Mom takes son to fancy whorehouse for his first time

As I was driving my son and myself across the Brooklyn Bridge into New York City, I couldn’t help recalling the saddest time in my life. Almost two years ago, I stood vigil with my husband as the cancer he’d battled for several years took him from us. We spent the last few days discussing his triumphs and the things he’d failed to do in his lifetime.

Charles was a good man. We’d met in college and married my senior year, me already six months pregnant with our son, Chad. I had a difficult delivery and we wound up having only the one son, although we tried for more children over the years. Charles was a good looking man, light brown hair and brown eyes, a stocky wrestler’s build (he went to college on a wrestling scholarship), a winning smile and the confidence of a man who knew what he wanted and was able to get it. Mostly, it turned out, he wanted me. I fell in love with him the first time I saw him. We quickly became passionate lovers and then married with Chad on the way.

We had several wonderful years together. Chad was twelve when the cancer first appeared. Over the next four years, my Charles fought it valiantly before finally succumbing to the disease. Chad, now sixteen, stood by my side at the funeral, the spitting image of his father who would have been proud of the man his son had been forced to suddenly become. Over the two years since we buried Charles, my son and I have become very close. I doubt I could have gotten through my mourning period without my son to lean on.

I’ve become very attached to my son. One could almost call me a jealous woman. I haven’t liked any of his girl friends and am almost ashamed to admit I am happy he is currently unattached and even more pleased that he has kept a promise to his father to remain chaste until he turned eighteen.. For his part, he’s been urging me to return to the dating scene…to find a friend and possibly a husband. When I’ve scolded him about it, telling him I’m too old for such nonsense, he just laughs and tells me what a beautiful woman I am.

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“Christ, Mom, you’re only forty years old. And you’re a great looking woman. I bet there are lots of guys who would give an arm and a leg to marry you!” he would tell me. I don’t know, maybe he’s right. I’d like to think I’m still kind of pretty. I’ve always been blessed with good skin and I’ve kept my figure. My boobs aren’t sagging much, despite the weight of having 36 DD breasts. At one hundred-eighteen pounds and five foot-two inches, I’ve kept my 36-24-34 figure. My legs still draw a whistle when I get brave enough to wear a short skirt or go to town in my jean shorts. And I am very vain and proud of my hair, long black tresses that fall to the middle of my back.

I love it when Chad tells me how pretty I am, even though it makes me feel kind of naughty to hear my own son talk that way. My friends have teased me about how I need to cut the apron strings and quit being possessive and jealous over Chad.

Which make today’s visit to the city even more difficult. Today, I am fulfilling one of my husband’s last wishes. Today, I’m taking my son to visit the city’s most luxurious bordello. My heart fluttered as I thought of the ornate business card in my purse that carried the words, “Fulfillment, a Tradition Since 1850,” followed by a phone number.

I had long known about the tradition in Charles’s family about the father taking his son to Fulfillment, New York City’s oldest and finest whorehouse, for his first sexual adventure. Charles had been taken there by his father who had been taken there by his father and so on. Charles said the legend was that his father’s male ancestors had been among the first patrons of Fulfillment way back before the Civil War.

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I was also aware that occasionally Charles visited Fulfillment during our marriage. We both had grown up in promiscuous times and in our younger days had done some swinging with friends in the neighborhood, trading partners for an evening or even a weekend. Otherwise, I had never had an affair or even a one night stand, I knew Charles wouldn’t have minded but I was never really tempted. It never bothered me that Charles went to Fulfillment on occasion, it even excited me when he’d describe some exotic beauty he had fucked and we always had great sex afterwards.

As Charles lay dying, he asked me to follow through on the tradition with Chad when he turned eighteen. I was both horrified and amused, a mother taking her son to a brothel for his first fuck? Charles pressed me on it though, making me promise that the tradition would continue. I couldn’t refuse my husband and I finally agreed. Charles explained how things worked at this exclusive whorehouse. For a specific fee, one had lifetime privileges at Fulfillment. When my husband told me the fee, I had gasped, but Charles just laughed and said his own father had set aside money just so Chad could continue the family tradition. He gave me their business card and I tucked it away until a few days before Chad turned eighteen. I thought about it often, struggling with my own jealousy and the sheer weirdness of it. I was sure that Charles would have found my thoughts amusing.

I took the card from my jewelry box and while Chad was out with friends, called the number. A young sounding, very feminine voice answered. “Fulfillment, this is Alexis. How may we please you?”

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“Um, my name is Diana, Diana Martin. Charles Martin was my husband.”

“Oh yes, Mrs. Martin. Please accept our condolences on the loss of your Charles. He was a good man.”

“Thank you,” I almost whispered.

“I guess you are calling to make an appointment for Chad, yes, Mrs. Martin or might I call you Diana?”

“Please. Um, yes, my son turns eighteen next week.” I was astonished that without a pause, this woman was talking as if she’d known us all our lives.

“Wonderful,” the sexy voice chuckled. “Have you asked Chad for his preferences?”

“Uh…preferences, Alexis?”

“Oh yes, Diana. Fulfillment will grant his wish as to the type of women Chad prefers. His family legacy is to be with one of our finest ladies on his eighteenth birthday. We will provide the lady of his dreams, be she an eighteen year old cheerleader or the sexiest grandmother in New York City, Caucasian, African American, Hispanic or Asian.”

I was almost speechless. Charles hadn’t informed me of this. “I…um, I honestly don’t know, Alexis. This is all so new to me.”

Alexis giggled over the phone. “I understand, dear. You should talk to Chad. Get him to tell you what his fantasy woman is like. Just make sure you call us back over a day or two before his visit so we can make the appropriate plans.”

We ended the call and I spent the next three days trying how to get the necessary information out of Chad. I mean, how do you ask your own son, “Honey, describe your dream fuck!” I wanted this to be the wonderful night that Charles would have provided his son, but it was going to be difficult. Chad had dated some in high school, but hadn’t gravitated to any particular type of girl as far as I could tell.

I finally broached the subject while Chad and I were out to dinner at our favorite Italian restaurant. As we ate, I kept prodding Chad about various young ladies in the restaurant. His responses were of the usual, “I dunno…I guess,” variety when I’d ask if this young lady or that young lady was pretty.

Chad finally put down his fork and looked at me quizzically. “What’s up, Mom? Why do you keep asking me about girls?” This after I’d asked him if he thought our waitress, a pretty, buxom blonde, was pretty.

I could feel my face redden as I stammered, “Well…uh, I was curious. I wondered if there was a particular type of girl you found attractive. Maybe your old Mom is trying to fix you up!”

Chad looked at me with a surprised expression. “Are you serious, Mom? You really want to know the kind of woman I think is hot?”

“Well, yes. I am curious.”

Chad nodded, a little amused. “Okay, Mom. Let’s see…” He turned and looked about the room. Finally, he gestured a particular direction. I looked over to see a family of four sitting in a booth. Next to a woman about my age, was a teenaged girl maybe sixteen years of age with long red hair and a pretty, innocent face.

“Oh Chad, she’s lovely. I bet she’s about your age, too.”

Chad snorted and said, “Not her, Mom! The woman next to her…her mother.”

I almost gasped. “Her mother!” I studied the woman. She was my age or maybe a little older. Taller than me, but heavy breasted with dark, red hair. I turned and looked at my son. “You’re telling me you prefer older women?”

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It was my son’s turn to blush. He shrugged his shoulders and replied, “You asked me, Mom. Yes, older women turn me on!” For some reason, his words sent a thrill through me.

“Look around some more, honey. See anyone else that uh, turns you on?”

Chad stared around the room some more, finally settling his gaze on a couple dining at an open table; a husband and wife, both in their mid forties. The woman was very lovely. A blonde with large breasts, her dress revealing a serious amount of cleavage and most of a shapely leg peeked through a long slit in her dress. “She’s pretty sexy, Mom,” Chad stated seriously.

“Anyone else?” I asked. A shiver traveled through my body, ending up between my thighs. I realized with a bit of surprise that my pussy was wet. I shivered again as I relished that sweet sensation of my labia lips rubbing together, becoming slick with my own juices.

Chad studied the crowded restaurant. He grinned and waved. “Look, there’s your friend, Mrs. Brown. I think she’s really hot!” I looked around and gasped. Just being seated across the room was my best friend, Jill Brown and her husband, Tom. A lovely woman, about my height and weight…her hair almost the same color as mine and our figures were so close, we could and have, borrowed each other’s clothes. I managed a feeble wave and smile at the woman many people say resembles me so much that we could pass for sisters! Jill was wearing a off the shoulders summer dress.

I turned, barely able to look my son in the eye, feeling my face flushing…my skin like it was on fire. “You really think Jill is sexy, huh?”

Chad waggled his eyebrows in a lewd expression and replied, “Oh yeah! A woman that looks like Jill is about the sexiest thing alive, especially wearing that outfit! I think bare shoulders are sexy!” I stifled a groan as I felt my juices almost shoot out from my pussy. I was sure my panties were becoming soaked and wouldn’t be surprised if I left a puddle on the leather covered bench in our booth. I realized that I was wearing a shell blouse myself that left my shoulder’s bare and bared the upper portion of my breasts.

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“I can’t believe what you’re saying, Chad. Good grief, all these women are my age.” I tried to hide the sudden nervousness in my voice.

Chad grinned and said, “What can I say? I reckon I just want to find a girl like the girl dear ol’ Dad found!” His eyes seemed to crawl over me and then he blushed and suddenly found his linguini very interesting.

When our conversation resumed, we drifted on to safer topics. Our dinner passed pleasantly, but we were both aware that we were giving each other funny looks now and again.

The next day, I again called Fulfillment and spoke with Alexis. I described what I hoped was Chad’s preference, embarrassed as I described essentially myself to the woman, adding his likes in clothing. “Mmmm…very interesting, Diana,” purred Alexis. “I know who would be perfect for Chad. We’ll see you Friday evening at eight!”

The next few days, I was filled with all sorts of mixed emotions. I constantly argued with myself that Chad had meant nothing when he had been commenting on his tastes in women. Another part of me, the part that was responsible for my constantly wet pussy, argued that Chad had been flirting with me…his own mother! That he was sending me a message. Another part of me was filled with jealousy at the thought of another woman…any woman introducing my son to the world of sex. Through it all, only one thing kept me on course and that was my solemn pledge to my late husband to see this through to the end…to keep up the Martin Family tradition!

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Friday, Chad’s birthday, he and I drove up to New York City. It was a two hour trip and I finally broke the news to Chad of what his father’s great gift was and of the long established family tradition. My son was dumbfounded…totally speechless for the longest time. Finally reality set in and a big grin broke out on my son’s face. “Wow!” he kept saying over and over.

Chad suddenly sobered up and said, “Are you okay with this, Mom? You don’t mind?”

I wanted to scream at the top of my lungs that of course I minded, that my son’s heart and body should belong to no one but me, but I smiled and replied, “Of course not, Chad. This was your father’s last wish for you, son.”

He seemed satisfied with that and we lapsed into silence for most of the ride. I know he was thinking about his impending evening though. A bulge began to grow in Chad’s pants…a sizable bulge and I had a hard time concentrating on traffic.

Finally we reached New York City and drove to the address Alexis had given me. It was a posh, old mansion. An attendant took our car while an elegantly dressed butler walked us past Grecian statues of Gods and Goddesses and inside to a sitting room. The place reeked of money and power and taste. Erotic paintings hung on the wall and here and there were placed art objects, intensely sexual in nature. We waited just a few minutes, both of us trying not to giggle from nervousness, when in walked two lovely women.

“Good evening, Diana. Good evening, Chad. We’re so thrilled to finally meet you. I am Alexis.” Alexis was a beautiful Eurasian woman. She was wearing a Christian Dior suit that hung perfectly on her lovely form. Her short, black hair was perfectly in place, except for a thick strand that hung attractively over her right eye. She approached us and kissed me on the cheek and then shook Chad’s hand. “We’re thrilled to finally meet you. I know Charles would be thrilled to see your family tradition continue!”

Chad was almost speechless and I managed a quiet thank you. There was a moment of awkward silence and then Alexis continued. “So, Chad I know you’re anxious to get started. There are some formalities we need to take care of.” She turned and gestured to the other woman, a short, gorgeous redhead, with an attractive zaftig figure wearing a white medical coat. “This is Doctor Claire. Chad, you’ll need to step out with her. She’s going to take a little blood test and check you out a little while your mother and I have a little chat, okay?”

Claire stepped up and took Chad by the hand. “I’m so pleased to meet you, Chad…Diana. Shall we, Chad?” She led my son away while Alexis gestured for us to sit.

She reached out and took my hand. “So, how is Mom doing? Are you okay, Diana?”

I let out a nervous laugh. “I guess so. I can barely believe I’m here, bringing my son here for his first…um…”

“Experience?” suggested Alexis. “I understand. I know it’s difficult, filling in for your husband, but I’m sure he’d be so proud of you. It’s not every woman or every mother who could be so open-minded.” She squeezed my hand and her touch seemed strangely reassuring and a little more. Her dark eyes seemed to draw me in. I’ve rarely felt attracted to a woman, but I felt more than a little tingle from her touch and from her gaze. I felt my nipples begin to harden against my bra.

“Well, lets get the formalities over with. You have the fee?”

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I reached into my purse and took out a thick envelope. This night would be expensive, but Charles and his father had planned this well. If this place was everything Charles had said it would be, the money would be well spent. Alexis took the envelope and slipped it into her jacket pocket.

She picked up a file folder and handed it to me. Here is Doctor Claire’s medical report on the lucky lady that will be with Chad tonight. She passed her medical checkup as well as tests for STD’s earlier today. Here at Fulfillment, we check each of our ladies every day that they are working.”

“Wonderful,” I replied, amazed at the clarity of the report.

Alexis leaned in again and squeezed my hand. “We find most of our clients prefer not to have to deal with condoms…you know how men are.” She grinned and continued, “And I’ll confess, many of our ladies also prefer it, sans condoms…it raises the level of intimacy. Of course, Chad can opt to wear protection.”

I felt my skin heat up. “Um…it’s his choice, but he’s in such a state, I expect he won’t even think about it.”

Alexis laughed and then continued to fill me in. Chad and his future lover would have the next twelve hours to do…well, whatever Chad wanted as long as it didn’t involve violence. We took a tour of the mansion. Alexis showed me the kitchen and introduced me to their cooking staff. “If your young man requires nourishment to keep himself going, he or his lady can simply call down to the kitchen. My lovely guide held hands with me as she led me up the winding staircase and showed me Chad’s bedroom, a lavishly furnished suite with the biggest bed I have ever seen. Large mirrors decorated each wall.

“Most of our clients like a lot of playroom,” Alexis chuckled, winking at me. She showed me the closets, full of fantasy clothes, various leather, vinyl and plastic instruments and toys. “Just in case any little fantasy needs to be carried out,” said my guide. Alexis picked a long two headed, rubber dildo up off a shelf. “This is one of my favorites,” she whispered coyly, winking at me again.

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“Oh! So you also do…uh,” I trailed off…my naïve upbringing showing up.

Alexis laughed and said, “Well, these days, I’m primarily management. But now and again, I like to spend time with special clients.” I felt a spurt of my juices, soaking my already moist panties. I was amazed at how my body was reacting to this lovely woman.

We returned to the sitting room to await Chad’s return. We drank coffee and idly chatted, mostly about Charles. “Of course, we didn’t see much of him after he married you, but when he did visit, he talked about you constantly. I’ve wanted to meet you for a long time,” Alexis said.

“Well,” I stammered in reply. “He didn’t mention any of you by name, but he told me about your…his adventures, and well, we always had great sex afterwards!” That seemed to please her.

She seemed about to say more, but a chime rang and Doctor Claire walked in with my son. He was flushed, obviously aroused judging by the large bulge in his slacks. Again, I felt a shivering delight spreading wetly between my legs. “Well, this young man is as clean as whistle and ready for love!” announced the doctor.

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