Trust is also paramount to expanding your sexual experiences and exploring your boundaries. What I will offer you is simple. I want you to be able to explore your desires, fantasies and boundaries with no judgment, no expectations and no regrets. In order to do that, I think you need to feel safe and protected. In that vein, simply say the word “watermelon” at any point and I will cease whatever we are doing. Do not use it lightly. Stretching one’s horizons should be a little uncomfortable after all.
I will post one last piece of the puzzle later today on the website. I only ask that you be open and honest with your replies as that will help me more effectively plan our time together. The questions I will ask may seem random or arbitrary, but they will give me a better idea about your sexual history, or lack thereof.
I very much look forward to seeing you soon.
Mark
A button at the bottom of the page read “Next”. I clicked and Mark’s latest note disappeared and was replaced by a clock counting down from four hours. My curiosity certainly was peaked to discover what Mark had planned next.
Two more fairly boring meetings, a salad from our cafeteria and some routine budget planning later, I closed the door to my office once again and returned to the website. The timer was ticking off the last few minutes of the four hour countdown. When it finally reached all zeroes the clock exploded into a thousand little pieces and was replaced by what appeared to be the beginnings of a questionnaire of some sort.
Summer’s Final Exam
1) When was the last time you had sex?
2) Last time you masturbated?
3) Do you use toys when you masturbate?
4) What is the kinkiest thing you have ever done?
5) Have you ever tried anal sex?
6) If yes to #5, did you enjoy it?
7) How many partners have you had in your past?
8) Ever been in or fantasized about a threesome?
9) If yes to #8, was it a MFM or FMF threesome?
10) Ever been with another woman before?
The questions continued on like that for several pages, some fairly simple, some shockingly explicit. I had to once again give Mark credit, he was very creative indeed. In between some of the questions, he had inserted pictures and short videos. One section compared various pictures and asked me to rate what I found more attractive. A picture of two topless women pressed up against one another kissing versus one of two men in a similar embrace. I found myself looking at that particular picture for quite awhile. One of the women bore a slight resemblance to my friend Julie, so it was hard at first to reconcile the truth behind finding that picture more attractive. I thought about it for awhile, but I quickly came to the conclusion that seeing two men together really did nothing for me, while it was much easier to objectively view the inherent beauty of the female form. Men’s bodies in general seemed to be hard (not necessarily a bad thing in some areas), angular and imposing, while women’s were curvy, soft and inviting.
Another section asked me to compare several video clips and judge on a scale of one to ten what was more arousing. One comparison was between a set of obvious porn stars, the man hung like something I’d last seen at the petting zoo, the woman’s giant breasts defying all laws of gravity and motion, and a couple of fairly normal looking amateurs. Even with the slight paunch on both of them, I found the normal looking couple much sexier overall. Perhaps it was because I could identify with the less than perfect body, or maybe it was just they seemed more “real” than their professional counterparts somehow.
A final section asked me to type out a short description of any fantasy I might have that had gone unfulfilled over the years of my marriage. I jotted down a quick fantasy of being tied up, something my ex-husband had shown no interest in, despite repeated hints. I think I had exerted such control over every other aspect of our lives, that maybe he had trouble believing this was one area where I wanted him to take charge once in awhile. This was nothing I would have ever vocalized to him however. Looking back I think I somehow expected him to just implicitly know what I wanted. And we wonder why men don’t understand us.
7
After I finished with the final “probing” question Mark had for me, another scrolled note appeared.
Summer,
One last item on our agenda. While I was fairly clear about fully intending to take control, I do so with a very healthy sense of humor and a heavy dose of reality. Having said that, which of the three following dates fit your schedule best? The three choices below will become clickable links by this time tomorrow. That will give me an opportunity to look through your answers and plan our first evening together accordingly. Your final instructions before we meet will be posted at that time.
Mark
Not too sure I really liked his use of the word “instructions” as if I were his servant, I nonetheless was still looking forward to seeing what he had in mind. My curiosity, and quite honestly, my libido, were running rampant at this point. Trying to put Mark out of my mind for now, I turned back to my work.
In all fairness and honesty I will have to admit to being a little worked up by the implications of Mark’s questions and the included pictures and videos. Alone in my empty bed that evening I managed to avoid major disruption in my study of the masturbatory arts by finding a spare pair of batteries floating around the nightstand junk drawer. I wondered idly as I drifted off to sleep if I should, in good faith, update my previous answer to Question #2.
After my usual morning routine of heavily self-medicating with caffeine, I managed to focus for a short time on shuffling some office paperwork through the system, with hardly a stray thought toward Mark’s website and my impending fate. Trying to not feel too foolish as I brought up the website and hit the refresh button ten times in a row, I was pleased to see the dates had been replaced by clickable links.
Giving up all pretense of trying to contain myself, I selected the closest date, the following Friday night, little more than a week away. As I clicked on the date, that familiar looking scroll appeared from the top of the screen.
Summer,
I was hoping you would choose the earliest date I listed. I am looking forward to seeing you as well. If I know you at all by now, you probably bristled at my use of the word “instructions” in my last note. Remember what I said previously about control and trust. This is where I take control.
8:00pm. Next Friday night. The Majestic Hilton hotel. Check this website after 5:00pm that evening and there will be a room number posted. When you arrive at the room at 8:00pm sharp, you will find a blindfold hanging from the doorknob. Put it over your lovely eyes and knock twice. I will handle everything else.
If you object to my “instructions” then this shall be our last communication and I’m truly sorry your journey ended even before it began. If you choose to embrace your sense of adventure, I will be there eagerly anticipating your knock.
Mark
And that is how I found myself standing in a virtual stranger’s hotel room, blindfolded, half-naked and more than a little aroused. For once in my life I had surrendered control and had no idea what to expect next. I never felt more alive.
Volume Two: Alphabetical Assignation
Prologue
Tonight was the night we selected together. It was either going to be the first step on an exciting journey or a big mistake. I would know soon enough.
As Friday afternoon slipped by, my technical staff started disappearing for the weekend. My assistant Melissa poked her head around my office door around 4:00pm and started some not so gentle probing about my weekend plans. Perhaps she was more perceptive than I had been giving her credit for. So far she had resisted her natural impulse to inquire further about the roses Mark sent two weeks ago even though they were still prominently displayed on my desk.
To be fair, she was probably a little puzzled by my reluctance to share details with her as I had previously been quite open with information about my dating life, or lack thereof.
The whole office knew about the divorce and my husband leaving me. If I had taken a poll, the majority of them probably thought it was justified due to my fairly stern manner around the office. They definitely did not know what to make of my cheery manner the past week or so. The anticipation I felt about tonight seemed to be manifesting itself in a nervous laugh and an automatic smile.
As 5:00pm finally arrived, I once again turned to the website Mark had set up for this most unusual venture. The old fashioned scroll I was so used to by now filled the screen.
8:00pm. The Majestic Hilton.
Room 1147.
Put on the blindfold and knock twice.
Take a deep breath and relax.
Trust me.
As I drove home I thought about what I was going to wear tonight, only for the hundredth time this week. I had a favorite little black dress that fit my curves so well it was probably illegal in several Bible belt states. I was thinking that perhaps I would wear the emerald green lace bra and matching sheer panties to bring out the green in my eyes.
I took a long hot shower and as I lathered myself I could not help but think about Mark’s hands and eyes travelling down those same curves later that evening. My nipples took immediate notice of that thought as they stood at attention despite the hot water cascading over me.
After quickly toweling off, I stood for a moment in front of my full length dressing mirror and examined myself critically. Standing about five foot seven in my bare feet, I thought I didn’t look too bad for being almost forty years old. I definitely was no longer the teenager that could bounce quarters off her taut stomach during all those bikini summers long ago, but I had not completely let myself go either. My long legs were in pretty good shape from years of early morning power walks around our neighborhood. My breasts were still one of my favorite features even if they weren’t quite as perky and proud as they once were. I suppose if I were to be completely honest there was a slight spread around the mid-section that could be directly attributed to my poor eating habits since the divorce. Burying myself in my work, I had taken to working late and grabbing something quick to eat on my way home. My selections were typically ones of expediency instead of healthy choices. Even though I was an excellent cook, I really had trouble generating any enthusiasm towards cooking for one.
As I pulled on the sheer green panties in front of the mirror, I noticed a few gray strands intruding on my shoulder length reddish-brown hair. They were easily dispatched by a few well placed plucks with the tweezers. Wandering back into the bathroom, I wondered idly whether Mark would prefer my hair up or down. After several variations with clips and hair bands, I finally decided to leave it down, hoping in the back of my mind perhaps to feel his fingers run through it. Applying some light makeup and a candy apple red lipstick, it occurred to me that I was spending a long time covering up that which was likely to be completely exposed before the evening was over. The black silk dress I slipped into somehow left me feeling more naked than before putting it on. It clung to my curves and left little to the imagination.
Gathering my keys and my courage, I slipped into the black peep-toes that matched my dress perfectly. My toes peeked out from the pumps and mirrored the brightness of my lipstick. Checking out the total effect in the hallway mirror, I smiled as I headed for the garage. I sat behind the wheel for a moment before starting the car. All dressed up or not, part of me wanted to flee back into the house and the comfort of my normal routine.
Mark would be the first man other than my ex-husband and my gynecologist to see me naked in close to two decades. I was equal parts aroused and terrified at the thought. What if he did not like what he saw when the clothes came off? Was I really ready to share my body with someone I barely knew?
1
Arriving at the hotel a few minutes before 8:00pm, I quickly checked my makeup in the rearview mirror before getting out of the car. I barely recognized the eyes looking back at me. Slightly dilated and wild, they seemed to be projecting my inner anxiety and excitement.
Walking straight through the elegant lobby towards the bank of elevators, I smiled as I turned a few heads, including the stuffy looking clerk behind the front desk. Taking the elevator up to the eleventh floor, I walked down the hall and found room 1147 at the very end.
There was a black lace blindfold hanging off the doorknob. I must admit that right up until that very moment this had all seemed like more fantasy than reality. I stood there for a moment holding the blindfold in my hands. There was a small part of me that still felt like I should simply turn around and walk away. There was a much bigger part of me that was ready for something new and different in my life.
I slipped the blindfold over my eyes, took a deep breath and knocked twice on the door. I heard it open and Mark’s warm voice filled my ears. “Come in, Summer. I am so happy you chose to join me tonight.” He led me into the center of the room and stopped. “If you would please, just stand there for a moment while I feast my eyes. You look absolutely stunning! That lovely dress is going to look very stylish on the floor next to the bed.”
I never heard him move, but I could feel him behind me now. As he nuzzled the side of my neck, he pressed himself lightly against me. How on earth could he know that my neck was one of my weak spots? Whatever reservations I once had at giving up control to this stranger disappeared as my nipples did their best to rip through the lace bra and silk dress.
“I must confess that you are wearing much more at the moment than I am,” he said. “Allow me to even the playing field.” As he slowly unzipped my dress, he followed the descending zipper with his soft lips and tongue. He reached up and tugged gently and the dress pooled at my feet.
My hesitancy at Mark seeing me naked disappeared completely as I heard him gasp softly when my dress hit the floor. I stood a little straighter and pushed my chest out a little more aggressively as I felt his gaze travel over me.
Pressing his body back up against mine, I could feel his hardness insistent and strong along my mostly naked ass. His hot breath warmed my ear as he spoke softly. “We have talked at length about control and trust, so I thought it was important to let you know what you might be expecting this evening. Our journey to this point has been a literary dance of flirtation and allusion. Now things are about to get very real.” Mark alternated between slowly grinding his hard cock against me as he spoke and pulling away, causing me to unconsciously push my hips back, seeking that physical connection once again.
“Your intelligence and literary verve have lent themselves to an idea for how to expand your sexual horizons while giving us both a great deal of pleasure. In that vein I will say that you have arrived here tonight for what I will call an alphabetical assignation. Over the next year, if you choose to continue on our journey together, you and I will explore the sexual alphabet together. Every two weeks, assuming you do not tire of me, we will meet in this very room for another lesson. Before you laugh or scoff at my idea, I want you to feel something.”
Mark guided my hand to feel his hardness. My pulse, already racing, accelerated even more as I felt his length through his silk boxer shorts. Honestly not having that much experience I could not tell you if he was larger than average, but compared to my ex-husband, he felt enormous.
“Remember your safe word and what I said about not using it lightly. Now with your lovely hand feeling the excitement you are generating in me, I want you to consider the obvious choice of what the ‘A’ in our alphabetical adventure might stand for. You are going to come for me several times tonight, but in the meantime I want you to think about how it is going to feel to have my hard cock buried in your lovely ass.”
2
While I had very little sexual experience with my ex-husband, we had indeed tried anal sex. Once. My discomfort level made it an unpleasant experience for both of us. Hearing Mark indicate his intent to bury the telephone pole in his pants in my rear entrance threw a bit of a damper on my revving motor.
I considered for a moment using
the safe word or simply removing the blindfold and walking away. Even now, more than a year later, I wonder how different life might be if I had done so. I think I figured it would be easy enough to put a stop to things later if he was still insistent on playing with my exit-only passage.
Mark reached around me and slid his hands slowly from my hips up to my breasts. He cupped them softly as he pulled me back into contact with his hard shaft. Lightly kissing the side of my neck and shoulder, he slowly and gently rolled my sensitive nipples between his strong fingers, immediately refueling my desire. Spinning me around, he kissed me softly on the lips and slowly pushed his hard cock up against my moistening panties. I gasped softly as his length grazed across my throbbing clit.
“I want to take this blindfold off so I can see you,” I said.
“Not quite yet Summer. I would like you to experience for a while what it is like to have no idea what is coming next. Control and trust. Trust me a little longer if you would. I have your best interests at heart, I promise. Then again, with that blindfold on, the room could be full of horny little Japanese businessmen with digital cameras and you’d never know.”
Even though I could hear the humor in the timbre of his voice, his words gave me a momentary pause. I did not know for certain if Mark was the only other person in the room with me. Feeling totally out of touch with my own personality, my pulsing clit seemed to be running the show. If I were a man it might have been said that perhaps I was thinking with the wrong head. Since my nipples were hard enough to cut glass and I could smell my own arousal, perhaps the saying applied nonetheless.
The edge of the bed hit the back of my knees as Mark gently guided me over to it. He reached down and placed both my hands on his erect cock. Somewhere between his last kiss and the edge of the bed he had lost the boxer shorts. His penis felt silky soft, yet hard as oak under my hands. Mark reached around me and unhooked my lace bra, freeing my breasts to his hungry gaze, and then his hungrier lips as his tongue danced around my swollen nipple.
What to Read After FSOG: The Gemstone Collection (WTRAFSOG Book 7) Page 187
