unmistakable. I promised myself that I would visit a department store as soon as I returned home and sniff my way through the women's fragrances until I found it. I was desperate to remember everything about tonight.
You can see that I was mightily distracted during the taxi ride from the airport to the hotel. Her sexy teasing about the desire I'd shared with her in such detail over the Internet meant two things: I could focus on nothing except her, her words, her smell, the gentle way she laid a hand on my shoulder as she whispered nasty things to me. And I squirmed constantly in the seat to try to find a position that would allow some freedom in my trousers to accommodate the erection she was skillfully creating with only the sound of her voice.
"You did as I told you, correct?"
I mumbled assent.
"Ooh, this will be such a treat for you, Scott."
And so it went the entire drive from airport to hotel. I can not tell you how long we were in the cab, whether it was a mile or twenty miles. And the trip across the lobby and into the elevator was torture. (You try being unobtrusive with seven inches of stiff dick trapped underneath the crotch of your pants in an awkward position with no good way to adjust in mid‑stride.)
The elevator door closed behind us. She laid a hand firmly on my backside, grabbing a cheek and squeezing it. "So far so good, my young stud. Your description of yourself seems to have been accurate." She drew me close to her. "A nice, taut ass is very important to my pleasure." Leaning next to my ear, she whispered, "It's going to be exciting watching my strap‑on dildo slide between your firm asscheeks."
I gasped in response.
Then she placed one hand on the back of my head, slid the other down to my crotch, and pulled my face to hers. She devoured me in a deep tongue kiss, pressing her mouth on mine and ravaging me. Stopping only for an instant to say, "Give me your tongue," she continued kissing me. Owning me. My tongue became a suck toy for her.
The elevator doors slid open. She relinquished her control of my face and mouth. My dick remained stiff.
Karelle guided me to a door several yards down the hall from the elevator. She opened the door and motioned me in. With my satchel in hand, I stepped through the doorway, hearing sounds of female conversation a few feet inside.
And so here I was.
"The sorority has promised you an enjoyable education tonight," said Karelle to the group. I nervously toed the carpet, not yet able to look up into the faces of the coeds seated on the couch and chairs in the room. I felt a flush rising up my neck. It seemed to be getting much warmer.
"Mr. Gooding has been directed to share with you the reasons he likes for a woman to fuck him with a strap‑on dildo."
The pit of my stomach clenched at those words. I knew she would say them. She told me she would as part of her description of the events she would orchestrate for this evening.
And therein lies one of the many reasons that being taken by a woman wearing a strap‑on dildo is so exciting: When she talks about what's going to happen, about what she's going to do---and to make me do---that just amps up the crazy, intense sexiness of the entire scenario.
The anticipation is such a big part of the pleasure. Maybe even more pleasurable is thinking about what she'll say before she gets down to business. Yeah, maybe that's a huge part of the turn‑on. In the days and hours before an encounter when I think of what she'll do and say to tortuously draw out the anticipation for her own pleasure until I'm begging to be fucked, I will have my fist wrapped around my cock, stroking.
When I spurt during these masturbatory episodes, it's often brought on by imagined words whispered in my ear about how much she'll enjoy taking me. Her descriptions of how she likes to see me opened for her pleasure, twitching in anticipation of surrender to her control, are words that create sexual tension in me beyond description. Hearing these things, knowing she will do them and I will submit---this is a big part of the turn‑on for me.
I would be forced to tell the coeds in the room all of this.
"Come. Sit." She led me by the elbow to a straight‑backed, padded chair with arms. It was positioned at the head of a make‑shift semi‑circle of chairs and a couch that had been arranged in this space. Taking the remaining empty chair---the one next to mine---she looked at me thoughtfully for several seconds. The girls quieted.
"So, ladies . . . what do you want to know?" Karelle smiled evilly at me.
There were two black coeds in the group. One of them (short and voluptuous) immediately spoke up: "Is this really true? Are you really here to tell us that you enjoy getting screwed in the ass by women wearing strap‑ons?"
The rest of the girls laughed at that, though I caught a nervous cough or two.
Karelle waited expectantly through several seconds of silence as I tried to gather the courage to look at these young women and begin my descriptions.
I looked up, wringing my hands miserably in my lap. How, in the many iterations that I'd played this out in my head as I stroked my cock, could I have thought this would be exciting?
"Look at Celia and give her your answer, Scott," said Karelle.
That reminded me why I was excited at the thought of this. Karelle was going to fuck me tonight.
I swallowed. "Yes." My answer was barely audible. Catching a reprimanding look from Karelle, I cleared my throat. "Yes. I really do like being screwed in the ass by a woman wearing a strap‑on."
That seemed to break the ice. A simple question from a blonde to my left followed: "Why? Are you gay?"
Oh, I knew that was coming. So did Karelle.
"Kristi, ladies, you must all disabuse yourselves of the notion that 100% of men who enjoy being taken by a woman are gay. In fact, most of them are not." She looked at me, stood up, and took the one step necessary to stand at my side. "Scott likes it up the ass only occasionally, and the rest of the time he enjoys sex in the ways you would guess." Karelle laid a hand on my shoulder. "Isn't that right, Scott?"
Before I could answer, a brunette seated on the couch blurted out, "So you like licking pussy, too?"
"Jenna!" exclaimed another, taller brunette. "Don't be so crass!"
Karelle, ever the knowledgeable big sister, quickly commandeered the conversation. "It's okay, Talia. Things will go much more easily if we don't stand on ceremony or euphemisms. Scott is going to have be quite descriptive for us this evening, so let's all agree that, while ladies don't talk this way in public, when toying with a man before taking him---as we are doing with Scott tonight---part of the sexiness is giving ourselves the freedom to use language designed to arouse the male." She leaned into my ear while looking at the girls in front of us and said, "Now, Scott, do you enjoy licking pussy?"
This was not a difficult test. "Very much."
"Do you do that before they fuck you, or after?" asked the other blonde in the group.
"There's no definite order. It's the same as how it happens when you screw without using a strap‑on. Sometimes you do things one way. Sometimes you do it a different way." I was starting to relax.
"Whatever put the idea of asking a woman to fuck you with a strap‑on into your head?" asked the coed who looked to be Asian.
"Well, I didn't ask the first time it happened. She teased me all night, finally started giving me a blowjob, and then she began licking my balls."
"Eeuww." In unison, most of the girls indicated that they would never do such a thing.
"Continue," said Karelle, returning to her seat.
"So she licked my balls between bouts of sucking on my cock, and before I knew it, she was circling a finger coated with some lotion around my . . ." I hesitated, knowing that I was about to start describing things that would make me really horny in front of these young women. Already, my cock was starting to rise to whatever amount it could, trapped as it was in my pants as I sat on the hot seat in front of these college coeds.
Karelle used the pause to tease me. "He's probably embarrassed to talk about how the woman fingered his asshole." She smirked. The girls were wide‑eyed. Silent. Waiting. I felt the unmistakable blush of shame creep up my neck.
"Is that what she did, Scott? Push her lotion‑coated finger into your asshole while she sucked your cock?" asked Karelle, knowing the effect her question would have on me.
"And how did that feel?"
God, my cock was really hardening, and it was getting very uncomfortable. I shifted in my seat.
"It felt fucking great."
Again: "Eeuww." But not all of the girls joined in this time expressing their revulsion.
"Ladies, Scott is squirming. Would anyone like to guess why?"
The brunette who had chastised the girl about using graphic language had apparently completely overcome her reticence to use the vernacular. She said, "Because he's springing a boner just hearing you describe it, Miss Matthews." The group laughed at that.
It was true.
"Why don't you show us, Scott," said Karelle.
You could have heard a pin drop at that point. The coeds, shocked expressions on their faces, didn't move. They just looked at me.
"We talked about this, didn't we, Scott?" Karelle asked.
Naked in front of these women. Completely naked while they sat, fully clothed and comfortable, looking at me. Listening to me tell them why I liked being fucked with a strap‑on. Watching my erect cock prove convincingly that I was turned on by everything connected with a woman strapping on a dildo and using it to fuck me in the ass.
I masturbated right after reading the words in the email Karelle had sent me explaining that I would be required to do this. Now that I was actually in the situation, though, I didn't know if I could go through with it.
Karelle read the look on my face. "Let's make it easy for you. Take off your shirt while you finish telling us about your first time." She scooted back into her seat, getting comfortable. "Ladies, this would be a good time to grab a drink from the fridge if you need a refill. You won't want to miss Mr. Gooding's story."
A few of the girls got up to refresh their drinks. The others rearranged themselves in their seats like a group of fifth‑graders eager for story time. Karelle looked at me expectantly.
The incredible naughtiness of the situation triggered something in my brain that must have sent even more blood down to my hardening cock, causing the absolute necessity of adjusting myself in front of the girls.
"He's getting a stiffy," pointed out one of the blondes.
This is one of the other reasons the whole strap‑on experience is thrilling: you have to admit that it excites you. You have to abandon every last shred of propriety and confess that you -- the man, the macho guy, the aggressor, the horny stud, the perpetrator, the predator to the female prey---want a woman to fuck YOU. It's not supposed to be that way, and therein lies one of the most powerful things that draws me to it. Coupled with the intense physical pleasure (lots of nerve endings in the anus, I understand) and the total surrender of allowing yourself to be penetrated, the embarrassing admission that you want her to objectify your ass for her own pleasure (and yours, most definitely) is a huge turn‑on for me. I adore that the woman knows it and uses that knowledge to tease me, to draw out my anticipation, to excite me and herself while she plays with my mind in preparation for playing with my ass. I have to let her know that I am there for her pleasure, that I am there so that she can get off by using me. I have to tell her that I am her sextoy.
So I continued the description of my initiation, knowing that I would be admitting all these reasons that being fucked in the ass by a woman excites me to the group of women in front of me.
"I don't know where she got the lotion. A guy doesn't notice a lot of things when a girl is giving him a blowjob," I said, unbuttoning my shirt. I pulled the shirttails from my pants. "I asked her what she was doing, and she looked up at me, my cock still in her mouth, and she smiled---at least as much as a woman can do that with a mouthful of dick." I slid the shirt off, dropped it to the floor and sat back in the chair. "That was the instant that she deep‑throated me while inching her finger into my asshole."
"Shit," whispered one of the girls.
"I couldn't believe the sensations. She had my entire cock down her throat, and she was slowly pushing her finger up inside me. The whole thing felt fantastic, just incredible. Maybe if she hadn't been sucking me off while penetrating me I wouldn't have liked the feeling in my ass. But what she was doing, all of it together, just really drove me crazy."
I adjusted myself again.
"How old was this woman?" asked Celia.
"I don't know. She was older than me. Maybe 30."
Karelle interjected. "I bet you're asking because you wonder how a woman would even think to do something like that, right, Celia?"
The girl nodded.
"So you haven't thought about doing it?" asked Karelle. Celia shook her head. "Have any of you ever had your finger inside a man?"
A round of "Nos" followed. These were all complete newbies to the concept of being the penetrator. Karelle looked at me and grinned. "Well, tonight Scott will surrender his ass to any of you who want to try it out."
Holy shit. That hadn't been in any of the emails Karelle had teased me with leading up to this incredible experience. My shocked expression seemed to please her, maybe even turn her on a bit. Or a lot.
She continued: "Your pledge mistress has indicated that all of you, having made it through initiation, should be rewarded in some way. However, she has totaled the demerits each of you received while you were pledges, and the one among you with the fewest demerits will get a very special reward. All of you, though, have earned the right to find out how thrilling it is to have a naked man open himself up to you and beg you to finger‑fuck him in the ass. Maybe his explanations tonight will convince some of you that you'd like to try it," said Karelle, leaning forward slightly in her chair. "When you're inside him, you control him."
I searched their faces. A thoughtful expression on a couple of the girls told me that tonight I would be surrendering my ass to probing fingers new to the experience of penetrating a male, and I would have to beg those girls to do it to me. Karelle was pushing all my buttons, torturing me by intensifying this entire experience in ways that played on all the facets of the strap‑on encounter that make it insanely exciting for me. One of them is being told to ask---to beg---for the pleasure I know the woman will give me. Maybe that's a turn‑on because I know it intensifies her feeling of power and control. Or maybe it's because hearing myself beg to be fucked (or, sometimes when the woman has orchestrated truly embarrassing situations, begging NOT to be fucked) is such a blatant statement of how I've put my sexual satisfaction completely in her control. There's also the possibility that being in a strap‑on scenario just automatically makes me revel in the freedom to be a wanton, shameless, eager‑to‑confirm‑it, complete and total slut. That's something a guy NEVER gets to do anywhere else.
"Now the shoes and socks as you continue your description," prompted Karelle.
What the hell, I thought. I was living a fantasy, and being naked in front of them would at least put an end to the discomfort of my trapped, throbbing cock. I leaned down and took off my shoes and socks, placing them next to my shirt on the floor.
"It only took a few seconds of her deep‑throating me while she pushed her finger in and out of me before I came like I've never come in my life," I said, raising up from removing my shoes and shoes and socks to sag against the back of the chair. "After I came, I asked her what the hell she thought she was doing."
"The belt, Scott," said Karelle, a hint of impatience creeping into her voice.
As I unbuckled my belt, the doubt again surfaced. Could I do this? I continued, slowly. "She didn't answer me. She asked a question instead. 'Did you like it?' was all she would say, even when I started to get upset with her. 'Did you like it?' she kept asking. Finally, I cooled down, thought about it for a minute, and I said, 'Yes.'" Without prompting from Karelle, I had unhooked my trousers. "I admitted to her that I liked it when she slid her finger inside me."
"Were you embarrassed? Was she making fun of you?" asked one of the blondes.
"Excellent questions, Joanne. Let's get Scott's answers while he steps out of his slacks." Karelle turned her head to address me. "Stand up while you drop trou, Scott."
I did as I was told. After my trousers hit the floor, I answered, "Yes, it was really embarrassing to tell her I liked it. I was afraid she would think I was a pervert or something. But after I thought about what happened that night, I knew she wasn't making fun of me -- she was just getting me to put aside any automatic assumptions about what she did to me in order to realize it felt great." As I finished answering the girl's questions, I stepped out of the pile of fabric at my ankles, and in doing so looked down to realize with horror that the front of my briefs---white and made of some pretty thin material (Karelle had mailed them to me with instructions to wear them this evening)---were clearly wet and sticky with pre‑cum leakage. That meant the front panel of the briefs had formed itself snugly around the outline of my cock. Only the elastic band at the top of the briefs was preventing the head of my dick from popping out into view.
"He really does get off on this," said Joanne. "He's hard and dripping."