After getting divorced in my mid-40s, I did not really see much excitement in store for me. The split had been fairly amicable, and my ex, Lynn, both came from an affluent background and earned more than me. We had no children, so there were no issues on that front. I figured that, after a few more years at my public sector job, I would take early retirement, maybe travel a little. I had no idea that the most thrilling chapters of my life had yet to begin.
They started innocently enough. The first Thanksgiving after my divorce, my friends Jim and Jen invited me to spend a few days with them in the suburbs north of the city where we had all met and where I still lived. Jim and Jen were a few years older than me with grown children. Their older boy lived out of state and did not join us, but their daughter Danielle also came to Thanksgiving dinner. She was attending college in the city. When Danielle first moved there, her parents had passed along our contact information, in case she ever needed anything. But, Lynn and I had never heard from Danielle during her freshman year. I was slightly disappointed, because I had always felt something of a connection with Danielle. Growing up, she had been extremely shy and bookish, reminding me of myself as a teenager. In high school, she had adopted a gothic look: a nearly all black wardrobe, heavy on the makeup and jewelry, with her hair often obscuring her face. She held onto the style into college, but her easy laughter and friendly manner at dinner spoke of a newfound confidence.
In fact, Danielle was independent enough that she insisted on returning to the city after dinner. Rather than spend the weekend at her parents’ well-appointed home, she was adamant that she needed to get back to work on a project for one of her classes. By that point in the evening, Jim had had quite a bit to drink. In contrast, I had been careful to limit my alcohol since the divorce. Thus, I did not hesitate to drive Danielle to the commuter rail station.
Their town was at the end of the line, as much rural as suburban, so it was a good 20-minute drive to the station. Although I thought the area was beautiful and had considered relocating out of the city many times over the years, I could see where the region would not hold a lot of interest for a 19-year-old like Danielle and why she might be anxious to return to her friends in the city.
With what little traffic there was in the area all but gone due to the holiday, we were early for the train. The weather had taken a wintry turn, so I parked and kept the car idling so that Danielle did not have to wait on the exposed platform of the station.
Knowing how tight money was when I was in college, I dug out my wallet, took out a pair of $100 bills, and offered them to Danielle, “Here, get yourself dinner or something.” Danielle protested, but I insisted that it was the least I could d0. At length, she said thank you and stuffed the bills into her coat.
Then, her lip curled into a sly smile. “You know, Uncle B–,” she said. “I really appreciate the gesture. But, the truth is I’m not hard up for cash. My parents are paying my tuition, and I found a very lucrative job for spending money. In fact, I really don’t need to get back to school, but because I expect that this could be a very profitable weekend.
“See, I’ve been working as a masseuse the last couple of semesters. Holiday weekends tend to bring in a lot of business. Either loners who stay in town, or family men trying to get away for a little bit. And, I have to tell you, for what you just gave me, you wouldn’t be entitled to a very relaxing session.”
As she spoke, Danielle edged closer and leaned in toward me. First, she put her hand on my thigh. Then, she slid her long fingers between my legs. She concluded by giving my balls a firm squeeze. I could not help but gasp, prompting a playful laugh from Danielle.
“Really, Danielle-,” but she silenced me by placing the index finger of her free hand gently to my lips.
I knew it was wrong. But, I had had precious little experience when Lynn and I began dating, and I had remained faithful to her for almost 20 years. As you might imagine, we had not exactly been setting the sheets on fire in the lead up to our divorce. And I had been with no one since. All told, it had been well over a year since I had known the touch of another, except for the occasional platonic hug. And even those from some of my women friends had begun to give me a jolt of excitement. Danielle’s probing young fingers caused me to respond instantly.
Wordlessly, Danielle undid my belt and pants. She reached into my shorts and pulled free my swollen cock, which immediately became rock hard in her hand. Slowly, she started to pump my shaft. I looked down at her slender fingers, wrapped in rings, rising and falling along my member. Then I looked up nervously to see if anyone was watching, but the windows were fogged by our breath.
I closed my eyes and exhaled in surrender and disgust at myself, but my hips began to gyrate under Danielle’s ministrations.
“It’s okay,” she said. “It’s all right.”
I opened my eyes and could sense her staring at the side of my face. I turned and looked at her. Danielle had matured into a beautiful young woman. About 5′ 10″ and rail thin, she had a gamine-like quality about her. Her mother, Jen, was of Japanese descent, and from her, Danielle had inherited silken black hair, clear, olive skin, and slightly oval eyes. From her Irish-American father, she had taken a lightness to her eyes. When I looked into Danielle’s gray-green eyes, I exploded like a teenager, shooting a geyser of cum up nearly to my face. At first, Danielle seized the base of my cock in a vain effort to control my orgasm. But, as at least a month’s worth of cum poured forth from my balls, Danielle pumped my shaft to drain every last drop.
“Wow,” she laughed, looking for something to wipe off her hand. I found a towel in the backseat and offered her some hand sanitizer.
“I’m sorry,” I said, as I struggled to stuff my still-stiff cock back into my shorts and fasten my soaked pants. “I guess it’s been a while.”
“That’s okay. It’s a turn on to see someone so turned on.”
I was both grateful and resentful to hear the horn of the approaching train.
“I guess I should go,” said Danielle. She grabbed her bag from between her feet on the floor and opened the door. Then she leaned in and kissed me quickly on the lips. “Why don’t you look me up when you get back to the city?”
***
Fortunately, Jen was asleep and Jim drowsing by the time I made it back to their home, so I didn’t have to explain the stains all over the front of my pants. I cleaned up in the bath off their guest room. As I climbed into bed, I was, despite pangs of guilt, already aroused again by the evening’s events. Although it might have been the prudent course, I did not want to masturbate into just a wad of toilet paper. I looked through my bag for a spare garment and thought of using a sock like I was still in high school.
Then something popped up from my subconscious. Earlier in the day, Jen had mentioned throwing some of Danielle’s things in the laundry. On the way to the guest room, I had nearly tripped over a laundry basket of neatly-folded clothes outside Jim and Jen’s bedroom. Putting on my soiled pants, I crept out into the hall and down to the laundry basket, dimly illuminated by a night light. I could hear the TV downstairs and Jim lightly snoring.
Sure enough, on top of the laundry were several pairs of tiny panties that had to have belonged to Danielle. Although there was a red pair and a green one, I selected one of several white pairs with which I slunk back to the guest room. I barely had the door closed before I had my cock out and vigorously jerked off thinking about Danielle’s graceful fingers teasing my shaft barely an hour before. I shot another giant load into her panties, which were not nearly large enough to absorb all of my cum. I had to run to the bathroom to keep from dripping on the carpet. I cleaned up, hid the panties in my bag, and fell into a deep sleep.
***
I did not see Danielle, at least not in person, for another year. I returned to the city with thoughts full of her. At first, I thought that I did not have Danielle’s cellphone number and spent several days trying to think if there was a tactful way to ask her parents for her number without raising suspicion. But one day unpacking one of the boxes stacked in the corner of my apartment since I moved in, I found an old address book my ex-wife had maintained. My chest filled with hope, then joy, when I found a number for Danielle. I quickly programmed the number into my phone. For the next several weeks, I periodically found myself with my thumb poised over the number. But, guilt and cowardice kept me from ever placing the call.
Instead, I began trawling the escort sites. Even before my encounter with Danielle, I had contemplated seeking professional companionship and had begun looking online every once and awhile. But, now I began researching the best sites and searching them diligently. Soon enough I found her posts. She advertised as Isis, promising fully relaxing bodyrubs with the possibility of other kinds of sessions, but no full service.
The first post I saw had an enticing picture of Danielle in stockings, garters, and lingerie, her face obscured by her dark hair and the low light. But Danielle’s willowy body and long, delicate hands left no doubt that it was her. I knew Danielle had an interest in photography, and sure enough, she frequently changed the photographs that accompanied her ads, along with the text of the posts themselves. I looked forward to every new post, new outfit, new pose, and a playful come on that promised the bliss that I knew she could deliver. Many nights I pleasured myself to Danielle’s pictures and words and fantasies of what it would be like to be lying naked under her hands.
Over time, I saw posts from other providers using the same number and worked out that Danielle and some other girls worked out of an apartment not far from my own. Danielle seemed to work two or three days a week. Her proximity only made me fantasize more ardently about her.
Nonetheless, month after month, I could not bring myself to call her. I told myself that it was a betrayal of my friends’ trust, which it was. I told myself it was an unseemly cliche for a man my age to chase a much younger woman, which it was. But, it was more than that.
For Danielle was not exactly my friends’ daughter. She had been born Daniel, my friends’ son. The shy, artistic boy he had been was the teen who reminded me so much of myself growing up. When he was 16, he began dressing in women’s clothes and asked to be addressed as Danielle. Although her parents were always supportive, I cannot begin to imagine what she faced in her small town. And given our similarities, I could not help but wonder if I might have chosen a different path if I had come of age in a different time. These realities only deepened my confusion and hesitation.
***
Jim and Jen had had to coax me to join them for Thanksgiving that first year after my divorce. The following year, I readily and gratefully accepted their invitation. It was all I could do not to ask point blank if Danielle would be there. I settled for asking if she needed a ride up from the city. When Jen said that she would pass along the offer, my chest filled with anticipation just knowing that Danielle would be there.
My spirits fell when Danielle did not reach out to me, rose again seeing her at dinner looking even more stunning than she had a year earlier, and fell as she all but ignored me throughout the day. I did myself no favors with my awkward efforts to initiate conversation with her. Eventually, I fell largely silent, lest my infatuation become too obvious.
After dinner, Danielle announced that she was going to meet some friends. When Jim told her to be careful on the roads, she said that she was going to take a car service. I took the chance to offer to drive her. She casually turned me down, until she realized that it would take close t0 30 minutes for a car to arrive on the holiday. I fairly leapt from the couch when Danielle begrudgingly said, “Oh, all right,” and gestured for me to follow her to the driveway.
It was another cold night outside and even icier in the car. Danielle stayed focused on her phone and rebuffed my efforts at conversation with monosyllabic responses. Finally, when we were well away from her parents house, Danielle told me, “Pull over.”
We were on a dark stretch of rural road. As soon as I stopped the car, she said accusingly, “You never called me.”
“Danielle,” I began. “I didn’t know what to say. Your parents.”
“And now look at you, acting like some simp in front of them. Do you think I want them to know what I do or what we did?”
I was too ashamed to answer. But, Danielle continued, “Is this what you were hoping for? To get me out by the side of the road again?” I tried to protest, but her fingernails dug into my balls through my pants, and I leaned my head back in pain and ecstasy.
“You sick old pervert,” she scolded. But, she also got up on her knees in the passenger’s seat. She savagely opened my pants and pulled out my cock, which immediately became fully engorged for her. Her right hand took firm hold of my balls and the base of my cock. She shook her head in seeming disgust then she began running her tongue up and down my shaft.
She stopped momentarily to ask, “You like that?” As if my moans, gyrating hips, and already dripping cock did not provide the answer, I reached over and grabbed her firm young ass. As she began sucking on the tip of my cock, swirling her tongue around the head, I reached up under her leather skirt and began kneading her firm, athletic ass. Now Danielle took all of my cock in her mouth and throat. My hands began to tease her asshole through her panties. My fingertips occasionally grazing her balls straining beneath the fabric of her undergarments.
Suddenly, I could control myself no longer. I warned Danielle that I was about to come and grabbed her shoulders to push her away. But, she swatted my hands aside. And, as I erupted with one of the most thunderous orgasms I had ever experienced, Danielle sucked hard on my cock, continuing to bob on it, slowing only as did my own spasms.
When I was through, Danielle delicately withdrew from my shriveling cock, careful to keep her lips tightly shut. She primly resumed her seat, rolled down the window, and then spat my seed on the ground. She brought out a water bottle from her bag, rinsed and gargled several times, spitting out the window. She put away the water, took out a tin of breath mints, and popped two in her mouth.
She turned to me and shrugged in irritation. I had simply been staring at her the whole time. I quickly zipped up my pants, did my belt, and started the car.
“Wait,” she said, holding out her hand. It took me a moment to understand what she was asking for. I handed her my wallet, and she took out the several hundred dollars inside. She tossed the wallet into my lap.
“This is the last time like this,” she warned. “If you want to see me again, you call me at home, you call me at work, but you call me like a gentleman.”
“Yes, Danielle.”
***
A little more than two months later, I found myself standing outside the door to Danielle’s apartment, my throat dry with nerves. I had first called her at work. For some reason, seeing her professionally seemed less of a transgression. I tried giving a fake name, perhaps to further distance myself from my actions. But, she saw right through that. Still, to my great relief, she agreed to see me and seemed genuinely pleased when I arrived.
I had never experienced anything quite like it. When I reached her work apartment, Danielle had me strip and lay on a professional massage table wrapped in clean linens. She then proceeded to give me a very thorough and relaxing massage. I did not realize how knotted my shoulders and back had become hunched over a computer for years.
More than that, by that time, except for my brief encounters with Danielle, it had been at least a couple of years since I had known intimate, physical contact. Even before she began to exert any real force on my muscles, I found myself jumping under even the lightest of touches from her. By the time she took a warm towel to wipe the oil off my back, it felt as if my every cell was both relaxed and shot through with electricity.
My excitement only increased as Danielle began to run her nails lightly up my back and thighs. Working up the inside of my thighs, she began brushing my swollen balls. I began easing my legs apart to give her readier access. Then she began sliding a finger on either side of my scrotum. I reflexively lifted my bottom, and Danielle seized my testicles in her hand.
“That’s right, daddy,” she said, using her free hand to give me a light rap on each cheek. She began fondling my balls while reaching up to stroke my hair. With Danielle gently guiding me by the testicles, I lifted my bottom higher and higher. Eventually, I lifted myself up on my elbows, and Danielle reached underneath me to swirl her hand up and down my shaft. I involuntarily moaned, and she gave a satisfied sigh.
“Would you like to turn over?” she asked.
I slowly worked onto my back, as Danielle stepped away from the table. I could not believe how aroused she had gotten me with just her hands. Now, she stepped up to the table with her hands cupped together. I noticed the rings on most of her fingers and arrays of bracelets running up her forearms. The long earrings against her graceful neck. In her hands was warm oil that she slowly let seep out over my cock. She slicked the oil all over my shaft and balls. She resumed fondling my balls and running a finger of her free hand along my cock. I instinctively reached for her, but hesitated.
“It’s all right, you can touch me,” she said.
I ran my hand from the small of her back to the nape of her neck, which I began massaging.
“Mm. That feels nice,” she said, turning her bottom slightly toward me. After a few more moments of teasing my shaft, she began to stroke it gently. I could not resist letting my hand drift down to caress her long, toned thighs. As Danielle began to pump a little faster, I dared to reach under her denim skirt and to feel her steely buttocks. Danielle began working my rod quickly now, and my hand ventured between her legs to fondle her balls as she had mine.
“Easy,” she said, momentarily taking my wrist to guide my hand back to her buttocks. “Not here.”
I had only a moment to fear that I had offended her, before her expert hands had me gripping the massage table as I lifted my pelvis in the air. “Yes, yes,” I gasped before coming as hard as I had in years.
When I was through, Danielle kissed me on the cheek. She helped me clean up, and I tipped her generously, still unable to believe she had provided such pleasure almost exclusively with her hands. When she saw me to the door, she handed me a card with her personal number on it.
“You can give me a call any time and come to my place,” she said. “We can do what we want there.”
Two weeks later, I was outside her door, not far from her workplace. I was not sure if it was a date or an appointment and had been too nervous to ask when I called her. So I made sure to dress nice and pick up a bottle of good wine. Maybe she had had the same conundrum, because she was absolutely stunning when she opened the door.
Putting aside her goth air, she had her dark hair swept up off her long neck. Unobtrusive make-up highlighted her cheekbones and eyes, but mostly her olive skin shone through. She had on discreet stud earrings and another tiny stud in her nose. She had a lacy choker around her neck, exquisite bare shoulders, and was otherwise wrapped in an elegant, but form-fitting, gown. The gown was slit high up her left thigh, and with her leg slightly forward, I could see the top of her thigh-high stockings. In her heels, she was nearly six feet tall.
“Oh, my God, you look incredible,” I gushed.
“Thanks,” she said with a smile. “Come in.”
“And thank you for this,” she added, taking the wine. “Why don’t I pour us a glass?”
Danielle led me by the hand to the living room, where I was both relieved and disappointed to see a massage table set up. Still, we had a pleasant chat over our wine about how Danielle liked living in the city and her classes. As we neared the bottom of our glasses, she gestured toward the table and asked, “Would you like to get comfortable?”
I undressed as she took our glasses to the kitchen and then went into what I assumed was the bedroom. When she came out I was lying naked on the table. Danielle was in heels, stockings, panties, and a bustier, all black. I was aroused at the mere sight of her.
“I’ll say it again, you look incredible,” I said.
“Thank you. You’re sweet.”
As I put down my head, Danielle hoisted herself on the table and straddled my legs. Using lotion, she massaged my aching neck and back, putting me entirely at ease. Nearly entirely, anyway. There was something thrilling about having my legs pinned between hers. Eventually, she spun around, straddling my lower back to begin massaging my legs. After working the back of my thighs and my calves, she began working the inside of my thighs, parting them slightly. I am sure my excitement was obvious at that point. She spun around again, this time nestling her slender legs between my thighs and began rubbing my buttocks.
“You have a very nice bottom, you know,” she commented.
“Thank you,” I murmured. “I run to try and stay in shape.”
“Mm, it shows.”
She began alternating kneading my buttocks with scratching them with her nails. Then I felt her thumb push between my cheeks and caress my asshole. I gasped slightly and my breathing shallowed as she toyed with my ass. I began to raise my ass in the air toward her. And Danielle inched forward so that her thighs were straddling my balls and cock.
“Relax, honey,” she said, pressing down my bottom so that I was resting on her thighs. “I’m going to take care of you.”
After some more teasing, Danielle took my cheeks firmly in her hands and drew them apart. Then her tongue began delicately probing my asshole.
I let out a long moan at a pleasure like none I had ever experienced. I nearly bit my lip trying to control my vocalizations, but I could not help but continue to moan like a little girl as Danielle tongued my asshole. Nor could I contain my hips bucking under her ministrations and raising myself up to offer my ass to her. My own legs drew up against her bottom as if to pull her deeper into me.
“Mm, somebody has a little clit in their ass, don’t they?” she commented. “Would you like to turn over?”
As much as I wanted the anal pleasure to continue, I was also by now desperate to orgasm. Danielle dismounted from the table as I turned over, then resumed her station kneeling between my legs.
She took hold of my cock and pulled it straight to the ceiling. She began teasing the tip of my cock with her tongue. Her free hand reached under me and began probing my asshole. I could not help but moan and gyrate in ecstasy. At the same moment she took all of my cock in her mouth and throat, she slid a finger into my willing asshole. I had just enough time to warn that I was about to come, but as she had months before, Danielle stayed on my cock. Indeed, this time, she swallowed my seed, sucking on my cock while pumping my asshole vigorously with her finger.
When my spasms began to abate, I collapsed spent on the table. Easing her finger from my ass, Danielle crawled on top of me and began kissing my neck.
“Feel good, daddy?” she asked.
“Incredible. There aren’t any words.”
I could feel Danielle’s own cock hard inside her panties. I began to reach for it, thinking I should at least try to reciprocate in some way. But, she grabbed my wrist. “That’s okay, daddy. Don’t worry about that tonight.”
We laid there for a long time until Danielle said that she was supposed to meet some friends. We had not discussed money, so when I was dressed I left the rate I had paid her before with a generous tip on the edge of the table. She had put on a short, silky robe and slippers and was waiting for me by the door.
“Thank you so much, daddy,” she said, kissing me on the lips. I could not resist grabbing her waist, and we began kissing passionately. When I leaned down to kiss her neck, she finally pushed me gently away.
“Save it, daddy. You’ll come see me again.”
“Of course. Of course. I think I’ll be seeing you tonight in my dreams.”
“So sweet,” she said, tweaking my balls gently through my trousers and giving me a last peck on the lips.
***
It was a struggle to wait a few days to call her again, and after our third meeting, we set up a regular weekly “date” at her apartment. The sessions were delightful variations of that first evening in her apartment. Danielle seemed to delight in anal play – as did I – first using multiple fingers, then a small dildo to probe my ass while I was on my back, flat on my stomach, or with my ass in the air. As much as I enjoyed our physical intimacy, I also found myself savoring her company. It was fun getting to know a bright, young person who was coming to learn their own mind and about the world. Furthermore, given her own experiences, Danielle was remarkably open-minded, and I found myself sharing things with her I really discussed with no one else.
I always tried to bring her some sort of gift. One night, I showed up with the latest book by an author I knew she liked, and Danielle seemed particularly delighted as she went to her bedroom. Danielle came out of her bedroom typically resplendent in a garter, stockings, and panties. As I undressed, I could not help but notice a second pair of black stockings draped over the back of the sofa. Danielle usually kept her apartment meticulously neat. She noticed me look at the stockings.
“Yeah, about those,” she said. “How would you feel about wearing them tonight? It’d be a really big turn on for me.”
My swelling cock began to agree before I could even get out the words of acquiescence. The silky fabric felt wonderful against my legs as I rolled on the stockings. I laid down on the table with my cock already thick with anticipation.
The session began much as the others in her apartment had. But, that night, Danielle seemed extra intent on lavishing attention on my asshole. She kept me flat on my stomach with my legs spread wide, licking and swirling her tongue against my hole for what seemed like an hour. It was heavenly. Eventually she laid down on her own stomach between my legs while continuing her attentions. For a few moments, I wondered whether this was thanks for the book. But, it became harder, then impossible, to think of anything but the intense pleasure Danielle was providing. Even my customary appreciative moaning abated as I slipped into a trance-like state of bliss.
So complete was my rapture I barely registered when Danielle stopped her oral love. I was vaguely conscious of her crawling up the table. Her hard, panty-bound cock against my buttocks, her lips to my ears.
“Can I fuck you, daddy?” she breathed into my ear, a pleading edge in her voice I had never heard before.
“Of course, baby. Please.”
I was only vaguely conscious of Danielle bounding off the table and wiggling excitedly out of her undergarments. In a flash she was back between my thighs, on her knees, rubbing oil deep into my ass. She was soon finger fucking my asshole, as she had many times before. When she slid in a second finger, I bit my lip, and still keeping me flat on the table, she eased my left leg up into a bent position. She resumed pumping, but her fingers soon gave way to a dildo she had been using in our sessions.
Abruptly the pumping stopped. From the corner of my barely opened eye, I saw Danielle raise herself as tall as she could on her knees. Her long, thin cock rigid against her torso. I could see how anxious she was fumbling to open the condom, then to unroll it on her cock, gleaming in the low light. She lowered herself to me and removed the dildo. I felt her cock between my cheeks, then with only the slightest twinge, she was inside me.
Danielle laid herself across my back and put her cheek to the nape of my neck. “Oh, daddy, you feel so good,” she said.
“So do you, baby,” I muttered.
“I’ve waited so long for this night.”
Lifting herself on her arms, Danielle began thrusting herself into me. She picked up the pace quickly in her excitement, but I could feel her restraining herself. I wanted to encourage her and her pleasure.
“It’s okay, baby. Fill me up,” I said. “Give me your hot load.”
“OH, FUCK,” Danielle cried, as she began to slam harder into me, impaling me on her beautiful cock. The savage fucking caused some discomfort, but I could tell it would not last long. Danielle just kept muttering, “Oh, fuck, oh, fuck,” as she pounded my ass, and I could feel her whole body quivering with excitement. The sensation was contagious, and I could feel the excitement rising in my own member, being vigorously rubbed against the table by Danielle’s thrusts.
At last, Danielle let out a long, “YESSSS,” as she stopped pumping and collapsed onto my back. I could feel her cock twitching in my ass and my own member responded in kind. We lay like that for a long time. When Danielle finally roused herself, she took me by the hand and led me to the bedroom, where we both fell into a deep sleep.
***
Danielle and I have been together since that night. I take her where she wants, buy her what she needs. She has cut back on her work as a masseuse, and I would like her to quit all together, move in with me, let me take care of her. We spend almost every night together anyway. And those nights just seem to grow more ecstatic as she pushes my boundaries. The stockings were just the beginning of our sartorial experimentations. And, I recently bought Danielle a very flashy gentleman’s suit she likes to wear. Perhaps someday soon, I will be the one out on her arm for the night.