Prostate Massage and More

I had been visiting a 'special' massage person for about a year when things got even more fun. Eve, as she called herself, had been recommended by an online friend as a local woman that offered a mindblowing prostate massage. After having the occasional girlfriend play with my ass from time to time, I had become more and more interested in experiencing real anal and prostate play. Though I had not really explored it, I guess I had a little bit of a submissive streak in me. The idea of a woman penetrating me was more than appealing but, of course, it was not something one can ask for normally.

Anyway, I finally worked up my nerve and set an appointment. She had a private massage studio in her apartment and everything was better than I could have imagined. Eve was beautiful, with long brown hair, pouty lips and a great figure. She is, I guess, around 40 or so, and is very sweet, confident and comforting. From the start, she stressed that my massage and release was the only thing on the menu. I wasn't looking for a hooker, so this was okay with me. She led me to the studio and had me get undressed. She had a thick, wide mat covered in a clean sheet on the floor. I laid down on my stomach and covered myself with a towel as she instructed. She returned to the room in a very skimpy swimsuit, explaining that she found it more enjoyable for all if she was sparingly dressed during the massage. Again, she stated that was a far as it would go with her clothes removal.

For most of the next hour, she gave me a wonderful massage, hitting all of the sore spots on my 6' frame. She had me turn over and massaged my arms, chest, legs and feet. It was obviously that I had a hard-on but I was beyond caring and she knew it came with the territory. When I was at the zenith of my relaxation and excitement, she asked if I was ready for my prostate massage. Of course, I said I was. She instructed me to lift my ass from the bed and she placed a large, firm pillow under my lower back. My actual ass was hanging off of it. As she reached over and put a glove on her right hand, she told me to relax and bring my knees up towards my chest. Through half-closed eyes, I watched her apply a generous helping of lube to her gloved fingers. At this, my cock grew harder.

Eve, again confirming that I was ready, gently pulled the towel from my body. My cock, 7" and cut, was dripping precum. Freed of the weight of the towel, it popped straight up, a strand of clear fluid spanned the distance from my cockhead to my stomach. I was more than ready for this. She told me to relax (as if that were possible) and began to rub my anus with her slick, lube-covered fingers. She circled around my hole, easing her finger in a little more with each pass. Eventually, she slid her long, middle finger into my hole, making me moan. I saw her smile at this as she enjoyed the obvious power she had over me. For a few minutes, she slowly pumped her finger in and out, letting me grow accustomed to the intrusion. Once she was convinced that I was ready, she inserted the finger deep and I felt her begin tracing circles deep inside my body. For many minutes, she probed my ass, rubbing my prostate more and more firmly. My precum was flowing and I began to moan more loudly. Feigning concern, Eve asked if I was okay.

I smiled and sighed "I'm perfect." She said to let her know if I felt any pain or discomfort. Instead I asked if I could make a request.

Smiling, she said "Within reason."

I worked up my courage and said "Can you use two fingers?"

She smiled more broadly and then I felt my asshole being stretched farther. I pushed back on her fingers as they began to fuck me, rubbing my prostate each time they plowed into my hole. I didn't know it could feel any better and then I felt her hand on my steel-hard cock. Tenderly but firmly, Eve began to stroke my dripping cock. She cooed "Okay, baby. Let it go. You have my permission. Enjoy this."

I don't know who was moving more; Eve stroking my cock and finger-fucking me or me panting and trying to fuck her hand and push against her invading fingers. Regardless, it didn't last long. I warned her I going to cum and she again gave me permission to let go. Almost screaming "FUCK ME", I shot thick streams of cum across her hand, across my stomach and chest, and even had the first or second shot hit my chin.

A small sense of pride emerged when Eve said "WOW! I've not seen a man cum that much from my massages before." I was not sure if she says this 'to all of the guys' or not but I loved it.

Eve removed the glove and then used a warm, wet towel to clean me up. She told me to relax and get dressed only when I was ready. I departed from that first appointment but knew it would not be my last. My visits went that way for many months and, over the course of a year or more, I found myself very comfortable with Eve. I still was not angling for more, though she was beautiful, sexy and incredibly erotic. During our pre- and post-massage talks, I mentioned more than once my desire to meet a girl that would be comfortable with the prostate work and more. One night, though she said she does not like to work with intoxicated clients, she did work me in late-night after a company party. On that evening, I admitted my desire to be dominated and to be fucked with a strap-on. Eve was very cool about this and said a lot of men would like that if they could open their mind and remove the 'gay' associations from it. Like I said, Eve was and is an incredibly openminded woman. I learned just how cool upon my most recent visit a couple of weeks ago.

I called to set another appointment and told her I deserved it since it would be happening on my 33rd birthday. She laughed, knowing that I never needed a 'reason' for my visits. Anyway, she said she will do her best to make sure I enjoyed my massage. I arrived late in the afternoon on my birthday and she greeted me in her robe as she sometimes does. I undressed in the studio and neatly set my clothes aside. I had long since stopped using my towel during the initial stages of my massages and Eve never seemed to mind. She said she didn't have any other clients coming that day and so she could take her time with me. The general body massage was slow and sensuous. She rubbed my neck, shoulders, arms, feet, legs and asscheeks until I felt like a relaxed blob. She had doffed her robe and was in an extra-small bikini this time. Her nipples were hard and it was driving me crazy. As always, my cock was dripping as soon as she had me turn over.

After a long, slow massage of my chest, arms and legs (always avoiding my obvious hard cock), she said she had a one-time birthday surprise for me. Curious (and genuinely touched), I asked what it was. She said to close my eyes and not to open them. The stern way she said this made me more curious and, with my stated desire to be controlled by a woman, excited. I closed my eyes tight, wondering what this could possibly be. I could hear her moving around the studio but had no idea what was in store.

She said to keep my eyes closed and then I felt her gently grasping my hips as she normally did to make me lift up for the pillow that went under my lower back. Still in the dark, I lifted my hips and indeed felt the pillow going beneath me. The thick mat moved as she positioned herself between my legs. I had pulled my knees up as I normally did but, strangely, I felt the top of Eve's thighs on the bottom of mine. None of the the other massages had ever had this kind of body contact, so I was dying to know what the deal was. Following orders though, I didn't peek.

Anyway, I was there, eyes closed, laying on my back with my legs pulled up, Eve's legs in firm contact with mine...then I felt something hard, thick, slick and heavy fall against my erect cock. Before I could think about it, I opened my eyes and looked down. Eve was between my spread legs, 'standing' on her knees. Her bikini was still on but she was also wearing a strap-on cock. Her dick was wrapped in a condom and greased up with lube. A smile was on her face but a question seemed to be in her eyes. She said "I know you have hinted about this from time to time and, with it being your birthday, I couldn't resist. I have no problem using this mechanical substitute for your prostate massage today but you know the rules." Being so near to my most hidden desires, I would have agreed to anything.

The cock was probably 8" long and thick. "Tell me at any time if you feel real pain or you need me to stop. I can always perform your massage as I normally do."

I told her not to worry about it but to please go slow. This request implied that I was worried about the size but, if I have to be honest, I wanted this to last as long as possible. She pulled back a little, leaving my own cock sticky and slick with the lube from the fake cock. I moaned as I felt the head at my asshole. She told me to push out as if I was trying to use the bathroom. Strangely, this allowed the head of the real-looking cock to pop inside of me pretty easily. I moaned and then panted "YES". She laughed. Eve, after a moment or two for me to get used to the intruder, began to slide her member into me. I again asked that she go slow though I think she knew that this time I was trying to drag this out. Eventually, I was asking her to go faster though. "Eve, please fuck me. HARDER!" I couldn't help myself. Though I had not touched my own cock, it was dripping an ever-increasing stream of precum onto my stomach.

Going with this unique set of events, Eve got into her part as well. "You like this, don't you? Having me fuck your ass? SAY IT!" Of course I loved it and agreed with anything she demanded of me. At one point I recall asking if I could turn over and she allowed it. Once I was on all fours, she fucked me with hard, long strokes. I reached down to feel my own cock and Eve demanded "DON'T TOUCH YOURSELF!" I, of course, obeyed.

All good things must come to an end and my first strap-on experience had to as well. I was on my back again, my legs now on Eve's shoulders. This allowed her to plow into me more deeply than at any other time. She was sweating and, at times, enjoying the fucking as much as I was (or I want to think so at least). "Beg me to cum."

It was a simple command and one that I was more than happy to oblige. "Please, Eve, let me cum. Please stroke my cock. I'll do anything if you will let me shoot."

Eve buried her cock deep in my ass and grabbed my cock. With a firm hand, she stroked my dick and I was screaming and shooting within a minute. The amount of cum, shooting all over my stomach and chest was incredible. I have NEVER cum so much. It was everywhere, including all over Eve's fist that was still encircling my cock. The dildo was still deep inside me and I was still putty in her hands. "You enjoyed having my cock inside you?"

I moaned that I did and that I loved being in her control. Before thinking, I added "I loved being your little bitch."

Eve laughed as she removed her cum-covered hand from my still-hard cock. Still panting with eyes closed, I was surprised when I felt something slick on my lips. My eyes flew open and I saw, and tasted, Eve's fingers. "You made a mess and should clean it up." Shocked but excited yet again, my mouth opened and allowed her cum-dripping fingers into my mouth. "Good boy" was all she said, again and again.

I dutifully cleaned her fingers and, once that was complete, she pulled her cock from my now sore asshole. Eve removed the condom from her prick and then used her cockhead to push the cum on my hairless chest into a pool. Getting as much of my cum on the dildo as she could, Eve brought her cock to my lips. Without a moment's hesitation, my lips parted and her cock entered my mouth. Again and again she did this until my cum was nearly gone from my chest and body. At the last insertion, she grasp the back of my head, pulling me towards her crotch, burying her dick deep in my mouth. I had never deep-throated a cock before but, gags and all, I did that day.

Finally, she pulled the member from my mouth. "Good boy. You can get dressed when you want to." Eve stood up and put on her robe as she walked out. Once my breathing had returned to normal, I pulled on my clothes. Eve returned to the studio, covered in her robe. I knew I still had a hard cock but there was no hint of hers under the robe. "Happy birthday. I hope this was the right thing to do today but please know that this was a one-time thing. If you make another appointment, and I hope you do, it will be business as usual."

I told her I totally understood and will certainly be back. I thanked her profusely and tipped her more than I normally did. When I got home that night, I replayed every moment over in my mind. As I stroked my aching cock, I thought about it all. I even played with my asshole, sliding a finger inside me. When I found myself getting closer to cumming, an idea crossed my mind. I slid down the bed a little and flipped my legs over my head, bracing them on the bed's headboard. Like this, I was able to aim my spurting cock at my face. I could still finger my asshole in this position as well. I've cum that way a few times over the last week or two since my birthday. I hope I get another present from Eve next year but, even if I don't, I have the memories.

True story.