A Portrait of "Proper Beauty"

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I did attempt to make contact with Allegra a few times over the summer, with no success. Of course I did see her when I was visiting Van, but she acted exactly like she always had, and I tried not to slobber, so I don't think that anyone caught on to the fact that I was enamored with her.

The Van Rensselaers had a pool party at their house on a Friday the day before Van was to go off to college. Even though Allegra was in a conservative one piece suit she still blew my mind, and I avoided making a fool out of myself only because I had mirrored wrap-around sunglasses and loose fitting swim trunks on. Allegra treated me no differently than she treated anyone else; polite and cautiously friendly.

The Sunday morning after the pool party, two days before I was to leave to go to college, I got a call on my cellphone from a number that I didn't recognize. I thought that it probably was a solicitation, but answered it anyway. After I said "Hello" the melodious perfect diction of the voice on the other end quickly identified it as Allegra even if she didn't say "Hello Kevin, this is Mrs. Van Rensselaer. I assume that you're getting ready for college."

"Yes, I am. I'm leaving on Tuesday," I replied, without a stutter.

"Then I'm glad that I called today, Kevin. I have a graduation/off-to-college present for you; I hope that you can stop by about noon so that I can give it to you."

That took me back, and caused my cock to salute. "Sure; you didn't have to get me anything, but I'm sure that I'll appreciate it. Noon it is."

"See you then, out by the pool house," she said before ending the call.

I tried to tamp down my expectations. I didn't know if George or the maid or gardener would be there, or if she ever would have any interest in another sexual interlude with me, but of course in the deep recesses of my mind I was earnestly hoping for another body-joining.

Allegra had on what appeared to be a long pool cover-up when I met her by the pool. She smiled when she greeted me, but no hug. "Come into the pool house; that's where your present is," she grinned.

Sitting on a table in the pool house was a beautifully wrapped large gift. "Please open it now - I want to see if you like it," she said.

I opened it and found a complete high-end artist's kit having every type of paintbrush one could imagine, a pallet, a collapsible easel, a few canvases, and a wide variety of paints, as well as some pieces of equipment that I didn't recognize. It had to have cost at least a few thousand dollars. "Wow," unconsciously came out of my mouth. "This is awesome; thank you so much Mrs. Van Rensselaer!"

"I know from your displays at the art fair and from our discussions that even though you will be studying business you are an aspiring artist in your soul; I hope that this gift gives you pleasure."

"Thank you so much," I repeated. "This is so sophisticated that I don't even know what everything is."

"I used to do a little painting myself," she smiled, "let me explain everything to you."

Allegra told me what the things I didn't recognize were, and explained how they were to be used. Then after her explanations I saw her pull one string on the front of her cover-up, exposing her supreme naked body underneath. When she saw my eyes get wide in a voice even exceptionally sultry for her she asked "Were you expecting something different when I called you, Kevin? Were you hoping for something besides an artist's kit?"

There was very little talking - mostly only her dirty rants and my expressions of wonderment and lust - for the next 110 minutes. This experience was even better than the first one because we primarily used a large, cushioned, deck chair for our activities, which was much more comfortable than the table and basement surroundings during our first liaison. After our passionate hook-ups, as I started to walk away, bowlegged and more sexually fulfilled than any man has a right to be, carrying my heavy artist's kit with both hands, Allegra approached me. She gave me one last passionate kiss that almost touched my soul, and a squeeze of my balls, as she chirped "Remember, our fun little secret," and then dove naked into the pool.

Once again, my mind was fucked up until the serious parts of college orientation, and lacrosse practice, the next Wednesday. I finally got my head out of my ass and made a conscious, mostly successful, attempt to get the Proper Beauty/walking-wet-dream that I call "Mrs. Van Rensselaer" out of my mind.

++++++++

I was enjoying college, starting as an attacker on the lacrosse team, studying in the business school while also taking as many art electives as I could fit into my schedule, and having more than my share of success with the ladies, including a somewhat steady girlfriend, Lizbeth, at the end of my sophomore and start of my junior year. The only bummer was that I had no more liaisons with Allegra. While Van and I were still the best of friends and I saw Allegra during the summer and on holidays, there either wasn't an opportunity for, or she had no interest in, another session of swapping bodily fluids. She still looked as prim, proper, and devastatingly gorgeous, as any other time I had seen her, as I imagined red garters holding up black nylons on her sculptured thighs.

A very fortuitous circumstance arose during lacrosse season my junior year. Van's team was on a road trip, including a game against my college's team on a Saturday at 1 p. m. Since we both played attacker we would not really have much intimate contact during the game, but of course we would be on the field at the same time. Van was the star of his team, and though I was a starter I was probably the fifth or sixth best guy on mine.

George and Allegra didn't have much of a chance to see Van play so they took this game as an opportunity to do that. They hadn't seen me play since High School, so I was psyched for the game - especially because of my interludes with Allegra.

The game was awesome. Van was the leading scorer with six goals and one assist. I played the best game of my life with four goals and three assists, including scoring the game-winning goal with eighteen seconds left, an 11-10 victory for my team.

George and Allegra joined Van and me on the field after the game, and as always Van was a good sport even if disappointed in the outcome. After an exchange of pleasantries and a post-mortem of the game George said "I have to leave on a business trip on a late flight, and I know that Van has to be at his team's hotel by 11 p. m., but maybe Allegra and I can treat you two - and your girlfriend Lizbeth, Kevin - to an early dinner at the Four Seasons where Allegra and I are staying."

I jumped at the chance for many reasons.

The dinner was classy, tasty, and fun. Lizbeth was very impressed with the Van Rensselaers, especially Allegra. Allegra and I acted just like we always did around each other - except when we were one-on-one. She did make a point of telling everyone that she was getting a limo to the airport the next morning.

As we were saying our good-byes, George to take a limo to the airport, and Lizbeth and I to take Van to his team's hotel, Allegra did an unusual thing. She shook my hand goodbye (she was never a hugger in public, except a light hug for Van or George). There was a small piece of paper in her hand. I quickly put it in my pocket. I surreptitiously looked at it before we got into my clunker of a car; it read "Suite 1501."

As Lizbeth and I drove Van to the hotel that his team was staying at before they travelled to another college for a game on Monday Lizbeth gushed "Van, your dad and stepmom are so cool. You're lucky. In fact, I want to be as classy and beautiful as your stepmom when I grow up."

I felt bad when the first thought to enter my mind when she said that was "I wish that you could fuck like her too." I severely chastised myself until I let Van off with a hug goodbye and wished him luck in the next game.

Lizbeth and I talked some more on the way to her dorm, and in the parking lot. I begged off going anywhere else, telling her that I was really tired. She had had a great time at dinner, so she didn't begrudge me taking off. I kissed her goodbye and then instead of driving to my dorm drove to the Four Seasons.

Allegra answered the door of Suite 1501 within a few seconds of my knock. She had a shorty bathrobe on that showed off her long sculptured legs. "Hello Kevin; nice of you to come. I badly need a back massage."

"Uh...what?" I asked, again being a little tongue-tied.

"I twinged something in my back exercising in the hotel fitness center sometime after the game. I gave you the note hoping that you could rub my back a little to make it feel better. You weren't expecting something else, were you?" she said/asked with a wicked grin.

"Uh...no...not really," I whined.

As she discarded her robe, revealing her splendorous naked body, she said "I'll just lie on the bed until you remove your coat and tie and any other items that make you uncomfortable."

With that she lay face down on the king-sized four poster bed in her hotel room suite. I dutifully removed my coat and tie, but also my shirt, pants, shoes, and socks, leaving only my boxers on. She didn't see that since she was facing away from me.

As I lay next to her and massaged her back we engaged in general conversation, mostly carried by her. Some of the topics she wanted to discuss were between bazaar and uncomfortable, including Lizbeth (who she said she liked very much), details of how I scored the winning goal, what I thought about her, and whether I had done any painting using the kit she had given me. After about ten minutes without lifting her head to look at me she asked "Would you be a dear and straddle me while you press hard on my lower back."

"OK," I responded, as I took off my boxers. When I straddled her there is no way that she could not have felt my testicles on her ass cheeks; she didn't feel my cock, however, since it was hard as a rock and sticking straight out. "Oh, yes...right there, Kevin..." she moaned several times. After another few minutes she lifted her head somewhat, said "Wow did you do a good job; do you mind if I turn over so that you can rub my front a little too?"

"No problem," I said as I moved off of her.

When she turned over she couldn't help but see my hard-on. "Kevin, I didn't expect you to remove all of your clothes," she teased. "I guess as a healthy 21 year-old you couldn't help yourself, could you. Just be certain that you properly attend to my pussy before you put that weapon between your legs at my vaginal vestibule," she concluded.

She barely got out the word "vestibule" before my fingers, tongue, and lips were attacking her tiny slit. I juiced her up for three powerful orgasms before I needed to get relief or I'd explode. As she was coming down from her third high I buried my cock in her pussy with one forceful push, eliciting a scream from her. Then as she started choking my cock with her cunt muscles I sawed in and out. She grabbed my neck and moved my face toward her chest. "Start sucking my nipples, you worthless piece of shit," she growled. I did as asked, sucking one nipple while pinching the other, simultaneously with my cock's piston action.

Allegra yelled "Oh my fucking God" as I pulsed jets of seminal fluid into her, and then she came with a vengeance after about the third squirt and clamped down so hard on my dick that I was sure that she strangled every bit of semen out of it.

After two more stupendous fucks, one doggy, the other with me sitting on the edge of the mattress with my feet on the floor and her face-to-face with me, and a very handsy shower, she gave me a little blue pill and a glass of water. "Since you'll be staying here the entire night, you might need one of George's little helpers," she chuckled.

I wasn't sure that I needed it - she turned my on so much I might have been able to go a month straight - but why chance it? So I took it.

As we lay cuddling on a part of the mattress not covered with sweat or bodily fluids I turned her face toward me and seriously said "Allegra..."

She interrupted me and with a smile gently said "'Mrs. Van Rensselaer' if you please, Kevin; it's much naughtier that way."

"OK, Mrs. Van Rensselaer," I smiled, "at the risk of irritating you I really need to ask you two questions. Do you promise not to kick me out if you don't like them?"

Allegra smiled. "If I don't like them I might smack you - but since I badly need to enjoy your sexual services until morning, I won't kick you out."

"Uh...OK then; the first of two questions: do you have any other guys except me that you play with?" I asked, wincing in anticipation of her slapping my face. Instead she answered quickly and decisively without rancor.

"No, I don't. Since I started dating George the only two people I've had sex with are you and him."

I sighed, relieved in many ways. "My second and last question; as beautiful, sultry, intelligent, and classy as you are why did you seek me out to have an affair with?"

Allegra bit her lip and a few tears actually formed in one eye. After a long pause I said "Look, it for some reason it's hard for you to answer that, don't; I withdraw the question."

"No," she responded, "I think for both your edification and my emotional well-being I need to answer that."

She then got out of bed and walked over to her suitcase. Seeing her entire naked body got the expected result at my crotch, but she didn't pay any attention to it as she handed me a 5 x 7 inch photo in a light frame. It was a photo of me leaning on a large tree, wearing a T-shirt and in shorts, and smiling. However, there were several problems with it.

The first problem with the photo was that the only time that I remembered having a photo taken with a backdrop like that I was seventeen, and the way I looked in the photo was what I looked like now at 21. Second, I don't remember ever having my hair that long, and certainly not recently. Third, I was wearing a Princeton T-shirt, and I never owned one and don't remember ever wearing one.

"Did you Photoshop this picture of me?" I asked after viewing the photo carefully for a full minute. "I don't remember ever wearing a Princeton T-shirt and I've never had my hair that long."

A few more tears formed in Allegra's eyes before she responded. "That's not a photo of you; that's a photo of my dead first husband, Brandon, the love of my life, on his 22nd birthday when he was going to graduate school at Princeton."

I gulped hard - in fact I think that my brain started swimming a little and if I had been standing up I might have fallen and hit my head. Suddenly the look on Allegra's face and her temporary loss for words when we met at her wedding to George came storming back into my brain. "Is that why she gulped so hard, her eyes bulged out, and she lost her composure for a few seconds when she met 17 year-old me?" I asked myself.

I looked at the photo again; damned if I could tell it wasn't me without the discrepancies earlier alluded to; he definitely was my doppelganger. I didn't know what to say or do. After another delay Allegra wiped the tears from her eyes, took the photo from me and carefully placed it on the nightstand next to the bed. Then without further ado she shinned down to my cock, sucked it from ¾ hard to fully hard, and then mounted me cowgirl. I mauled her tits while she seemingly tried to rip my dick off, before we had completely debilitating mutual orgasms.

After we separated, before we fell asleep, I mumbled into her ear "I love you."

Her eyes quickly darted to mine, she got a crooked grin, and replied "I know." Then she started quietly sobbing (something I had never seen her do) and buried her face in my shoulder while I held her tightly. My brain seemed to be fried from everything that had happened that day (or was it already the next day by now), but I was so physically and emotionally drained that I soon was in dreamland.

I woke up with a kiss from Allegra; when I looked at the bedside alarm clock it read 7:22. "I have a 9:30 flight, Kevin. Do you think that you could give me a ride to the airport so we could have more time together? After a fun shower, of course," she said with a big grin, and then another kiss.

We did have a fun shower, in the large ornate shower stall in her Four Seasons' suite bathroom. In addition to much body contact and nipple and testicle massaging, I entered her from behind as the water splashed over both of us from six different nozzles, resulting in a truly spectacular set of mutual orgasms. Before we got dressed I snapped a photo of her on my iPhone as she was slightly bent and reaching for her bra.

When I dropped off Allegra at the airport she held my face in her hands. "Two things, Kevin; first, I apologize for laying the information about my deceased first husband on you, but it was the legitimate answer to your question." She kissed me, gulped, and then continued. "Second, I would really like it if you would do an oil-on-canvas portrait of me. Maybe you can do one this summer."

I smiled: "No problem with the first, and I'm way ahead of you on the second."

She planted a passionate toe-curling kiss on me and then grabbed her suitcase and entered the airport without a backward glance.

As usual whenever I dealt with Allegra - especially after our unmatchable sexual bonding - my mind was fucked up for days. How could it not be after she dropped the bomb of her doppelganger first husband on me, me telling her that I loved her, her response of "I know," and then sobbing herself to sleep in on my chest? However, I was highly motivated and despite the demands of classes, lacrosse, and a social life, I was able to get my mind straight and do a portrait of Allegra from the photo that I had taken, using the materials from the expensive art kit that Allegra had given me. So that it could be viewed by others without exposing our sexual relationship I gave her face and some naked body parts an ethereal quality so that it would be impossible to recognize her. When I was done with the portrait - on an 18 x 27 inch canvas (a golden rectangle) - I boxed it securely and expressed it to Allegra.

Allegra called me after receipt of the portrait and seemed to be very emotional when she thanked me for it. "I'm going to get a gallery to display it," she told me, but I didn't put much stock in that.

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When I returned home in the summer between my junior and senior years of college I got the news that by the time that the school year started again my parents would be moving to Florida. That was not even close to the weirdest thing that came about that summer, however.

After I had been home only a week, and had yet to see Allegra, George called me. After an exchange of pleasantries, including how much he had enjoyed his trip to watch Van and I play lacrosse (he didn't enjoy the trip nearly as much as I did - although his mind probably didn't get fucked up like mine did either), he got to the point. "Kevin, I need a favor. As you may or may not know Allegra has organized a charity ball for leukemia research for two weeks from this Saturday at the Grand Hotel, and I'm going to be out of town on business that weekend. Could I impose upon you to escort her to the ball?"

I was flabbergasted; of course I would agree - but apparently I had paused while things were playing out in my mind. That apparently gave George the impression that he needed to sell it to me. He promised to pay for my tux rental and the limo, and a new pair of shoes if I needed them, and apparently was willing to go further when I stopped him. "Sure Mr. Van Rensselaer, I'd be happy to take Mrs. Van Rensselaer."

"Great; I'll have her call you about details," he replied, and then after some more small talk terminated the call.