May's Mission

I came to know May over a protracted period of months, the first meeting during which was by complete happenstance. The stereotypical woman stranded on the side of the road, not too far from home. Perhaps it had just happened, but I remember being a bit shocked that no one before me had stopped to help her. For me, a car guy and somewhat of a part time empath, not stopping was out of the question, especially when it came to women and mechanical things. But I remember having to be careful, lest she think that I was some kind of an axe murderer or something.

I pulled in front of her and only partially got out of the car.

"Problem?" I asked looking back. She was kind of cute.

"Well, yes, I got a flat and have no way to fix it. I called somebody, but they won't be here for an hour." May responded.

"I think we can do better than an hour. Do you mind if I take a look?" May nodded.

Walking over, I introduced myself while still maintaining my distance. "I'm Rob; I am kind of a car guy..."

Head motioning in the general direction of my recently restored, mid 80's, silver 911, May responded with a laugh: "Yes, I can kind of see that. I'm May."

Ice broken.

To make a short story long, May had been driving around in a car with no jack, no lug wrench and spare that was all but flat. "Typical", I remember thinking to myself. I explained the situation, while refraining from dressing her down. I remember also thinking that perhaps that would come later. I surmised quickly that the 19mm Porsche lug nut wrench that I had with me was way too big for a Honda. But I also had a set of rather nice, forged steel box ends that might work and one of them did. Thankfully, the nuts weren't on too tight and I did the tire with a portable compressor that I keep for just such occasions. Problem solved.

"Well, I am glad you found me!" May smiling as I opened the car door for her. She was a sweetheart.

Handing her a business card, I joked: "Well, if you ever get another flat, you now know who to call. I am glad I could help."

I almost started walking away, but remembered and walked back: "Hey, I would be happy to help you find the stuff you really should have for the car should this happen again."

She hesitated slightly with a "no, that's OK", but I persisted. She was smart and here was a car guy offering to help her find critical car parts. "Well, OK, that would be really nice of you." May smiling again. She definitely was cute. I took the needed info, including her phone number, promising to burn it and never call her again once the parts were procured and the transaction completed.

"Oh, no, you may call me anytime, you're a respectable guy." If she only knew. But this shit never happens to me. It's always a battle. Finally a woman who came on a little to me.

About a week later, I called her advising that I had what she needed and in those words. Little did I know that they were the foreshadowing of our soon to be relationship.

"Well, I'll tell you what", May proposed, "why don't you come over for dinner since we live kind of close anyway."

To me, that sounded like fun, so of course I agreed. Greeting me with a peck, she had dinner all ready and so we ate and drank wine. A bit too much wine, I might add. I think she made sure of this so that I wasn't as guarded as I would have been sober. She asked if I would like to watch a movie which we did, but we really didn't. We were more interested in each other instead and wound up talking and joking the night away. That night, I began to like May very much and felt that there was something different, something edgy about her that you just don't find in the average woman. It was really hard to explain, but I was quite attracted to her and hoped that I wouldn't blow it somehow. We even had a down to earth discussion as to how that happens. She was great and I let her in rather quickly and she seemed to reciprocate.

While our friendship grew over the ensuing months, our physical contact was limited to only the perfunctory kiss hello and goodbye. Sure, I would hug her often, but she seemed a bit guarded and somewhat distant physically and I could not help but wonder why. I would soon find out. It wasn't me.

One night after a dinner at her place, we got liquored up pretty good. I began the typical guy advances, but she stood up, shutting the party down abruptly. I thought that I had really pissed her off.

I'm sorry" I said, "I just like you and I am becoming physically attracted to you."

"No, it's not you, it's me" said May. I had no idea what the fuck she was talking about.

"I have never been with a guy" May said.

"Well, that's OK, we can take it easy, I don't mind. I like you as a person first" I reasoned, finding her declaration rather hard to believe. And I told her that.

"Well, you don't understand" May added. "I'm a special girl"

I started getting a little edgy: "Well yes, I agree and you are certainly special to me."

"No, Rob, you still don't get it. Stand up, come behind me and put your arms around me."

I did as she asked and May, wearing a somewhat flimsy skirt - and a great pair of high heels I might add - pulled my hand lower, beneath her skirt and panties and down between her legs. How I never noticed this before was beyond me, but I now had my hand around a rather nice set of cock and balls, a set that I would have been proud of. I tried to "act normal" and not be shocked, but that would have been a bit dishonest. I was and she knew that I was. Conversely, however, I didn't have an urge to run out the door either as it all was a bit exciting for me.

"Do you see now what I mean?" May asked.

"Well, yes, OK, but that doesn't change May, the person, does it?"

She turned and I could now see that tears had welled up in her eyes. This told me that she liked me, our relationship and wanted to preserve it. "No, I am still the same May." She then kissed me and kissed me with the most passion she ever had. She cried some more, but I held her tight, wiped her eyes and caressed her hair. Not only did she have feelings for me, she had put those feelings in the palm of my hand, for me to do with what I wished. She was open and vulnerable.

"Then what's the big fucking deal?" I said rather loudly. She smiled and started laughing, her tears dripping away. At that moment, I didn't really care about what was down below, I only cared about her.

"But I want to be with a guy, and not just any guy. I want to be with you" May said, regaining some composure. "You know me and you know how to handle me. You've shown me that over the last few months. I know you care and that I can trust you."

She was right. May was special to me, perhaps even more so now. I was a velvet lined safe for May's feelings and secrets. And I made sure that only she had the combination.

I texted May the room number soon after I entered the motel room; she already knew where we were meeting. It was well after dark and, outside, the place was not very well lit - typical of a "B" rated facility - but the gloom somehow added to the suspense. Minutes later, a pair of headlights briefly illuminated the cheap, but thick curtains, followed by the sound of two car doors closing. I found myself, in the few ensuing seconds before the door opened, thinking that I had to make sure to immediately assume and maintain the role of master here and take firm control of my two willing, but perhaps unwitting, participants.

May's friend Andi was a rather average looking, maybe mid-20's ish, petite little filly, with mosquito bite tits. She got cuter as the lights were turned down, or perhaps if you gradually had more to drink. Kind of a quiet, mousey little thing, but she had the one attribute that always seems to be in short supply: enthusiasm. I was immediately attracted to Andi for this reason alone.

I was not sure that May told her why she was there or what we were about to do, but her eager body language made her a natural fit for the intended proceedings. She was May's "girl" and she was curious. I would also add "courageous" to Andi's resume, since it took a serious amount of balls for her to show up to a secret, and most likely, in her mind, nefarious meeting. May's relationship with Andi centered around Andi's "for hire" provision of domestic chores, but I don't think Andi had complete knowledge of what May was about. Nevertheless, the two apparently knew each other well. I would also think that May surmised that Andi's subordinate domestic role and curiosity would play well as May's "helper" in this meeting and, ultimately, with May's fulfillment of her sexual need.

A need that both Andi and I were to fulfill.

In the dim motel room lighting, I kissed May lightly on the cheek as she entered and hugged her while she introduced Andi to me. While they both were dressed neatly, I had made sure that I slightly out dressed them with a more formal ensemble, including a tie. I explained to Andi that she was here to help May, but I left my explanation intentionally vague. With the formalities over and with the two standing in the middle of the room between the two beds, I sat down on a flimsy desk chair, facing them, not saying a word. They began to fidget and, I presume, wonder just what the fuck I had in mind.

It was time to give them something to do.

"Andi dear?"

"Yes?"

"Please undress May."

Andi just looked at me but, in the corner of my eye, I caught May fighting a smile.

A few seconds passed.

"Andi? I asked you to undress May."

"Please remove all of May's clothes."

"You are May's servant and May should not have to remove her own clothes."

"That's her servant's job. In other words, that's your job."

"And do it slowly, if you don't mind. And from behind."

Incredibly, Andi remained in a state of suspended animation, my firm request clearly amounting to a complete violation of Andi's traditional relationship with May. No matter, I had a mission and I was starting to make the transition from role play dom to actually losing my patience.

But, in retrospect, Andi's inaction was a godsend. This would be a great ice breaker and a way to further establish my dominance.

Reading my body language, May's snarky smile had completely disappeared. Removing my leather belt, I got up from the chair while Andi simultaneously lunged for the door. I caught her just as she grasped the knob and threw her on the closest bed in a not so nice way. She looked back at me, with her eyes as wide as saucers.

Sliding her off the bed by a leg, I snapped: "When I tell you to do something, I want you to do it."

With her struggling, I managed to undo her jeans and pull both those and her wispy panties down to about her knees. At probably less than 100 pounds soaking wet, she was easy prey. She knew what was coming, of course, and I pulled her back over to the chair I had just left and draped her over my lap.

"Please don't hurt her" May said, now clearly getting worried.

"She is here for you and now she has to be taught a lesson" I answered, looking at May.

During this exchange, Andi's desire to resist seemed to gradually wane. Perhaps she was looking forward to her punishment and I just simply didn't know her inclinations. Or perhaps she just accepted that she was powerless. It didn't matter. Either way, she was going to get it.

"How many, May?" I said as I folded the belt over, putting May on the spot. Andi strained to look up at May while May decided her fate.

"Would three be OK?" May asked. I could tell that May was getting sheepish - Andi knew just how to get to May. Nevertheless, my goal was to establish my dominance, not to hurt May's good heart by excessively punishing Andi. So, I had to be careful. I had to walk the tightrope.

I altered my course slightly. Part of the fun of administrating punishment is to give the subject some time to think about it. The anticipation scares the shit out of them. So, I stretched it out.

"What do you think you deserve, Andi? Three?" I said.

No answer.

"I asked you a question, Andi."

"Three is OK, I guess." whimpered Andi, now looking down at the floor.

"What do you mean 'you guess'"? "Is three OK or not"

Before she answered, I added a firm "I mean appropriate for your disobedience".

"Yes. Three." Her voice was now trembling. Now limp across my lap, she was almost crying, exhibiting clear signs of surrender and simply awaiting her punishment. And the pain.

I couldn't help but feel sorry for her. Leather belts fucking hurt and she was out of resistance cards.

"Yes, OK. Three this time" I said. Implying that the punishment would be incrementally greater for any further infractions.

"We're all in agreement then, right?" May's look now turned more to one of regret, since she had specified the number of lashes. May's soft heartedness was a loving quality and was what had attracted me to her in the first place. I therefore had to be really careful not to damage the trust.

Looking at May and then at Andi I said: "I promise to be quick. But, yes, this will hurt."

I rubbed the cool leather across Andi's rather attractive and compact rear end. I could feel her tense up. I let the belt linger a bit more. Shamelessly, I couldn't help but feel a twinge of desire to fuck Andi right there in her cute little ass. But I first had serious business to attend to.

I again dragged the leather across Andi's tensioned butt and then pulled the strap completely off her ass to prepare a throw. And I took my time about it. I could feel her brace. I waited a few seconds more to let the anticipation build. Andi started to shake.

Facing the floor, Andi couldn't see that I was unfurling the strap.

I was letting her off the hook.

A few more seconds ticked by.

"OK, you may get up. I have frightened you and that is punishment enough." The mindfuck was over.

As she got up from my lap, I could see the relief in her face, her watery eyes and a single teardrop depart her nose. Degraded and frightened, I truly felt sorry for Andi, but I couldn't let her know that.

"Thank you, Rob, I love you. I'm sorry for not obeying you." She kissed my cheek as she wiped the remaining tears from her eyes. I weakened a little and helped her, my own heart now feeling a little better.

Back in "dom" mode, I said: "Don't apologize to me, apologize to May. You are May's servant, not mine". With the firm accent on "May".

Pulling her jeans and panties back up and trying to regain some of her composure as a woman, she wobbled over to May and hugged her, her unzipped pants sliding seductively back down. It was quite a sight. May hugged back and mouthed "Thank you" to me. I winked back at May. Trust reestablished.

Without any further provocation, Andi released her hug and began unbuttoning May's blouse, interrupted only by the occasional sniffle. And she even did it from behind. Now, we were getting somewhere.

May's backside figure, while not quite supermodel shapely, was certainly shapely enough. My past exploratory and frequent halfhearted gropes during our "good to see you" kisses certainly confirmed that. With May now naked above, there was no warning or indication for poor Andi as to what lay below. I quietly mused how funny it is how we all "assume". I certainly had.

Andi undid May's jeans and, rather sensuously, helped her out of them. I was proud of her. Andi was now at a new level. She had been broken in as a sex servant, which was all part of the plan. But it wouldn't have happened properly had she not initially resisted. The mission was moving forward.

By this time, May was now rapidly running out of garments to shed. Only her black fishnet panties and high heels remained and May was careful to keep her back towards Andi while she mostly faced me.

Just as it was for me, little Andi was about to get the surprise of her life.

"Leave her high heels on" I said. Andi turned, smiled at me and dutifully nodded. I started liking her even more. Like May, she was a good egg. We're going to have fun tonight.

Andi slipped her thumbs under May's panties at each hip and began to lower them slowly, sensually. But there was something wrong. Something was holding them up. They were descending, but it wasn't smooth sailing. I could see May trying not to giggle, but Andi was completely perplexed. I could tell that Andi wanted to reach around to fix the problem, but was afraid that doing so would violate May's privacy. It was a quite amusing dynamic.

I could also tell that May was getting aroused during the process but, before she got too far along, she took Andi's right hand as she did with mine and slid it under her panties, allowing Andi's hand to completely envelope May's growing package. To say that there was a look of surprise on Andi's face would amount to a giant understatement. Her mouth agog and her eyes as wide as saucers, Andi looked at me in amazement. I could not help but laugh. As a dom, I'm allowed at least one.

But this is where it got interesting. Rather than withdrawing her hand, Andi kept it there and started working May's cock. Apparently, Andi was no stranger to cocks and fucking. Just perfect.

Putting fuel on the fire, I ordered Andi: "That's right work it. I know May wants you to. Tease her. Make her rock hard. Make May cum."

May's eyes started closing with her mouth slightly open as Andi worked her evil, her hand still under the fishnet, stroking and squeezing. May's cock was reacting accordingly, now completely distorting the fishnet to the point where it must have been uncomfortable.

I got up, moved behind Andi and gently disrobed her, my right hand exploring her pussy, which was soaking wet. Then, I firmly pulled May's hair so her head was tilted back, and kissed her lips from behind. She was in heaven. I then finished Andi's panty removal job, leaving May standing naked in the middle of the room, perched atop high heels with a burgeoning hard-on. Even as a heterosexual male, it was difficult not to get aroused.

May was getting weak kneed from Andi's playing, so I reorganized our little orgy with May on all fours on the bed with Andi upside down, her face just under May's surging, rock hard cock. It was clear that May oozing cock wouldn't need much more stimulation.

"Andi?" I inquired.

"Yes?" Andi replied

"Suck May's cock" I ordered. With no hesitation, she obeyed.

I watched as Andi's tongue orbited May's cockhead a few times and then she engulfed the entire head. I heard an "aahh" leave Mays' lips. But then an even better idea evolved on my part. Since Andi's head was just about off the edge of the bed, I ordered May to face fuck Andi. Andi knew she didn't have much say in the matter, being trapped under May and my belt within easy reach. And this time, I would have used it. May's first couple of thrusts into Andi's gaping mouth were a bit tentative, so I smacked May hard on her ass.

"Do it right. Fuck her face. Don't you like to face fuck?" I said, raising my voice and assuming anyone with a cock just loves to face fuck someone.

"Andi owes you this for all the trouble she caused you before. If she loves you, she will take it."

Not a word of objection from Andi.

May, the delicate flower, didn't answer, but proceeded to repeatedly and now more aggressively plunge her stiffness well down Andi's throat, her balls audibly slapping Andi in the face. Amazingly, Andi didn't object a bit; a true blowjob queen, I guess, and any mercy that May might have felt for Andi during Andi's ordeal was now gone. With May consistently going balls deep, Andi occasionally gagged and drooled globs of cum and saliva out each corner of her mouth. I had never witnessed a face fuck in person and this was shaping up to be a good one.

At one point, the mucus in Andi's nose that had accumulated during her "over the knee" ordeal, made a spectacular nasal exit, making a further mess of Andi's face and providing even more lube for May's relentless oral thrusts. The stuff was everywhere, it was quite exciting to watch. Blobs began to permeate Andi's hair; it was all over her face and eyes and some rolled down to her ears. Strings of it linked May's cock and balls with Andi's face, mouth and hair. May kept it up tirelessly and Andi was beginning to fight a losing battle.