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A New Makeover

"After his recent divorce, Mike embarks on a new lifestyle."

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About 6 months ago, my wife asked for a divorce. I think the exact words were, “Mike, I am feeling neglected, and my emotional needs are not being satisfied.” I’m almost sure that was a line she picked up from a women’s magazine or a psychology article. The truth was, that was the same time I was going through prostate cancer treatments, and we failed to have sex. I later found out the nights out with the girls were with another guy.

I know some of this might be my fault. With my 40th birthday coming up, I guess I’m having a mid-life crisis. I always thought a mid-life crisis meant buying a Porsche, but for me, it just means buying reading glasses in bulk from Amazon.

One of my best friends is Brent. He usually has a practical way of looking at things, and I really value his advice. We met years ago, before he told me he was gay. At first, I was a little uncomfortable, but it never affected our friendship. Back then, I was married and probably wouldn’t have spent much time with gay people. Brent showed me I was wrong. He made me realize that being gay isn’t something people talk about all the time, just like I wouldn’t go around saying, “Hey, my wife and I had sex last night.”

Brent and I both belong to the same golf club. Sometimes we meet for drinks after work to catch up, and it’s a nice, private place to unwind after a busy week. We have a lot in common, and when we’re out together, people often ask if we’re brothers.

A few weeks ago, our golf club held an event, and Brent and I teamed up. As most golfers know, after a few holes, the pace slows down, and you end up waiting to tee off.

Brent says to me, “I saw Amy with her new husband yesterday.”

“Alive?” We both got a chuckle out of that one.

After the divorce, I felt like I’d been set free from a prison. Maybe I was partly to blame. I took her for granted, and we never really talked.

“She was pregnant, Mike.”

That explained a few things. We never had kids. I was always traveling for work after six years of college, and the cancer treatments caused erectile dysfunction. I thank God that didn’t last forever.

“Mike, don’t take this the wrong way, but honestly, you’re a good-looking guy. You’re smart and successful, but you’ve let yourself go since the divorce. You look like you need a shave, and it seems like every day is Casual Friday now.”

After a short pause, I could tell Brent was worried I might take it the wrong way, but sometimes the truth stings.

“Brent, I have a question for you, and you’re the perfect person to give me an honest answer.”

“So, what is it?”

“I went to the casino the other night, just for dinner. They have a nice restaurant bar there. It’s a good spot for single people—quiet and discreet.”

“Yes, remember we went there once.”

“Oh right, I forgot you were the one who first took me there.”

"I was almost finished eating when a beautiful woman took a seat next to me and introduced herself. We started talking about relationships, and I complimented her on her legs and her outfit. We held hands, and she ran her hands up my leg, so I thought things were going well. Then she leaned in and whispered in my ear that she was transgender."

“So? What’s the problem?”

"I’m too shy about that. I told her I’m straight and have never been with a trans girl before. We exchanged telephone numbers, and she went on her way.  But the weird thing is, Brent, I’ve been fantasizing about being with her ever since.”

Later at the bar, after a few drinks, we started talking about relationships. Brent asked if I had ever thought about living out my fantasy.

"I don't think that will ever happen," I said. "How could it?"

I told Brent that after I met this girl, I’ve been perusing the internet, looking at trans girls, and I’m fascinated. In fact, it’s a fondness, and ever since, I’ve had this desire to be with a transgender girl sexually. I even had a dream about Brent and me being together.  Again, my thoughts were: Am I gay?

"Well, why not," he said. "You should at least try it once to get it out of your system. You said you think about it frequently, so why haven't you thought of at least trying to meet someone?"

"I wouldn't have a clue how to do that. I've been back to the bar at the casino twice to see if she was there, and I can't just go to a gay bar! What if someone that I knew saw me? I'm not even gay, and I would be labeled as such, no offense to you, Brent.”

"That's not what I meant," Brent said. "I can help you if you want it to be discreet. I happen to know a girl who gives erotic massages. She's gay, extremely nice, very attractive, and she lets some of her clients touch her as she gives the massage. All you have to do is set aside about 90 minutes, and you can at least try it. If you don't want to do anything, the worst you will come away with is a good massage or be out a few bucks."

"I don't know," I said. "What if I don't find her attractive? And what do you mean by erotic? What does she do?"

"Mike, all she will do is give you a massage. She explains everything before you start, and you are free to walk at any time. If you don't want to be touched erotically, just let her know. She will let you know if you can touch her. It's as simple as that. Here is a picture of the girl. Her name is Stephanie. I'll even call for you to set up the appointment."

I took the picture. OMG, Brent, I know her. I used to go to her salon until my wife was too jealous. “I would have never guessed in all my life she was a transgender girl, although I was a little suspicious that Brent carried her picture around with him.

Stephanie was in jeans with no shirt or socks. I must say, for a transgender person, she actually was pretty attractive. She had large breasts with smaller-than-average nipples like my own.

As I looked at the picture, I realized that this was probably my only chance to get this out of my system. Stephanie was good-looking, and I didn't have to do anything if I didn't want to. It seemed easy enough. It's just a massage.

"OK," I said. "Make the call.  I can reschedule anything that might come along.”

Brent called me early in the week and told me Stephanie would work me into her schedule Saturday afternoon, around closing time. Brent said to dress casually, and Stephanie would take care of me. "And don't worry! he said. It seems Stephanie already remembers you and is excited to help.”

All week I was in turmoil. Could I really go through with this? I tried to keep myself calm and not think about it, but as Friday night came, I began to think of my fantasies again, and the anxiety was high. I went to the gym to get my mind off it.

Saturday came in a hurry; I played a round of golf with some friends in the morning.

Between the golf and the gym, I was a little stiff and sore, and I was looking forward to the massage. I needed a shower, a shave, and a haircut; the shower and shave were easy, but I needed help with the haircut.

I stood up and looked at myself in the mirror. Yes, I needed some help, some professional help. I climbed into the shower and thought through my options.

For the previous 5 years, when I had time and planned, I saw Stephanie, a hairdresser who was one of the sweetest people I'd ever met and always made me feel welcome and comfortable. I was one of her first customers when she opened her salon; by chance, I saw her sign on the second day after she opened, and I needed a haircut.

I'm not the most chatty person, but somehow Stephanie and I always ended up talking about anything and everything whenever I was there. She knew almost my whole life story (I got the feeling that she thought I should've left Amy years ago), and I knew a lot about her. She was in her late twenties, came from a small town, and had moved to the city to go to school. She clearly had talent because she then worked for a few years at two of the classiest salons in the city.

I still found it hard to believe when I looked at her and talked to her. I find it hard to think anyone could guess without knowing. To my eye, she is one of the sexiest women I've ever met, tall with long legs and an athletically slim build with nice-sized breasts perfectly suited to her body type.

She had wildly changing hair colors and styles, wore classy, sexy outfits that accentuated her femininity and strength, and she walked with a self-assured yet sensual grace. Plus, she was relentlessly flirty, which always boosted my ego. Thinking about it, it was no wonder I liked going to her to get my hair cut. I wasn't her typical customer, but I'd been coming longer than most, and she liked the variety I provided compared to the rich, older female clients she usually had. A few times, when she didn't have an appointment after me, she had invited me to stay and visit with her afterward, so I was pretty sure that she genuinely liked me. The problem was that she was such a good stylist that you needed to book well ahead.

After I got out of the shower, I called her to confirm she could fit me in. Of course it went to voicemail; she mostly worked on her own, although she sometimes had guest specialists in pedicures or massage to work out of her shop for a time. She was probably busy with another customer, so I left her a message.

"Hi Stephanie, it's Michael Duncan, the one with the brown hair and the left ear scar. I've been going through some stuff the last few weeks and haven't taken great care of myself. My friend Brent called you last week.

Stephanie always teased me about the strange star-shaped scar on my ear from an accident when I was a kid, so I knew she would know who I was. It wasn't an obvious scar unless you were looking right at it, but a hairdresser would notice.

My voice tone had cracked a bit when I said, "I've been going through some stuff."

Honestly, she could charge me whatever she wanted; I knew I'd feel good seeing her and better about myself afterward. I'd pay a premium for that right now. I also knew she would be safe and understanding, and I could talk about the breakup with her more than with any of my family or friends.

Stephanie called me back. "Oh Mikey," she said when I answered (I didn't let anyone else call me Mikey, but somehow I couldn't ask Stephanie not to). "Honey, I’m running behind, but my dinner date tonight canceled on me, so why don't you come at 5:00 after I close? I'll take care of you, baby. What do you need? Just a haircut? Haircut and shave? Full spa treatment? Probably you should just put yourself in my hands and have me take care of you."

"Stephanie, that's so great of you. I wouldn't normally want to impose, but I'm in a tough spot and could really benefit from your help. I'll take whatever you can give me, but I really want to just put myself in your hands for whatever you think I need. How about I order dinner? I could get something from that sushi place around the corner or the Italian place on 10th or whatever you want. Really, anything you want."

"Ooh, don't tempt me, Mikey," she said, suddenly in a very sultry voice. "Well, since you offered, I'd love Japanese tonight, and if we eat here, that will give me more time to take care of you. Be here by 5:30; I'll take a look at you and see what you need."

She had a nice sitting area with a table off to the side in her salon where we could eat; she sometimes had friends hanging around, or customers waiting their turn, sipping tea or coffee and eating biscuits or snacks she provided.

I thanked Stephanie profusely and got off the phone feeling better than I had in months. In my good mood, I looked around my house and realized I had work to do to get it back in shape; it was a pigsty. I first spent some time ordering dinner, racking up a huge bill by picking too much of the best food for delivery. I didn't want to disappoint Stephanie. Then I busied myself cleaning up my personal disaster of a home, and somehow the afternoon flew by.

All that cleaning was hard work and, as it got closer to 5:00, I realized I had been sweating out a lot of booze. I had the scent of a cross between a bag of used workout gear and a 100-year-old pub, so I climbed back into the shower and scrubbed myself hard to get rid of the smell.

I eventually emerged smelling... decent. Better, much better. I quickly shaved and got ready to leave.

By 5:15, I was outside the salon, and I walked up just as Stephanie's last customer was leaving: a middle-aged woman in an expensive-looking outfit with outrageously styled hair. I could only assume that Stephanie made a killing from clients like this. She looked down her nose at me; she probably thought I was the cleaner, but I nodded respectfully as we passed each other and then reached for the door. Before I could grab the handle, Stephanie was pushing the door open. I stayed on the salon doorstep as she stood in the doorway and looked down towards me, appraising my appearance.

Stephanie looked as impressive as always, in black pants, baggy in the legs. Still, tight across the hips and thighs, a shimmery blouse with elbow-length sleeves that was cut long on the sides and back but held together in the front by a single button across her breasts so you could catch an eyeful of cleavage above and a glimpse of her pierced belly button below. Her hair was braided and fell over her shoulders, and she wore large golden hoop earrings.

"Oh Mikey," she said, shaking her head and backing into the salon. "Come in, come in."

I stepped in and was instantly surrounded in an unexpected embrace as the door slid closed behind me.

"I heard that snake Amy walked out on you. I'm sorry."

A rush went through me as if you might cry, but being manly, I acted like it didn’t affect me, but I enjoyed the feeling of her strong body and her strong embrace.

Stephanie was an inch or two taller than me, so being hugged by her seemed like I was wrapped in a warm shelter. I had never touched Stephanie like this, and it was an intense experience, both somehow erotic and somehow comforting.

'Thanks, Stephanie," I replied, holding on to her with my head buried in her shoulder. I let out a huge breath and then breathed in her sweet smell, not wanting this hug to end.

Finally, she released me and held me at arm’s length, looking me up and down. "It looks like you tried to shave before coming, but you'll need a touch-up, and that hair really needs some work. Let's get those out of the way and then finish with a special 'Stephie' treatment."

She locked the door and closed the blinds on the windows as I walked in. She first washed my hair, one of my favorite parts of the visit to her salon; the sensual feeling of someone's hands massaging my head always helped me to relax.

Then she brought me to the stylist's chair and began the haircut. We spent the next half an hour chatting about everything except my failed marriage, and I grew more relaxed with every minute.

‘Steph’ got busy with my hair, fussing around while flirting outrageously and making me laugh almost every minute. Finally, she stopped and spun the chair around so we were both looking at me in the mirror.

"Damn, Mikey, you look pretty sexy now. A big improvement."

Aside from the bags under my eyes, I looked like my old self. I was a decent-looking-enough guy for my age (mid-40s), but ‘Steph’ had worked wonders with a modest but stylish haircut. The three weeks of drinking had melted a bit of my belly fat. Even the bags under my eyes seemed to have faded.

"Flattery will get you everywhere, Stephanie. Even if it's untrue."

"Oh, it's true. I like my men well-groomed and with some salt and pepper. And vulnerable," she said, leering at me. "Just my type." She leaned across me as she said this, stretching forth and running her hands along my jaw.

I suddenly flushed; somehow this felt like she was taking the flirting up a notch or two, like she actually was hitting on me and not just flirting for fun. I liked it and looked at her in a whole new way while I realized I was getting aroused.

"Let's tidy up that shaving job of yours."

She tucked a towel into my collar, then picked up a bottle of shaving cream and began applying it to my face and neck. This felt different from the haircut I'd had. More trust is involved when someone else slides a razor over your neck. It felt more intimate, putting yourself in someone else's power.

She was nearly done when there was a knock on the door. "Dinner," I said, trying to get up from the chair.

Stephanie put her hand on my chest and pushed me back down. "I'll get it."

She brought the food in and put it on the table. “Mikey, just how many people were you expecting? Because there was so much food."

"I wanted to be sure that there was enough," I sheepishly replied.

‘Steph’ smiled at me and came back over to finish the shave. After a few more passes with the razor, she was done, and she warmed up a small towel under the tap to clean me up.

The warm cloth on my face was incredibly soothing, and having it held there by a beautiful woman's hands made it even better.

She then shifted, holding it with one hand and running the other over my hair, face, and neck. The feeling of her hands on my neck and face became more sensual as she held the cloth with one hand and ran the fingers of her other hand along one side of my neck and played with my ear, before sliding her hand to rest on my chest.

"Let's eat," she uttered softly in my ear in an alluring voice.

I watched her as she spun away and walked over to the table, enjoying looking at her swaying body, her languid grace swinging her beautiful athletic ass side to side. I had to quickly get up and adjust my pants to hide the sudden erection pushing against my jeans before she saw it.

I followed her across the room, sat on the couch, and began opening the takeout cartons. Stephanie put the kettle on for tea, then sat down and asked me to explain what I'd ordered.

We sat next to each other, me on the edge of the couch, turned slightly toward her, our knees touching. I picked up some chopsticks and went through the food, describing each one. Once I had finished, she pointed at a sushi roll closest to her and told me that she wanted to try that one, without making a move to pick up any chopsticks.

I was a bit confused and looked at her, but she just smiled at me, still not picking up her own chopsticks. I hesitated, then picked up a piece and raised it toward her. She opened her mouth and leaned forward slightly. I stretched out and gently placed the sushi in her mouth. She closed her mouth and began to chew, staring into my eyes the entire time.

"Delicious," she said once she had swallowed it, licking her lips and reaching to pat my knee. "Another, please."

For some reason, I found this incredibly sensual. I don't know if it was from suddenly being subservient to her, or the intimacy of feeding someone else, or the strong sexual attraction I was feeling towards her. It was probably all three combined.

I nervously fumbled my chopsticks before reaching for another piece and again raising it to her lips, watching with aroused fascination as she ate it. She thanked me and patted my leg again, this time on my thigh.

This is how dinner went: Stephanie pointed to what she wanted without putting a single piece of food into her own mouth, yet I found myself more than happy to feed her. After each mouthful, she would thank me and pat my leg, eventually leaving her hand placed on my thigh, distractingly close to my crotch.

After a little while, she told me to eat and got up to make the tea while I had a few bites. I looked at her sexy body as she walked to the kettle. She came back with the teapot and cups, and we resumed eating, me feeding her a bite before eating a bite or two myself. I had never found eating to be a sensual activity, but I sure was aroused by how tonight's dinner was going.

We chatted some more and finally talked about Amy. “Mikey, I hesitated telling you about Amy’s infidelity about a year ago. When I decided to tell you, you stopped coming in to see me.”

‘Steph’ made it clear that she thought I was better off without her and began to list things that had happened in our marriage, things that portrayed Amy in an unflattering light, many I had forgotten.

Eventually Stephanie stopped. "Enough about why you're better off without her. You need to move on. Are you going to put yourself out there? You're a handsome, eligible bachelor now."

“Mikey, you need to release some of that pent-up tension," again, patting my thigh and grinning at me suggestively.

I stammered in reply, "Oh god, I don't know. I wouldn't have the faintest clue how to go about doing that."

"That's fair," she replied. "Ease yourself into it. But be ready. You never know; someone might appear when you aren't looking. Mikey, did you know Brent confessed to me he was attracted to you?”

“'Steph', he is a friend, although the thought just crossed my mind recently.” I then explained the trans-girl fixation might be the reason.

Luckily, Stephanie stood up and told me she had eaten enough dinner, and that I needed another hair rinse before the spa treatment. I stood, trying to hide my bulging crotch, but Stephanie clearly could see what was going on in my pants and grinned.

I quickly sat down at the hair wash station. This time, she insisted I take my shirt off so it wouldn't get wet, which didn't make much sense since it hadn't gotten wet the first time, but she was in charge, so I followed her direction. Again, the relaxation of a gentle scalp massage put me at ease, even though there was a lot of sexual tension lingering during this one.

When she finished the hair wash, I stood up and followed her into the back room. In here, the lights were dim and red; a small oval hot tub bubbled away in a tiled area to the right, and a massage table sat in front of a large wall of mirrors to the left.

"OK. Strip and get into the hot tub," Stephanie said, turning away from me.

I stood slack-jawed. "Strip? Like, naked?"

She looked over her shoulder at me. "Of course, unless you brought a swimsuit. You need to relax. A soak in here and a massage will really help you. You said that you were going to put yourself into my hands, so trust me."

She laughed, "Don't worry, I'll give you your privacy to undress," and she turned her head.

I quickly pulled my clothes off, so quickly that my erection loudly slapped off of my stomach when I pulled my pants and underwear off. I don't think I'd been this hard in years, and I was torn between wanting to hide my arousal in embarrassment and wanting Stephanie to see what she was doing to me.

I chose hiding, of course, and slid inside the water, the bubbles from the jets concealing my arousal.

Stephanie turned after hearing me get into the water. "Excellent. Now relax, I'm going to give you a neck and shoulder rub while you sit in there."

She did just that, sitting on a chair behind me and gently rubbing me with scented oil. Between the soak, the massage, the mild music, and the scented oils, I was in a trance.

We began chatting again, Stephanie leading the conversation as usual, while she gave me a decidedly sensual head, neck, and shoulder massage. Her hands would occasionally slip down into the water and rub over my chest and nipples. This time the conversation turned more racy and, in my relaxed but aroused state, I found myself revealing a few fantasies.

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It was probably the relaxing combination of the hot tub and massage, plus how unsettled I'd been for the past 3 weeks, that made me feel free to talk about much more than I normally would.

Stephanie asked if infidelity played a role in the breakdown of my marriage. Not by me. I explained to her that the ED from cancer and that she ended up pregnant were the major contributors.

I did describe a few wild situations I had found myself in over the years that could have resulted in cheating, but didn't. Twice I had been at parties that ended in group sex, one of which seemed to include male-on-male bisexual activity.

Stephanie showed particular interest in the details of those and wanted to know why I didn't experiment when given the chance. She asked plenty of questions about what I found arousing or intriguing about those situations.

Eventually, Stephanie asked what my plans were now that I was free to pursue the self-indulgent life I wanted. "What sort of experiences are you looking for?" she asked. "What kind of uncharted territory are you hoping to explore?"

I didn't even know how to respond. "I am not sure," I admitted. "I haven't really thought about it. My imagination can go wild when I let it, but Amy wasn't very adventurous, and we hadn't had sex for such a long time before she left. I admitted the fondness, almost obsession, I found in this transgender girl at the bar."

"Well, I think it's clear you've still got some drive in you," Stephanie whispered in my ear, her lips so close I could feel her breath on my neck as she swept her hands down either side of my chest and across my stomach.

This was the first direct reference to the erection I'd been unsuccessfully trying to hide for most of the evening. It had weakened while I sat in the hot tub, but it was almost instantly back when Stephanie's fingers came dangerously close.

"Oh shoot, I've gotten my shirt wet."

The elbow-length sleeves of her loose top had been submerged during her probing of my torso. I heard her moving behind me, and then she walked past me, shrugging her shirt off and heading to the sink. She dropped her shirt in the sink, then turned toward me.

"My turn for some privacy," she said, covering up her breasts with her arms. "I'm just kidding; I'm a bit of an exhibitionist. I enjoy people looking at my body," and she opened her arms. I took this as permission to stare at her beautiful breasts held in a black lacy bra as she walked towards me. Whoever did the surgery was an artist, I thought to myself. The removal of her top also exposed her stunning, smooth stomach and the lines of the spaghetti-thin bands of her panties poking over her hips above her pants. I felt like I was panting with desire as I looked at her. I think she must have been feeling something too because, for the first time, I was pretty sure I could see a bulge in her pants.

"Wow," I mumbled. "You are about the sexiest thing I’ve seen in a decade; even your femininity is striking."

"So sweet," she said, kneeling next to the hot tub. She placed her hand on my cheek and pulled my face away from staring at her body to stare into her eyes. Then she leaned down towards me, her lips parting. I leaned forward, and we kissed, delicately at first but with increasing passion, her tongue sliding inside my mouth and her hand sliding around my neck to pull my head into her. Eventually her hand gently grabbed my hair, and she pulled me back, still looking into my eyes.

"This is getting downright improper," she said with a predatory smile. "Good thing it's not during working hours, so that we can avoid interruptions. I'm going to join you in the hot tub."

She then turned away from me and peeled her pants down, exposing the black panties and her gorgeous ass as she bent over to pull her pants over her feet. She reached behind her back and undid her bra, turning back towards me as she did.

"You offered yourself into my hands for the night, and I'm going to take you up on that," she said as she released her tits from her bra and dropped it to the floor.

I admired her sexy breasts before my eyes inevitably moved down to her crotch. What I saw shook me to my core, in the best way possible. As she pushed her panties down, she slid her hand down the front and untucked herself, audibly sighing as she released her cock. She pushed her panties down to her ankle, and her cock bounced out, growing before my eyes. Then she stood, put her hands on her hips, and watched me as I eyed her growing cock.

"Phew, she was getting tight in there," she said. Her cock had grown so it was now parallel to the floor, pointing directly at me. God, Stephanie was beautiful. Her cock was beautiful. Before this moment, I hadn't even considered that a cock could be beautiful, but that was the most fitting description.

"It'll be a tight fit, but I think I can slide myself in there," Stephanie said as she walked towards me and climbed over the edge of the hot tub. My eyes didn't leave her cock, but I could hear the smile in her speech. The double meaning of her speech didn't escape me, even though my mind was whirling. I suddenly realized that my hand was tightly wrapped around my cock, but I didn't remember putting it there.

Stephanie's body slid below the surface until her breasts were floating across from me, and water sloshed over the edge of the tub. It was so cramped in the hot tub that my left leg was between her legs and her left between mine, almost touching my balls. She settled on the bench and then reached her left hand forward out of the water to touch my cheek as she leaned forward to resume our kiss. My desire overcame any inhibitions I had during our previous kiss, and I gently held her face in my hands as our tongues played in each other's mouths.

She broke away from the kiss and looked me in the eyes. "Mikey, honey. You gave yourself to me for the night to do whatever I thought you needed. You may not have been thinking of this when you said it, but I know what you need, and I've been waiting years for this. You can back out now if you want, but if you stay, you're mine for the night."

"Oh, I'm staying," I replied with more confidence than I knew.

Stephanie's face broke into a huge smile, and she leaned towards me for another deep kiss. Her hands dropped into the water, and she leaned on my legs as we kissed with increasing passion. We eventually broke the kiss, and Stephanie sat back, looking at me with that dazzling big smile of hers. She turned off the jets, and the water started to settle.

One funny thing I might add. I completely forgot Stephanie was transgender. I wanted to do everything I could to make her happy.

"First order of business, you need to help me relax a bit. It's been a long day, and she's been tucked away almost the whole time."

She reached underwater and grabbed my left hand, pulling it towards her and placing it on her large cock. The water was now still enough that I could see below the surface. I could watch as my hand slid up and down on that beautiful beast. Stephanie leaned her head back, spread her arms along the sides of the tub, and closed her eyes, her breath whistling out in a deep exhalation.

"That's it, Mikey. Yes. That's it."

My fingers could only just reach around her thick cock, so I brought my other hand forward and took her in both hands.

"Ah, yes. Two hands. Slow and firm. God, I've dreamed of this day."

I had also dreamed of doing this, but whenever I did, I felt ashamed for sexualizing a friend like that. Understanding that she had wanted me for so long completely changed the equation.

We stayed like this for a few minutes, Stephanie with her eyes closed as she enjoyed my attention, while I leaned forward, totally immersed in my work.

Finally, Stephanie let out a deep sigh. "Time for some soap. Hop out, get that bottle over there by the sink, and turn up the heat in here. I have plans for after the hot tub that don't involve clothing."

I did as she asked, walking across the room to turn up the heater, then grabbing the soap and walking back. Stephanie was looking hungrily at me as I came near. She slowly stood up in the hot tub and then stepped onto the bench, the water reaching just below her knees as I eased into the water.

"Soap me up," she ordered.

I complied, squirting soap into my hand and lathering up her legs. I was almost at eye level with her erection and was having trouble looking anywhere else. I tentatively reached up with one soapy hand, grabbed it, and began lathering it. After I scrubbed it for far longer than necessary, she turned away and bent down, placing one knee on the edge of the tub, her hands stretched out in front of her as she leaned along the edge.

"Now, my ass," she ordered. I complied with delight, lathering her cheeks up before running my fingers along the crack. I finally got up the courage to run my finger around her rosebud. It had been winking at me between her spread cheeks, enticing me to touch it. Stephanie moaned, so I proceeded further and pushed the tip of my finger into her, slowly sliding it in and out while fondling her balls with my other hand. She wiggled her hips, and I continued, my own cock rock hard just below the surface.

"One more finger, Mikey."

I added a second soapy finger beside the first and pushed both inside her. She moaned in response. I slowly began moving them in and out, and Stephanie arched her back even further, almost laying her upper body across the edge of the tub, arms stretched out in front of her. I continued for a little while before she stopped me.

"That's enough for now," she finally said. "Go and get the towels and dry us off."

I pulled my fingers out, gave them a quick rinse in the tub as I climbed out, and picked up a towel from the top of the massage table. I turned and watched Stephanie quickly soap up her arms and torso, including those amazing tits. She then slipped back into the water to rinse before emerging like a dream, a glorious wet vision stepping from the hot tub, water running down her strong and gorgeous body.

I moved towards her and wrapped her body in a towel and began to rub her dry. I dried her torso and arms, feeling a sensation in my body as I rubbed her firm tits.

I moved on to delicately wrap her hair in the towel and gently rubbed the ends of her long braids that had fallen into the water. I then knelt next to her and dried her legs before she turned away from me, and I paid particularly close attention to her ass. As I dried her legs, I felt her rest her hand affectionately on my head. Eventually she turned again to face me, her erection directly in front of my face, her left hand joining the right on my head.

She gently but firmly pulled my head towards her rigid cock that was pointing at the ceiling. I dropped the towel to the floor, tucked it under my knees, and then reached up to grasp her erection and pull it down level towards my mouth. I opened my lips and proceeded to put the head of her beautiful beast in my mouth. I began to suck, and Stephanie began to moan, her hands not leaving my head. I hadn't ever imagined being in this position, kneeling on the floor with a large cock in my mouth, but I was happier and more aroused than I had been in years.

With patience, I was able to fit enough of her cock in my mouth that I had to remove one hand from around its length. I moved my left hand and slid it across her stomach and up to trail along the bottom of her breasts and then slid it down and wrapped it around her hip and grabbed one ass cheek. Suddenly Stephanie pulled me up, turned me around, and bent me over the massage table. I stood against the massage table, bent at the waist, hands on the sides of the table and looking over my shoulder at Stephanie.

"I can't wait any longer, baby," she growled.

She picked up a bottle of oil and squirted it on my ass, her cock, and her hand. She was completely focused on her cock and my ass as I eyed her. God, she was beautiful, I thought.  Her defined abs flexed as she readied herself to fuck me. She rubbed my ass and then slipped an oily finger right inside me. It met almost no resistance. She pulled it out and slid 2 fingers in, again, with almost no difficulty.

"Have you had something up here before me?" she asked, finally looking up at me, peering over my shoulder.

Years ago I had tried many things with my wife to spark our sex life; I planned elaborate dates, bought porn to watch together, bought lingerie and toys (including some anal toys).

Amy hadn't been interested in anything beyond the dinner dates, and particularly not the anal toys. She'd told me to throw them away, but I kept them in the slim hope that she would change her mind and want to try it someday.

That day never came, but as sex between us became more and more rare, I found myself watching more and more porn. Inevitably, I got into less mainstream genres and became more interested in intimate activities that I knew she would never do with me. Finally, one day I took the butt plug into the shower when she wasn't home. That eye-opening experience turned into semi-regular use, and I eventually tried the small dildo. Over time, I used it a few times a month when Amy was out of the house.

"Mikey! You wonderful little perv!" she said, slapping my ass. "Oh, that makes me so happy; maybe this won't hurt as much then. I don't really want to hurt you. Not too much, at least."

With that, she lined her thick beauty up against my tiny asshole and pushed. Well, this was very different from the much smaller silicone cock I'd had inside me a few days ago. Very different.

It started to open me up, and the pain was extreme. "Wow, Stephanie, you are way bigger than that dildo!" She was stretching me wide, painfully wide. "Oh god!" I almost shouted as the head popped past my sphincter and settled in my ass.

She stopped pushing and ran her hands gently over my back, trying to soothe me. She gently pushed between my shoulders, and I leaned over the massage table again. Suddenly it felt OK. Or just not bad. I felt full, impaled.

After a little while, I actually began to feel good, if uncomfortable. I was bent over a table and had a cock inside me, and somehow it felt right. Stephanie kept running her hands over my back and sides to help me relax. Then she began to push and the pain returned. She slowly pushed further in, paused, retreated, paused, and pushed back in even further. She retreated again, squirted more oil on her cock, and then slid back inside, even further still. I realized I was panting loudly, in love with the feeling despite the intense discomfort.

"Relax, baby, you're doing great." She stopped pushing and continued rubbing my back. I gradually adjusted to the feeling.

Finally, I felt Stephanie's hands on my hips, a further push, and then I felt her body against my ass. She was buried balls deep in my ass. Again, she ran her hands over my back and sides; the delicate touch, as relaxing as the pressure in my ass was, was disconcerting. I laid my chest and head flat on the table, breathing deeply and turning my head to the side. As I turned my head, I realized I was facing the mirror-covered wall; staring returning my gaze was a flushed and sweaty middle-aged man bent over at the waist and a goddess standing behind him with her cock deep in his ass. I looked at our reflection in wonder. At that moment Stephanie looked over and caught my eye in the mirror. Staring at me, she grinned and licked her lips.

"Honey, you just made my year, and I am going to give you the ride of your life."

With that, she backed out a bit and then slowly pushed back in again, no longer stopping between thrusts, slowly and gently pumping in and out of me, hands on my hips pulling and pushing. She started slowly, nearly gently, but the pace gradually increased. When she pushed all the way in, her long cock made me feel impossibly full; when she pulled back, leaving only the tip inside, I felt peculiarly empty.

In: feeling uncomfortable, almost painful, but right.

Out: feeling lonely, a feeling of absence, even disappointment.

Stephanie kept pumping that thick cock in and out of me, holding on to my hips. I had my arms spread wide, my hands holding on to the edge of the massage table. This table was rated for 500lbs, and I’ve never been so grateful for a piece of furniture in my entire life.

My cock had shriveled with the initial pain of Stephanie's beast invading my ass, but now pleasure had become the dominant feeling, and it had grown hard again. Stephanie's thrusts began making it bump against the edge of the table I was bent over.

I pulled my arms in close to my sides to brace myself and push back to give my cock enough room so it didn't feel like I was trying to penetrate the table. Stephanie must have decided my bent arms were useful handles, so she grabbed my elbows and pulled me up until I was standing slightly bent, my back arched. I turned my head to look at us in the mirror and could see us in profile.

Stephanie was behind me, thrusting her hips into me as she held my arms. Sweat had begun to build up on her forehead and her arms, shining amid the dim red light. Her firm tits jiggled with every thrust as her cock sawed in and out of my ass.

I stood, legs flexed and slightly bent, my waist slightly bent and back arched, and my body beaming with a thin layer of sweat. My erect cock was poking out in front of me, bouncing wildly with every thrust.

Stephanie noticed me staring in the mirror, so she looked over, then smiled her beautiful, wide smile at me. We enjoyed the fucking and the view of us fucking for a few minutes before she stopped, cock deep inside me, and lay on top of me, crushing her magnificent breasts against my back. She turned my head so we could kiss. It was a tender yet passionate kiss, and I could still see us in the mirror.

I looked at the vision of this wonderful, sexy woman, naked behind me, thick cock buried balls deep in my ass, as we kissed like lovers. I guess we were lovers. I had never felt such a strange combination of sensations at the same time, all overlaid with a sense of security and comfort from someone loving me after weeks of an overwhelming feeling of abandonment.

The combination of discomfort from her anal invasion, delight and interest from the subservience I felt as Stephanie took control, the ego boost from being desired by someone as beautiful as Stephanie, and the incredible arousal at the whole situation was almost too much.

Stephanie broke the kiss and pushed me down again so I was lying flat, and then lifted my leg to rest it on the edge of the massage table. I realized that this offered her a clearer view in the mirror of her cock going into my ass. She then grabbed each of my arms and pinned them behind my back, holding them in place with one hand. She then resumed fucking me, pounding into my ass. She clearly was in control, dominant even, although it didn't feel disrespectful or degrading, just hot and satisfying.

After about 5 minutes of this, Stephanie slowed down and then slowly pulled herself from me and let go of my arms. "Lie on your back," she told me. I lay on my back, ass on the edge of the table, legs bent and spread wide. Stephanie stood between my legs, lined herself up with my ass, and slid back in. She began thrusting into me, looking down at me with clear affection and desire. I looked back up at her in lust and wonderment as she grabbed my cock and began stroking me in time to her thrusts in and out of my ass.

The tension built; I could tell she was getting close, her animal instinct and movement growing more ragged, harder, faster, her breathing deeper and faster. Her hold on my cock was so tight I felt my climax building, as watching her as she fucked me was pushing me over the edge. I began to shake and cum, shooting my load all over myself; the first shot landed on my face before I coated my chest and stomach.

Suddenly, almost frantically, Stephanie pulled out of my ass and held her thick cock as it began shooting all over me. I felt the first shot hit my tender asshole before she turned it upwards and cum started to arc up onto my stomach and chest, the last few shots landing on my cock and my balls. I lay in complete silence, watching Stephanie shake with her orgasm, before she moved back and eased herself down into the bench on the side of the hot tub.

I turned my head to look at her, and she smiled at me. "Mikey, you have no idea how long I've wanted that."

"You're right," I replied. "I had no idea you had any interest in me all these years. But, damn, I'm sure glad I found out tonight, even if my ass feels like it'll hurt for days."

She stood and picked up the towel I had used to dry her off and began wiping the cum off of us. Once she finished, she rummaged through the massage supplies under the table before emerging with a small jar. "OK, roll over. I've got some cream to help with that. Then I'll give you a rubdown; I am not done with you for the night."

I rolled over as I heard her open the jar and then felt her apply a cool cream to my tender anus.

"This is a special anal salve; the rawness should ease." After rubbing it into my ass, she wiped her hands on the towel and then began rubbing the scented oil into my sore leg muscles and my back.

I lay on the massage table and began to drift off to the sensation of her gentle attention as her hands pressed and squeezed my body. I must have fallen asleep because I woke to the clink of glasses. I looked up, and Stephanie was walking towards me with two glasses in one hand and a bottle of cognac in the other. She was still gloriously naked. She put the cognac down and handed me a glass before leaning against the massage table and taking a sip of hers. I sat up, legs hanging off the side of the massage table, and took a sip.

"Mikey, I don't think you should be alone tonight. You've been through a lot, and I think you should have someone around for company and support."

I looked at her, wondering where she was going with this.

"I only live two blocks away. Why don't you come over to my place and stay for the night? We can hang out, we can cuddle and fall asleep early, or we can have some more sexy fun."

I got the distinct impression that Stephanie had a preference. It all sounded great to me, but my cock had started stirring as soon as she suggested I stay over at her place. Stephanie noticed and smiled.

"Is that a yes to a sleepover?" She asked.

"Yes," I replied. "Although, Stephanie, you've done so much for me when I needed support and wasn't really willing to admit it. How can I repay you?"

Stephanie smiled her wide, beautiful smile. "Oh, Mikey, this isn't entirely selfless. I have been dreaming of taking your virginity for years, and you gave me that. And I want more, much more, if you're willing."

I smiled back. "Well, I think we both gained from that then. I have never had such an amazing sexual experience before. You are the most incredible and beautiful person I have ever met, and you have opened my eyes. I feel like I am in your debt just for that, let alone everything else."

She continued smiling as she leaned over to kiss me. "Well, if you insist, then I guess you owe me, and I know just how you can repay me. Get dressed, let's walk home, and then you can begin paying down your debt."

She said all of this with a smile, so I wasn't worried about what she would ask of me. I was mostly just turned on.

"Mikey, I feel this might be the beginning of a new chapter in our life."

Not The End

Published 
Written by JonPaul
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