Valentimes: Worst and Best of Times

I like things precise.

I like things defined, quantifiable and concise. The digital spreadsheet in my opinion is the greatest invention since the mechanical pencil or maybe even the printed Gregorian calendar. I work hard to create and keep an orderly world, therefore I don't like surprises. Surprises are just messes that have to be cleaned up.

I want to identify exactly where something begins and I like to put a fine point on the chart to show where it ends. I like to live between well defined boundaries; no shadows, no gray areas and no indefinite starts or finishes. A clear, well defined, intentional life is a life well lived.

I was feeling good about my scheduled time with Cynthia. Since I do not like surprises, I had my personal affairs organized and arranged on my spreadsheet. Planning ahead, I had cleared it with my supervisor; I would come into work early, thus allowing me to leave early in order to effectively manage a few errands in the late afternoon. I cleaned off my desk, leaving it neat and orderly. I stopped to check in with the boss to let him know I was leaving early, as we had agreed. He waved me on down the corridor after saying with a smile, "Be careful out there, it's Friday the 13th." I believe he meant it all in good humor, but I found it irritating that a technologically advanced society would still pander to notions of certain unlucky days. It was illogical to think that Friday the 13th was anything but the day before Saturday, the 14th of February. Tomorrow would be Valentine's Day; it was designated as such on my calendar.

I put no stock in the belief of an unlucky Friday the 13^th; the day carried no special import. Not so for February 14^th. It was evident to me that there were certain societal expectations placed upon my sex for the following day, Valentine's Day. These expectations were mostly known quantities that could be anticipated and planned for appropriately. The jeweler was my first planned stop; Cynthia had hinted - or more honestly put, Cynthia had selected a diamond pendant that I was to purchase for her Valentine's Day gift. Only she wanted the center gemstone to be larger than the one initially mounted and she also insisted on a higher quality diamond before she would be seen wearing it. The jeweler's modifications would take some time, but with an upfront payment, the order was expedited and would be ready for pick up at 4:40 PM this afternoon. The second cell on my spreadsheet schedule was the florist's shop. I dislike surprises, so in order to make sure there were no glitches and to avoid tomorrow's Valentine's Day rush; I was smart and had scheduled to pick up my pre-ordered bouquet of roses and baby's breath at 5:30 PM this evening. I was assured that the flowers would look marvelous tomorrow if I kept them in my fridge overnight. Prudent planning predicated that I would call Chez Seine after my stop at the florist's to confirm tomorrow evening's reservations for two. I had already paid in full for the Valentine's Day 'Lovers Special', a romantic table with a view of the river. I needed to double check on my reservation; I didn't want any ugly surprises, I'd hate to disappoint Cynthia. I walked out from my office building confident in my belief that my plans were orderly, in place and ready to be executed.

For my pre-Valentines errands I had scouted a more circuitous route that would take me through an older residential neighborhood, longer by the odometer, but I calculated I could shave off several minutes of valuable time by skirting the Friday afternoon traffic which was sure to be backed up on the main arterial boulevards. I knew traffic would be even slower with the mist and light rain that had moved in with the afternoon cold front, dropping temperatures down around freezing. I felt confident in my planning and my time management skills.

So. Where did all of this begin? I hate to admit that I find it difficult to pinpoint exactly where and when this messy, indefinite, discombobulated and confusing set of events started. I have to believe that I am to blame, at least in part, for the disastrous chain of events. I should have been focused on the task at hand, as I usually am. I blame myself for thinking ahead and losing crucial concentration. I blame myself for allowing my mind to wander as I considered what Cynthia will expect from me after our appointed Valentines dinner. I knew from past unpleasant experiences that Cynthia had definite likes and dislikes when it came to -- shall I say, intimate moments.

I admired Cynthia, because unlike most women, she was direct and I could quickly categorize what she liked and what she did not like about me or my habits. Just before the disaster struck, my mind was focused on anticipating possible events following our dinner date at Chez Seine. I could expect Cynthia to direct me on the drive back to her place; if I was told to pull up to the curb to let her out, this meant that she did not wish to see me anymore that evening. If I was told to park in the visitor's lot, then I could expect that she would invite me up to her place. If I was instructed to follow her to her door, then I could expect that she would allow me to have some intimate time with her. I was thinking ahead about which choice she would make for us, therefore I was not thinking about the task at hand. It was my mistake.

Cynthia's usual modus operandi was to ask me to pour each of us a glass of wine. We would sip wine and talk as she kicked off her heels and if she reached across the table to touch my hand, then that was her signal that it was appropriate for me to take the evening further. Cynthia had set up this signal (and several others) early on in our relationship and I had created an encrypted spreadsheet to document Cynthia's signals and her preferred responses on my part. I studied and memorized the list of interpersonal signals which Cynthia had provided; this study reference made it easier for me to enjoy a smooth relationship with her. I was reviewing the list in my mind right before the disaster.

I admit that I probably lost focus on driving and my errands as I was thinking about tomorrow evening and how it might play out if Cynthia signaled me with a touch of her hand. Cynthia had informed me that if she touched my hand, then it was my job go hand wash and dry our wine glasses as she excused herself to her bedroom. Once the stemware was returned to the cabinet, I was expected to come find her on the bed. Cynthia insisted that I always start our intimate time by rubbing her shoulders and back. I was permitted during her back massage to begin to undo her outer clothing and I was encouraged at this time to kiss and caress her exposed skin. Cynthia had smooth skin, pure and milky, which contrasted to her short cropped black hair, she reminded me of an artistic black and white portrait photo in the flesh. She liked the skin on her back scratched until it was red. Sometimes she would tell me that she liked what I was doing, but most of the time I had to guess by watching her reaction in her green eyes. Cynthia would tell me when I could unclasp her bra to deliver the longer, scratching strokes down her back. If I was permitted to unhook her bra; it was a sign that we had reached a point in our relational flow chart where there was a high percentage chance that it was going to be a good evening. It meant that I had managed to avoid any of Cynthia's criticism of my approach. I got excited when Cynthia's entire bare back was exposed and I slipped the straps off of each shoulder and gently pulled the entire garment out from under her. My task was to properly fold her bra and place it on the chair next to her bed and then return my attention to her skin until Cynthia was satisfied with my efforts.

Right before the disaster, I must have been thinking about the moment when Cynthia would roll onto her side exposing one of her breasts to me, an indication that I was to now pay attention to her chest. This signal of Cynthia's produces a pavlovian response in my penis; I always stiffened at the sight of the subtle curve of her breasts, small and white, capped with pert, hard nipples that reminded me of ripe, flavorful raspberries. I imagined raspberries sitting atop a scoop of French vanilla ice cream. I would lie next to Cynthia as she held the back of my head and pulled me to her chest. I licked and flicked her raspberry, softly at first and then paced myself to work her harder with my stiff tongue. I would envelope her plumped up nipple with my lips, holding it firm between my moist lips while I darted my tongue out to circle the tip of her nip. This was how Cynthia had diagramed for me how she wanted me to treat her titties. There was some free styling on my part, but I liked having an orderly progression established within the framework of our relationship. Besides, it worked best this way to ensure Cynthia was pleased with my efforts. Cynthia would shift to allow me to switch attention to her other nipple as she used sweet humming sounds to indicate approval of my approach. At times my tongue would get exhausted from the work I was performing on Cynthia's breasts, but overall, I was privileged to be allowed to have access to the sweet scoops of my lady's fair skin.

I usually worked long and hard while Cynthia enjoyed the handiwork of my tongue and the foreplay of my fingers stroking her ribs. At some point, it appears that a woman knows when she has reached pleasure saturation from nipple play. When Cynthia comes to this saturation point, she would roll flat on her back and indicate to me that it is time to remove her skirt or pants. I will undo the buttons or zippers on her always fashionable apparel, slide the fabric off of her hips and properly fold the clothing and place it neatly over the chair holding her bra. I will never again make the mistake of acting so inappropriate as to begin to remove her panties. I started to fully undress Cynthia once and only once; only to have the evening end abruptly for some reason. I guess I crossed some invisible line in the universe, at least invisible or unknown to me. Cynthia made it clear that it's a woman's prerogative to as to when a man can see her nude lady parts. I won't make that mistake with Cynthia again; she'll make damn sure of that.

During our intimate times, I discovered a secret signal, one that I had not disclosed to Cynthia. After I undress her down to her panties, I would take a peek right between her legs to look and see if and how large of a wet patch I saw on her panties. This is my secret gauge as to how sexually excited Cynthia might be. Albeit, it is a qualitative assessment, not a quantitative one; but it does offer a hint as to what Cynthia will want next. I've noticed a correlation that when her wet spot appears to be particularly sodden with her vaginal lubricant, she will usually opt to select a vibrating device from her treasure box and begin to apply the vibrations to her clitoris. Sometimes while still wearing her panties and sometimes after she has removed them. Otherwise, if her panties are not displaying a large damp spot, she will have me move between her spread legs and provide some tongue action to her labia and clitoris after she has tossed off her undies.

If Cynthia has achieved sufficient arousal and has tipped her mood by the larger volume of sex fluid she has unconsciously generated, then I know that she will want to personally handle her own climax without the distraction of a boy. She will have me hand her treasure box to her from under the bed and she will look over her options. Sometimes she will draw a small bottle of lotion out of her box and hand it to me. If this happens, I understand that I am to pour some of the lubricating oil into my palm, let it warm there for a moment and then begin to apply the lotion of emotion to her private parts. For Cynthia's taste, I usually fail to get it warm enough before applying it, but after a quick inhalation and perhaps a scolding, "It's still too cold!" she will let me go ahead and pet her warm and engorged labia with my slippery fingers. Since, apparently I now meet her approval. Her green eyes are often closed, but I will watch her face as I use two fingers to part her outer labia and move a single finger to make little rotations on her clitoris. This light touch never fails to bring a deep moan from her. Cynthia will let me finger play with her sweet spot for some undesignated time until she will wave me off.

At this point in our scripted intimate time, she has already placed beside her pillow her selected vibrating device and on occasion, a second toy that she will use to push into herself while stimulating her clitoris. I enjoy watching her growing arousal as she holds her vibrator tight to her point of pleasure. I watch her belly muscles flex as her orgasm builds. I like to listen to the moans and whimpers she emits as she moves her vibrator to another spot, only to make her draw her legs up with bent knees as she begins to thrust her pelvis into the hand holding her device. As her sex sounds go from quick burst of punctuated vocalization of her growing pleasure to long, drawn out moans rising to the level of foggy screams. As I listen, I think that if I recorded Cynthia's ecstasy and played it back, the short moans and long screams could be converted into dots and dashes, Morse code, and thus translated into alphabetic characters. Pretty cool idea, Cynthia's personal sex code decoded.

As the longer moans turn to screams, she breaks into a damp perspiration on her brow and neck. The orgasmic waves sweep over Cynthia as I observe her thrash about on her back, her pale skin brightens to a deep red flush as her excitement mounts, making her look like some exotic tropical bird. Cynthia seems to lose all interest in me or even acknowledge my presence next to her while she is concentrating on her waves of electric heat sweeping through her insides. I enjoy that fact that Cynthia allows me to view her orgasmic ecstasy.

During the times when Cynthia is in the mood to pleasure herself, she has told me that she will let me masturbate while I watch her work her sensitive lady parts to orgasm. I am aroused by the sight of her heaving breast, her sex sounds, panting breaths and even the earthy smell of female sexual arousal. I use some of the oil from the small bottle out of her treasure box and slather my stiffened dick and stroke myself to keep pace with her mounting orgasm. I often have to slow my strokes as I watch Cynthia writhe. I listen to her as I try to time her orgasmic moment to my ejaculation making it coincide with her climax. It is not always easy to judge her progress. At times Cynthia builds up in a geometric progression, higher and higher with each minute until I witness an ecstatic convulsion with shaking legs and breathless gasping. Other times, I watch and wait and am mystified as to what this woman is experiencing. Perhaps there were a few subtle sounds and physical manifestations, but she is done before I even knew she got started. I find Cynthia's fluctuations and unpredictability hard to anticipate, which at times put some stress in our otherwise well delineated relationship.

Cynthia says she is fine with letting me find satisfaction as I watch her, but that she does not want to have to clean up any of my mess. I was informed that I was not to let any sperm get on the fabric. Cynthia's solution was to provide some old towels for me to ejaculate on, but if I did, it was my responsibility to wash them and return them to her freshly laundered.

I find myself a bit more excited when I peek at Cynthia's panties and see that she has not heavily soaked them in her self-generated feminine lubricant. This sign will often indicate that she will remove her panties, adjust herself on a stack of pillows and direct me to come between her spread open legs. She will use her hands to part her labia and show me her clitoris, hidden within her pink folds. I have a job to do, that is to get her further sexually excited, and if I do a good job, I will be permitted to have real sex with Cynthia.

Beginning down near her bottom, I let my tongue travel up one side of her cleft, licking methodically up toward her fascinating folds of pink flesh. I do not touch my tongue to her little bud, but I drop back down and travel back up; making sure I keep to the external labia. Cynthia may be impatient with me at this point, but I feel I have some control in this situation, so I pause after a couple of repeated tongue teases. I return to her slickened vulva with an out stretched tongue that I place dead center in her vagina. My tongue is broad and flat as it licks a wide swath across all of Cynthia's most secret and sensitive places. Cynthia says no words as I make another pass over her as she holds the sides of my head in a tight grip as I rise toward her excited nub. When my tongue makes contact with her clitoris, her whole being jolts as if she'd touched a live 220 volt electric wire. She lets out a wolf sound as she clenches her jaw and lets the reverberations rattle around her loins. I keep playing with her folds and the edge of her void with tongue and lips, making a few moderations to my maneuvers, but all the while I persevere to keep up a good licking and sucking.

I have learned over time to taste her juices as they flow from within her and over my taste buds. Cynthia's secretions change as her arousal grows. After I have engaged Cynthia in oral sex for a while, I can sense a thicker viscosity and a taste that reminds me of sweet cedar. I know Cynthia is at a stage of heightened arousal when I taste her like this. For a finishing touch, I insert a finger inside her and find the roof of her vagina where it feels like the rugose hull of a soft walnut. I rub this spot and listen as her breath becomes labored, her pelvic muscles begin to clench and she throws her hands to cover her face as she lets out bursts of deep moans as she squirms in reaction to my touch. I am now the one in control, because I don't think Cynthia has much capacity to voice a clear command to me when she is like this.

Once fully aroused by tongue and finger play, Cynthia will now allow my cock to enter her -- after I place a condom over my shaft. Cynthia says she likes to be fucked on her back the best, but sometimes, it is all right if I put her on her knees on the edge of the bed and come at her from the backside. The mixing of my spit with her natural juices has made her pussy sloppy wet. I push her legs apart and ease myself between them, stiff with excitement. I roll my hips forward, slow for the first two or three strokes to make sure my rubber is properly slickened. I then cut loose and hump Cynthia hard and fast. If she's in her preferred position on her back, her legs usually come up to wrap around the small of my back as my thrusting makes her raspberry nipples jiggle. I will bend down to lick her nipples as I keep pounding her. Cynthia seems to like the simultaneous stimulation of her titties and pussy. When both titties and her pussy are in play, I get the most enthusiastic screams out of her between panting breaths. I think she can sense when my loins are about to erupt, her response is to arch her pussy up to meet my rapid thrusts as I come to a climax. Cynthia will relax for me at this point as I withdraw and hand her a towel to clean up her wetness. It is my responsibility to dispose of the condom and make sure that no messy male fluids leak out onto the bedding, making a nasty stain.

It is difficult for me to remember exactly what thoughts of Cynthia were in my mind at the instant of the disaster. But I blame myself for letting those ideas travel around in my head and obscured my proper perception of my environment.

From my right breast pocket my phone gave a sharp ping; all incoming text messages of course sound the same, but all the same, I could not help but think that this sharp, pin-prick, insistent ping, sounded like one of Cynthia's summons. Cynthia is all business. She likes precision and defined parameters, which is why I thought we were a good match. If Cynthia's personality could be converted to a mechanical tone, I believe Cynthia would be personified as a sharp PING! Short and to the point. Against my better judgment, I shifted my gaze down to extract the phone from my jacket to see who had texted me. It was completely illogical on my part, but I knew the text was from Cynthia without looking. If I need to demarcate the beginning, and I think I do, I would have to place the inflection point of my life's changed trajectory at 4:28 PM. I have saved that text from Cynthia, perhaps from some illogical emotional weakness or a perverse need to mark the manifestation of a failed relationship.