Diane  

WolfieInApt26 69M
4 posts
11/18/2005 10:28 am

Last Read:
7/16/2009 3:03 pm

Diane


Note: There are a few "times" (i.e., hhmm) that appear odd. They have semicolons between the hours and minutes instead of colons otherwise AdultFriendFinder converts them to smileys.

As the streets moved out to the river from the center of the city the buildings became smaller and older. Here, where the end of 57th street meets Second Avenue, almost all the buildings were three or four stories and narrow. Rental space was expensive and almost every floor was occupied by up-scale boutiques, decorator lighting stores and pricey specialty shops. Bustling during the day, late at night the pristine scene was interrupted only by an infrequent cross-town bus or an occasional person walking to or from Second Avenue. At midnight the store interiors and recessed doorways went dark. Street lamps illuminated some store windows, sent shadows of naked branches across others, and left the rest in the city's darkness. It was a chilly night made worse by a wind coming off the river unimpeded by buildings between there and the water. This block led to the stop where I would often wait with Diane for the bus that would take her over the bridge and home. She would always go home when we were out together on a weekday and today was Wednesday.

Curfew for our friends on a weekday was usually midnight but Diane and I sometimes continued on our own for a couple or more additional hours. There were a few times we partied until five or six in the morning giving us just enough time to get home, shower, change clothes, and get to work. Staying the night at my place was not practical because she didn't keep a change of business clothes there and showing up at work wearing the same outfit worn yesterday was equivalent to having a dozen red roses delivered to your office: both broadcast you got laid last night. Receiving roses says you were especially pleasing. Coming to work in the same outfit says you were out last night whoring. Although there's nothing wrong with a woman doing either it's usually not good office etiquette to advertise. I'd rather she went home anyway. Diane was easier to deal with on the weekend but even then she's gone home early in the morning in a taxi. Keeping some of her clothes at my apartment smacked too much of commitment. I wasn't ready now nor did I think I would ever be ready to see her exclusively. Unfortunately, that's exactly the idea I've lead her to believe and there is almost nothing Diane wouldn't do to keep it going.

Our evenings together often, but not always, started the same way: we would meet at a hotel bar, have a drink or two, then move on to a club or restaurant where there was food and drink. If there was also dancing, that was a huge plus. Diane knew many of the snazzy hotels with bars so she was the one who usually suggested one we hadn't been to together.

I got hung up at the office with my manager who had become antsy about my largest project and called me to his office so he could micromanage the parts that were going fine without him. He was actually one of the better managers I've worked under. When he needed to, without hesitation, he would get the right person on the phone and set things up for me to follow through on or resolve an issue that was holding me back. He was authoritative but always pleasant with me and we got along well. There was no doubt in my mind he valued my talents highly because of the double-digit raises and other perks. So while I thought I might be able to leave around 6;00 PM it was now closer to 7;00 and we hadn't yet begun to slow down. I excused myself for a hygiene break and called Diane on her cell, "I'll be there as soon as I can," I told her. I would have liked to tell her not to drink too much but I couldn't think of any way to phrase that advice without appearing judgmental. When I got back to my manager's office he had taken out a couple of bottles of single malt scotch he kept in the credenza behind his desk. He would invite those in the meeting to have a taste whenever a meeting went on until 7;00 PM or later. Being a single malt aficionado myself and wanting to keep the golden goose happy I would make sure the scotch supply never wanted for a new label. Breaking out the scotch was a signal that the meeting was ending. It didn't take long on an empty stomach for us to feel the scotch and the meeting to become less productive until we reached a point where we were talking more about the Scottish highlands than whatever the meeting was about.

Diane was seated at the bar when I finally got there so I walked up behind her, put my arms around her waist, and kissed her on the neck. She swiveled around, said, "Hi," and kissed me on the ear as I was sitting down on the adjacent stool. I didn't like when she kissed my ear because she always planted it in the center causing my eardrum to pop and a distasteful ringing lasting several minutes. I'd tell her not to do it but she thought it was cute and often smiled at my protestations. I didn't say anything to her this time because I should have known better and worn ear protection. Diane could be hard on a guy.

She had been waiting a while for me and was finishing off her second drink so she ordered another. The scotch I had at the office added up to about one drink so I ordered another also. Diane told me what transpired in her office today including the family members, medical histories, and attire of everyone involved. She laughed when she told some stories and took a serious tone telling others which helped me know when to smile and when to shake my head--getting a word in edgewise wasn't an option even if I had wanted to. I didn't know or care about the people, wasn't interested in what tragic illness had befallen them or one of their family, and had no curiosity what the gay mailroom guy wore. There would be plenty of time later to broaden the scope of our conversation but for now all I wanted to do was sip my scotch. When it was time to go all I had to do was interrupt her and say, "We should leave now." Diane would stop talking in mid-sentence and reply, "Oh, okay," and we'd be off.

Diane was really a sweet kid and we danced well together. Play almost any music that lent itself to partner dancing and we could put on a show. Finding a place to dance the quicker Latin dances was not difficult but locating a club that played slower music like Rumba, Bolero, or Tango was not so easy. Argentine Tango was the exception. With a revival of the dance brought on by Hollywood and Broadway there were several exclusively Argentine Tango places, unfortunately, Diane didn't dance Tango Argentine, as it's sometimes called. She couldn't dance other dances that I could but that didn't dissuade her from asking me to dance them with her anyway. "Oh, come on. How hard could it be? You lead, I'll follow," Diane would plead which was strange because she knew that the dances she executed so very well she hadn't learned overnight. Of the dances we both knew Diane was more advanced than I but not so much that she couldn't back-lead me into the steps I didn't know.

We knew all the dance studios and when they had their weekly group practice sessions: we could sometimes get our dance fix by crashing them. Crashing wasn't an ideal solution because there was usually no alcohol served and since we were both good dancers we stood out, were found out, and asked to leave. There were some studios we never bothered stopping by because they trained mostly women of means for International style competition. We were totally out of our league at these places that cater mostly to obnoxious Russian bitches. Besides, there was no food at studio parties except for pretzels and potato chips that sometimes had to keep us until ten o'clock or so.

Although dancing was a much-desired part of our evening there were some times it was just not possible and this was one of those nights. We stayed at the hotel bar for another hour then left to meet up with some of our friends, two couples and a single woman, at an Irish bar and grill. One couple, Edie and Ralph, ordered full meals. They always did whenever we got together but Edie would invariably excuse herself for about a half hour when she had finished eating. Edie was tall, thin, had spent way too much time in the sun, and from her behavior after meals and a gray tinge to her teeth, we all believed she was bulimic. Although they were close to a generation older than Diane, and me we had stimulating, peer-like conversations. They were both somehow associated with real estate. Theresa and Chris, the other couple, worked for an investment bank. While the others talked above the din of the bar, Chris and I laughed at his latest batch of political jokes. The lone single woman, Tatiana, was a married Russian lady whose older husband hardly went any where with her. I never quite understood what she was talking about, partly because of her accent but mostly because she was a bit of a loon. Everyone knew Diane years longer than I did. Other than Edie and Ralph who ate proper meals, we chowed down on an assortment of fried food. Without fail, every time we'd place our order Diane would say, "Everything is better when it's fried." And we drank. Theresa and Chris stuck to beer and ale and Tatiana drank straight Vodka exclusively. Edie and Ralph drank martinis, before and after Edie spent her usual half hour in the ladies room. I stayed with my scotch and began to pace myself as soon as I began to loose feeling in my fingertips. As was her custom Diane upgraded her libation to Hennessy, Courvoisier, Remy, or occasionally B&B. At eighteen dollars a drink I was lucky her taste for distilled spirits was self-financed.

We were there for at least three hours. Somewhere during that time most of the other customers left so when we got up to dance to the piped-in music no one objected even though the owner could have been fined for not having a cabaret license. We all danced with each other except for Tatiana who often danced by herself because everything she danced was Cossack-like regardless of what was playing. Tatiana was a group project since she tended to do table-dance solos. She wasn't a looker but I thought she wasn't too hard on the eyes so it wasn't difficult to keep an eye on her especially with the view I had when she was on a table and I was seated. As the evening went on she became bolder and began pressing herself against whomever she danced with. I didn't mind but Diane was not the only one who did.

I had no more time for Tatiana. Diane was off balance, missing steps and bumping into tables. I interrupted she and Ralph and said to her sternly, "Diane, you're not able to dance anymore. Go sit down. I'll get you some coffee." She sloughed off my concern slightly slurring, "Oh no, I'm fine. I don't need any coffee." But I told her, "Dancing time is over. Go sit down." Diane pouted but did as she was told. Sulking, she drank the coffee; unfortunately, she also found it necessary to finish off a double cognac she had ordered only minutes earlier. Everyone knew Diane was tipsy: it wasn't the first time. It was time to leave and it was up to me to see she got home. Goodbyes and kisses exchanged, Theresa and Chris poured Tatiana in a cab.

I put my arm around Diane's waist more to hold her steady than to show affection. She had her arm around my waist but I think it was more affection than to steady her. With our arms around each other's waist walking was more difficult than it had to be. I had had too much scotch to drive but I still felt safe walking Diane to her bus stop. Muggers look for drunken targets but I didn't think I looked drunk. We were soon on the last block of 57th street. Diane wasn't that far gone that she didn't know where she was and realized that she would soon be on a bus home and if she wanted to end the evening on a better note she would have to do something soon. As we came upon an antiques store she pulled me into its recessed entry, threw her arms around me, and planted one on my lips. She was in her aggressive mode and she drove her tongue in my mouth. At the same time she opened the fur coat she had borrowed from her mother, took hold of my left hand, and placed it firmly on one of her breasts. With her other hand she unbuttoned her blouse almost to her waist, slipped the strap of her bra off her shoulder, and freed her breast from its confines.

The same alcohol that made my fingertips numb allowed me to lay aside any thought of consequences and I vigorously returned her tongue's advances while I slipped the other bra strap down her arm. Without unhooking her bra I pulled it down enough to let both breasts free and fondled them a bit roughly. Diane responded by pulling my head to her breasts. I worked her nipples with my mouth while my hands found their way under her skirt and up her legs. It was very exciting to see her erect nipples while I lifted her skirt and felt the inside of her thighs. The cold wind blew into the doorway and I slipped both hands into her panties from behind and pulled her into me as I squeezed her cheeks.

There are city ordinances against such public displays but we didn't care until a car's headlights illuminated the doorway and the two young men in the car cheered me on yelling, "Go for it!" They drove off and I looked around to see if there were any other observers. There were none so I kept her mouth and tongue occupied while I started to pull her panties down. The waistband of her skirt provided a little resistance but I was able to get her panties down around her legs easily, slid my right hand between her legs and fondled her mons pub with my fingers. Diane took over from me and used both hands to pull her panties down the rest of the way and stepped out of them while I lifted her skirt and watched with delight. All this time her fur coat shielded us from the wind but was not as effective at keeping prying eyes at bay.

Our mouths separated and she threw her head back as she wrapped one leg around me. I licked one finger and slipped it in and out of her while I wondered just how far we would go in this doorway. Diane showed no signs of flagging. Just then I was startled to hear someone quite close ask, "Need a hand"? It was the two guys that had passed by only minutes before. They had driven around the block and parked while I had my face buried in Diane's fur. I hesitated: I couldn't decide how to respond. Before I could say anything Diane looked at them, said nothing but opened her coat as an invitation. Automatically, I spit out, "No," but Diane, with a defiant tone, countered with, "Come on, it's fine." Although she was eager to experience new things sexual, it was the alcohol that agreed to their proposition.

The other guy, not the one that offered a hand, said, "Not here though. Let's see what's around back." He took Diane by the hand and the four of us walked into the alley on the side of the antiques store. Eros must have been having fun with us. What are the odds that the only alley on the block, an alley I had not seen before, was next to the very store where Diane and I were engaged in amorous behavior? At the end of the alley was another wider dead-end alley that ran behind several of the buildings. The only light was from two security lights, one in the alley from the street and the other at the far end of the connecting alley. In back of the buildings were only remnants of any wind out on the street. It was stupid to let myself be lead into such a vulnerable position so I stayed at the juncture of the two alleys to facilitate a run for help should it become necessary. Diane was a few feet away in shadow, her back against the brick wall, under a fire escape. The guy that escorted Diane was between myself and her partially obscuring my vision of what was happening but not enough that I couldn't see he was stoking Diane's hair with one hand while the other was inside her coat. Being preoccupied with what was going on to my right I lost track of where the second guy was until he startled me when he offered me a cigarette. I started smoking in my teens and had quit a couple of years back but this seemed like a good time to resume the habit, at least for tonight. I took the smokes from him and with a flick of my wrist one cigarette rose from the pack--how I was always able to do that I don't know. I put the cigarette in my mouth and leaned over to get a light from him. He smoked one of those light cigarettes that requires you to draw so deeply to get any flavor that you worry about your head caving in. What I wouldn't have given for a Winston.

He lit up and told me his name was Ken and his friend's was Jeff. Both were seniors at City College. They had stopped with nothing particular in mind and my anxiety level went down appreciably when Ken told me, "I'm not too crazy about being back here." "You think I am?" I replied, "She's had too much to drink. I should be getting her home." Ken didn't say anything but the hypocrisy in what I said was palpable.

After sucking on that miserable cigarette for a short time I looked over at Diane: her coat was open; Jeff had pulled it, her blouse and bra down around her arms; in essence she was naked from just above her waist up. Her hand was behind his head bringing their mouths together. Jeff was vigorously fondling her breasts. I got an erection. Burning embers swirled around from my cigarette hitting the ground while I covered the short distance to where they were. "She's cold!" I exclaimed to him but it was Diane who answered after breaking the hold she had on his lips. "I'm fine!" she countered in a way that put me in my place. I watched as their mouths engaged again and his hands moved from her breasts to her ass lifting her skirt high in the back. When I stepped back her coat covered the rear action but left her skirt visible at mid-thigh in front. I enjoyed watching them more than I could admit to myself. Ken walked back and forth, his eyes locked on Diane and his friend except for peering down the side alley at the end of every other trip and the occasional glance my way. I couldn't tell if he was eagerly waiting his turn or wishing Jeff would finish so they both could get out of there. Jeff was now standing slightly to Diane's side with one hand behind her and the other between her legs. Diane's head was tilted slightly back and to one side as she began to swoon. Shadows hid the details until the hand he had behind her had finished unbuttoning and unzipping Diane's skirt and it dropped on the folded cardboard cartons they were standing on. Jeff opened her fur and looked in our direction so we could admire his handiwork. My erection was now uncomfortably hard. My primal brain was exerting influence.

Without thinking twice I said to Jeff, "I want to fuck her, now." He nodded. Jeff wanted her to kneel so he pushed down by her shoulders but she didn't understand. "Kneel down." he said calmly and she did. He unzipped his pants and pulled out his cock in front of her face. This she understood and eagerly took his cock in her mouth. As she gave him head, Jeff held up his index finger to me so I waited impatiently for his lead. He stopped Diane and got down on his knees himself. She leaned forward until she was on all fours and took his cock back in her mouth. Giving head was her favorite sexual activity and neither the cold nor the fact that she had a stranger's cock in her mouth made her any less energetic. Of course the alcohol had a part in numbing the cold and eliminating any inhibitions she may have had. I could read on Jeff's face his appreciation for her fervor. He lifted his chin in a reverse nod signaling an end to the one-minute sign he gave me earlier.

I slipped my hand under her coat and between her legs. She was warm and moist and ready but, although I can't explain why, I needed to feel her more before I took her. Her thighs were ample and I would have to spread her legs before I could get more than a finger inside her. Diane had been hefty, maybe corpulent, but that was in the past. Now she'd be considered Rubenesque. One distressing part of Diane's anatomy were her breasts. I surmise she was actually quite flat-chested but her pubescent pulpitude gave the appearance of a handsome set of tits. In her later life, after she lost a lot of weight, the fatty tits remained without the supporting breast tissue, which gave her tits an unfortunate mushy feel. As I spread her legs apart her rear dropped a few inches and I was able to massage her womanhood inside and out. With my other hand I unbuckled my pants but I needed both hands to unzip and drop my pants and shorts down. So I wouldn't get Diane's juices on my clothes, I wiped my hand on her hip and made a mental note to go back later and clean that up. While I held on to her thighs my cock found the entrance to her vagina and I pushed it in with my hips an inch or two at a time until I was hitting my hips against her rear. But there was still more cock to bury so I pushed down on her rear which moved her knees farther apart on our cardboard love nest. Diane made a muffled noise. I suppose her legs were now at an uncomfortable angle. Anyway, that did the trick and I was able to get all but a very small length of cock inside.

I started to get my rhythm going but I found it was more physically demanding than I anticipated. Normally I would have pulled her into me as I thrust into her but she was still giving Jeff a blowjob and I couldn't pull her in one direction while her blowjob rhythm dictated she go in the other. From the sounds both of them were making it sounded to me that Jeff was about to come and afterwards my humping rhythm would dominate. Until then I'd just have to draw on my energy reserves.

My face glistened with perspiration and droplets were running down my back when he came in her mouth. Diane coughed once then panted. I started pulling her into me and she joined in by pushing while I pulled. When she had almost caught her breath Diane tried to look behind her to see who was inside her. I don't know that she could see it was me in that alley.

Jeff zipped up his pants and motioned for Ken to come over. He hesitated at first then unzipped his pants and started to get on his knees when Diane stopped him saying, "Wait ... a ... minute," between thrusts. My strokes became faster but shallower as I felt an ejaculation building. One, two, three, four strokes later, I thrust deeply, and came in several waves. I pulled out and cleaned up with my handkerchief. Diane raised her head and looked at Ken: he knew it was his time. So Diane went about giving Ken head. Maybe because he was second or she liked his face or whatever she gave Ken something extra: she stroked his shaft, used her tongue on the head of his cock, and licked his balls. She also asked him to cum in her face which he did but looked uncomfortable doing. Later he said it felt degrading like pissing on someone.

Jeff wasn't done. While Ken was getting his deluxe blowjob Jeff was getting ready to have anal sex with Diane. At first he couldn't find a condom and asked if I had an extra which surprisingly to me I didn't. At last he found where he had stashed his own and ripped one open applying some of the lubricant to his finger. Diane was startled when Jeff put his finger in her anus and let out another muffled sound. I knew she hadn't had anal sex before and I didn't know if she knew what was coming. Jeff worked her anus until two fingers could slide in and out easily. This took a few minutes and gave Ken time to cum in Diane's face. She didn't resist when Jeff positioned his condom covered cock between her cheeks, on her anus, but she began to protest with a shrill sound when he started to penetrate her rectum. Ken, in a spirit of self-preservation, cupped his hand over her mouth and tried to comfort her with, "Shhhsh. It's okay. Shhhsh," but the sound of a muffled scream was still audible to the three of us. Jeff continued fucking her in the ass but before very long he saw she was sobbing and he stopped. However, all this excited me greatly and I became erect again. I had to have her that way. Dropping my pants again and donning a fresh condom I penetrated her again and again while Ken tried to keep her calm. I never came, I simply ran out of steam.

It's strange what comes into a person's mind during sex. While I was pounding Diane's ass an observation came to mind the source of which I've forgotten--it was probably my ex-wife, she had something to say about everything, "Men will put their finger or dick in any hole they find." Aside from being pejorative--another trait of my ex-wife--I think there might be some truth in that statement.

Diane lay on the cardboards. Her arms kept her coat closed around her in an attempt at faux modesty. The "boys" had a smoke while Diane tried to pull herself together. She used the panties she stuffed in her coat to wipe off her face, her rear, and her crotch before tossing them aside. She found her skirt and put it on. She adjusted her bra and blouse and attempted to fix her makeup and hair. The only item of clothing that didn't need fixing were her black shoes. No one offered Diane a cigarette. All four of us walked together out to the street. Ken and Jeff each kissed Diane on the cheek, got in their car and, with a wave goodbye, drove off. I asked Diane if she wanted to take a taxi. She nodded "yes' but followed that with, "But first I want a drink. Will you buy me a drink"? Although it was way past closing time for most bars there was an all-night club two blocks away. We walked there without saying a word to each other. It was no surprise that she ordered a cognac and I scotch. She downed the first and asked that I order her another while she went to the ladies' room. She drank the second drink slowly. I didn't know what to say or what she might say so I thought it best that I just keep quiet. When she had regained some composure she broke the silence and asked me, "Did you have a good time"? She was looking down when she asked me that and I got the feeling it was a serious question and she wanted an honest answer. But it had been a rough night for her and I assumed she was being sarcastic. "Do you think I had a good time"? I asked. Diane answered in one word, "Yes." I followed with, "Would it bother you if I did have a good time tonight"? Her answer surprised me, "No. I hope you enjoyed yourself. I mean it," she said as she raised her head and looked me in the eyes. I confessed, "Actually, I enjoyed it very much." She smiled and said, "Good! Me too. Whatever you want, anytime, anywhere." She gathered up her things, stood, and said, "Now call me a cab, lover." I flagged down a cab but before she got in she kissed me deeply, rubbed my crotch, and whispered, "Call me." As she drove off I realized I let her pay for her own cab. Oh well, I did pay for her two cognacs.

Become a member to create a blog