The Bully Pt. 10

Samantha and I progressed quickly in our relationship, and shortly after our first hook-up, we were cohabiting. Not in the legal sense that I had changed my address on my Driver License or my auto insurance, but as each day came to a close it was evident that we would be spending the night together.

Samantha was so much more mature than Lela and I found myself able to talk to her about almost anything. Samantha was aware of my limited dating history, my period of servitude to John, and the complex dynamic between John, Lela and I. One night as we were lying in bed after a sensual lovemaking session and several glasses of wine, the subject of anal-sex came up.

"Did John ever take you by force, Mark?" Samantha began, her head resting on my shoulder as she raked her nails across my chest.

"Occasionally he butt-fucked me with a bit more brutality," I said candidly. "But most of the time he used me when he was horny, just to blow his load."

"Have you ever been pegged by a woman?" my girlfriend asked, the interest evident in her voice. "Would you be open to trying it?"

"I'm not sure, Samantha," I said nervously. "My experience with anal-sex has taught me that it can be quite painful."

"Not if we take it really slow," she countered. "I have some Anal-Ease which has a topical analgesic in it which acts as a numbing agent. I also have a pencil sized strap-on dildo that is great for beginners," she offered optimistically. "I promise I won't hurt you if you consent to it."

"If I consent to it, Samantha?" I said with a surprised look on my face. "How else would you peg a guy, other than consensually?"

"Well," she began sheepishly, "pegging can also be used as a punishment, in which case it is more about power than sex."

We had both had several glasses of wine and the conversation was flowing freely. Samantha had already shared with me that she had enjoyed a total of six sex-partners prior to me, so I asked the obvious question.

"Have you pegged all of your ex-boyfriends, Samantha?" I asked with a nervous laugh. "And was John's pegging consensual or punitive?"

"Good question," Samantha said with a twinkle in her eye. "I did anally penetrate all of my exes in a loving consensual manner. John's pegging was somewhere in the middle. Under the assumption that catering to my needs first would earn him additional brownie points, John gave me his full consent and bent over the desk voluntarily. However, once he was in my desired position, I used some neckties to restrain him, and I guess from that point on it was punishment. John was an Alpha Male and a total player. When he asked me out I said yes just so that I could burst his bubble, take him down a notch or two. John needed a good butt-fucking to put him in his place."

"Is that your thing, Samantha?" I asked naively. "Using a strap-on on your partner?"

"I find it empowering to bend a man over my desk, attach a strap-on phallus to my harness and butt-fuck a guy into submission," she admitted. "But it doesn't have to be painful, Mark. If we go slow, and I use plenty of analgesic lubricant we can enjoy the role-reversal without any discomfort. Are you willing to trust me and submit to me?"

My eyes widened as I considered the prospect that I was the only man that Samantha had made love to that she hadn't pegged.

"How many guys have submitted to you, Samantha?" I asked incredulously.

"About twice as many as I have made love to," Samantha responded candidly, her inhibitions lowered by the alcohol she had consumed. "Give or take," she added with a giggle. "You are the only man who I have ever kissed that hasn't yet submitted to my strap-on."

"How many were consensual and how many were punishment?" I asked, swallowing hard as we went down this rabbit hole.

"The lines are blurry, baby," Samantha replied, giggling more freely now. "In my personal life mostly all consensual with a couple of exceptions, and John was probably on the fence. The work-related encounters were all punitive, no exceptions."

"Work-related," I repeated with a chuckle. "You are funny Samantha."

Our late night chats were always candid and seemingly free of agenda, although Samantha would raise the prospect of pegging me quite frequently. Finally, after we had both had our defenses lowered by lots of alcohol, I tried to get to the root of it.

"Why are you so fascinated by the prospect of pegging me, Samantha?" I asked her, my inebriation making me more confident.

"It's not just you that I want to butt-fuck, Mark," Samantha slurred, a little worse for the wine. "It's all men. I was severely disadvantaged in College and Law School by virtue of my gender. Even when I graduated top of my class, there were rumors that I had slept my way through College. In Law School I had to work harder than the men just to be noticed. Even when I got hired by our Law Firm, and was assigned Danny Marshall as my mentor, he spent the first six months trying to get into my panties. Most men are pigs and I relish any opportunity to bend them over my desk, consensually or punitively."

Our drunken conversation veered off in a different direction and I never bent over Samantha's desk that night. I loved this woman but I had a feeling that in her core Samantha harbored a deep resentment of the males of our species.

Once we established that we were a couple, Samantha and I discussed whether or not to tell anyone else at the law firm, as Samantha didn't want to upset the dynamic in the work place.

"I need to inform Stephanie, Head of Human Resources, at the very least," Samantha told me. "And the two other members of the Senior Management Team."

"None of your subordinates need to know right, Samantha?" I asked tentatively, not wishing to alienate any of my peers.

"Just Danny," she said reluctantly. "Danny Marshall, the fucking cock-hound" she added for my benefit. "Prior to my last promotion Mr. Marshall ran the office and it was a total boys' club. Technically I am now Danny's boss, but he is a misogynistic prick and somebody that I need on my side. I will let him know as a professional courtesy, but that should do it."

I was comfortable with the fact that only four senior members of the legal team would be informed of the consensual relationship between Samantha and I. It seemed prudent to inform Human Resources, and the other three individuals were trusted, long-term employees who had a valid reason to be aware of the situation.

I did tell Lela, but only because she asked me directly in one of our infrequent conversations, and I viewed her as too emotionally fragile and unstable to lie to her. Predictably, she was going through her own bullshit with her latest loser boyfriend.

Ever since I cut Lela loose she had entered into the first of many in a series of abusive relationships. She met her first new boyfriend, Ratt, at a local tattoo parlor while she was considering getting her first ever tattoo. Lela wanted a rose on the back of her neck, and as she signed the consent forms and age-verification documents, Ratt approached her and made some small talk. By this time in Lela's life she was damaged goods, and there was no hiding her self-loathing and her distinct feeling of her lack of worth. Ratt had seen his fair share of downtrodden girls, and made a beeline for Lela.

Ratt ended up tattooing Lela that day, drawing a large red rose at the base of her skull, the placement of which mystified me because it would be hidden by her hair. Ratt convinced Lela to let him sign her first tattoo, and upon securing her consent he inscribed his name in large, black, cursive scrawl just above the rose. Lela hung out in the tattoo parlor until closing time, and Ratt ended up going home with her to her apartment. I am not sure how that relationship ever lasted two years, but during that time Ratt beat her up twice, forced himself on her on multiple occasions, and persuaded her to add the word "CumSlut" beneath the rose tattoo. Unbeknownst to Lela, Ratt also added an apostrophe and a small letter "s" to his name during the second session.

I still saw Lela fairly regularly, although most of our interaction involved her asking to borrow money. I could see the self-hatred in her eyes when we would meet for coffee, or at the local park. Life had beaten her down, and her bad choices in men had made her feel even less deserving of true love. Every single time I gave her money she offered me sexual favors in return, and I think the fact that I turned her down each time, made her feel even less worthy. One time when we met in the park it was really warm out and Lela was wearing cut-off jeans and a bikini top. She had her hair up in a bun, and she asked me to put some sunblock on her neck and shoulders.

I still had some strong feelings for my first love, despite the fact that I was in a committed, monogamous relationship with Samantha. So it pained me to have to see her neck tattoo as I applied sunblock to her upper body, particularly as the cursive seemed to read "Ratt's CumSlut"

"You know Lela," I said, as I rubbed the SPF 50 lotion into her neck, "You deserve a better man than Ratt."

"I am a dirty CumSlut, Mark," Lela said quietly, barely able to look me in the eye. "John has told me that since day one."

I don't know if our meeting in the park that summer's day was the catalyst for change. However, shortly after I gave Lela five hundred dollars to help make ends meet, and I declined the offer of a blowjob in the men's bathroom stall, Lela left Ratt and checked into a seedy motel. Of course, as the saying goes, you are only as good as your options. The cheap downtown motel, and its motley crew of transient inhabitants, severely limited Lela's options, and within two weeks she had hooked up with a hulk of a guy who was dealing steroids.

I say hulk of a guy for two reasons. Firstly, presumably due to sampling much of his own merchandise, he was colossal in size. In addition, his episodes of steroid-induced rage made him appear to have some of the same anger-control issues as the Marvel Comics SuperHero. Hulk, as Lela and I referred to him, beat Lela on numerous occasions, hospitalizing her twice in the process. He was much more territorial of Lela too, restricting my access to her for several weeks at a time. Lela still reached out to me for the occasional loan, although as she got harder from being around such scum, it became easier for me to turn down her offers of oral-sex in exchange for my financial assistance.

Lela was arrested twice for possession of steroids and paraphernalia, earning community service on each occasion. It was evident to me that Hulk was using Lela as a mule to transport his drugs, and I warned her of the consequences of another arrest. Fortunately for Lela, it was Hulk who was arrested first, and his assault on two police officers ensured that he was going to be incarcerated for a long time.

I saw Lela more regularly after Hulk went to prison, and she seemed to come out of the darkness a little. However, with her lack of self-esteem, and her new-found habit of referring to herself as "CumSlut" it wasn't long before she submitted to the next loser boyfriend. This went on for years, and much to my dismay Lela even went back to Hulk after his release from prison.

Once I started dating Samantha I informed her of my ongoing friendship with Lela, and Samantha assured me that she was fine with it.

Samantha knew that Lela was my first girlfriend and understood the gravity of my feelings for my first true love. In contrast to Lela, Samantha was very self-confident, and was not threatened in any way by my continued friendship with the younger woman. Lela was aware that I was in a committed, monogamous relationship, but every time I hung out with her she tested my resolve to be faithful. At first I laughed it off, but as Lela constantly offered me unconditional sex it became harder to ignore the possibility of a no strings attached release.

"Just take me into the gender-neutral bathrooms and blow your load on me, Mark," Lela whispered one day as we walked around the mall. "Samantha need never know that I am your side-piece. I am happy to be a cum-receptacle for you to use whenever you are horny."

It became increasingly difficult to turn Lela down, particularly as Samantha and I had cooled off a little in the sex department. This was partly due to the fact that every time we got intimate, Samantha asked me to let her butt-fuck me with her strap-on. Samantha was reasonably open-minded in the bedroom, but had clearly defined hard-limits. Lela, by contrast, assured me repeatedly that nothing was off-limits to me. As my sexual horizons broadened, I regretted my limited sexual history with Lela, and she made it crystal clear that she was more than happy to make it up to me.

"You can do anything that your heart desires to me," Lela said on another occasion. "You must have some unfulfilled fantasies. I love being used by men."

One day, as we sat sharing a table at a local coffee shop, our conversation took a serious turn. Lela informed me that she had been offered a job at an escort agency that specialized in submissive women. Initially I thought it was a terrible idea, a sure-fire way to lower her already questionable self-esteem. However, as Lela went over the pay-structure, housing arrangements, security procedures, and company benefits, it occurred to me that this might actually be a safer environment than life in the motel with the scum of the earth.

"Well, Lela," I said jokingly, "if you are going to get roughed-up you may as well get paid for it."

"Exactly, Mark," Lela responded. "I am going to offer very specific services for the sophisticated men who hire me," she added, as if she had given the matter much thought. "I am going to replicate the Klixen experience, too. Maybe I could practice on you?"

At this point in my life I was in a committed relationship with Samantha, and while we still enjoyed a satisfying sex-life, the demands of our careers left little time for protracted lovemaking sessions, and our encounters became once a week affairs. Lela had caught me in a particularly weak moment, and my hesitation must have transmitted that, because she upped the ante.

"Maybe you would rather accompany me to my photo-shoot next week?" she added playfully. "It's the least that I can do since you offered to front me the money for my portfolio."

With the advent of the internet, escort agencies had revised their marketing campaigns, evolving from simple glossy cards left in local phone booths, to full-on photographic portfolios. Recently, as TikTok gained in popularity, most escorts had added a short video to their online presence. Lela planned to summarize her Klixen blowjob experience in her brief video, and was offering to use me as her model. If I had to be honest, the thought of it made me rock-hard.

"We'll see, Lela," I said, trying not to allow my arousal to influence my decision-making ability.

As it turned out, I ended up attending Lela's photo session, but rather out of necessity than desire. Due to the propensity of human trafficking in the escort business, the photographer required the session to be paid by Bank Transfer and he needed me there to sign certain required documents. I spoke to him at length before I acquiesced, having realized that this was a non-negotiable.

When I mentioned it to Samantha she voiced some concerns.

"Are you sure about this, Mark?" she said nervously. "You are going to be in a sexually-charged environment with your ex-girlfriend. Is this the best idea, especially as we haven't been as active in the boudoir lately?"

"I can control myself around Lela," I said confidently. "Although if you want to give me a little incentive to be a good boy, I am down for that."

"I bet you are, stud," Samantha teased. "I'll tell you what. You keep your hands to yourself at the photo studio, and when you get home I will be wearing your favorite pink suit, with my garter-belt and stockings."

I truly loved Samantha, and as we shared an extended hug, I told her so.

When I arrived at the photo-shoot, the first thing that surprised me was the professionalism displayed by the crew. The studio was spotless, beautifully lit, and appeared to be a very sterile environment. I paid for the studio time via Bank Transfer, signed a statement of identity and an affidavit of non-coercion on my part, and then stood off to one side of the studio, awaiting Lela's arrival.

When Lela arrived at the studio she was in a panic as her model had canceled at the last minute. Lela had elected to use one of the male escorts from the agency as her partner in the photo-shoot, and he had let her down badly. We were on the clock, at three hundred dollars per hour, and Lela approached me with a frantic look on her face.

"Mark, will you do the shoot with me?" she practically begged. "I am desperate."

I considered it for the briefest of moments, before reminding myself that I was in a committed relationship, and these pictures were going online. There was just no way I was willing to put myself in such a compromising position.

"I can grab one of the sound technicians if you just need a fuck-buddy," the Director offered, clearly no stranger to these inadvertent mishaps.

"Ew," Lela said with her nose wrinkled in disgust, having suddenly become virtuous again. "No way. Can you just give me a minute to work things out?"

"Sure," the Director answered. "It's your money."

Turning her attention back to me, Lela intertwined her arm with mine, snuggled in close to me and took another run at me.

"Mark, please," she began in an imploring tone. "I am begging you."

As much as I wanted to participate, to be the lucky recipient of Lela's version of a Klixen blowjob, I knew I had to resist out of respect for Samantha. Lela pleaded with me to no avail, and then finally a dark cloud came over her face and she underwent a total attitude adjustment, transforming into a total bitch.

"Well then, you leave me no choice," Lela said coldly. "I really didn't want to do this, Mark," she continued, as she picked up her phone and pressed the number of one of her contacts.

"Mark won't do it," she said dejectedly. "What time can you get here?"

With her replacement model secured, Lela approached the Director and had a brief conversation with him. Whatever she told him spurred him into action, because he began to issue directions to the assembled staff.

"Ok, guys," the Director began authoritatively. "Lela's partner will be here in twenty minutes. Let's start on some of the solo photos."

As the still photographer and the video cameraman got into position, the lighting guy began to take some last minute measurements, and the sound guy moved his mic boom around to check the audio. After ensuring that everything was proceeding as expected, the Director turned to Lela.

"Things move fast on set," he began. "We want to get as much out of the hour as possible so there isn't time for niceties and platitudes. I will give clear directions and expect everyone to move quickly to that end. Why don't you get comfortable, Lela?" the Director added firmly.

Apparently in the escort business getting comfortable has an alternative meaning, because Lela removed the outer layer of her clothing to reveal that she was dressed in a black leather micro-mini skirt, matching leather bra, and a dog collar. My heart sank as I saw my lovely ex-girlfriend looking like a submissive who was definitely for sale.

I had never used an escort agency before, but back in my college days I had browsed their websites on occasion, fantasizing what it would be like to fuck one of the gorgeous East European women, had I even had the price of entry. High-class escorts typically had stylized photo-shoots, wearing designer dresses or expensive lingerie. They were often photographed in exotic locales, or relaxing in a chaise lounge as if they lived a life of leisure. The sex was hinted at, never overtly advertised. You were buying time, not a specific sex-act.