. Prostate massage and more
I was visiting a “special” massage 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 who offered an amazing prostate massage. After the occasional girlfriend played with my ass from time to time, I had become more and more interested in experiencing real anal and prostate play. Although I didn’t really explore it, I think I had a bit of submission in me. The idea of a woman penetrating me was more than appealing, but of course it wasn’t something one would normally ask for.
Anyway, I finally calmed my nerves and set up a date. 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, luscious lips and a great figure. I think she is in her late 40’s and very sweet, confident and comforting. From the start, she emphasized that massage and my release were the only things on the menu. I wasn’t looking for a hooker, so that was fine with me. He led me to the studio and made me undress. There was a thick wide mat covered with a clean sheet on the floor. I lay on my stomach and covered myself with a towel as she told me. She returned to the room in a skimpy bathing suit, explaining that she thought it was more pleasant for everyone if she was scantily clad during the massage.
For the better part of the next hour, she gave me a wonderful massage, hitting all the sore spots on my body. He made me turn around and massaged my arms, chest, legs and soles. It was obvious I had a problem, but I was beyond worried and she knew it came with the territory. When I was at the height of my relaxation and excitement, shem-a asked if I was ready for my prostate massage. Of course I said I was. He told me to lift my bottom off the bed and placed a big firm pillow under my back. My ass was hanging on her. As he reached down and placed a glove on his right hand, he told me to relax and bring my knees up to my chest. Eyes half closed, I watched her apply a generous helping of lube to her gloved fingers. At that, my penis grew bigger.
Eve, confirming again that I was ready, gently pulled the towel off my body. My penis was dripping with semen. Released from the weight of the towel, it appeared straight up, a stream of clear liquid spanning the distance from the head of his penis to his abdomen. I was more than ready for it. She told me to relax (as if that was possible) and started rubbing my anus with her soft lube covered fingers. She circled around my hole, inserting her finger a little more with each pass. Finally, he slid his middle finger into my hole, making me moan. I saw her smile at that as she enjoyed the obvious power she had over me. For several minutes, he slowly pumped his finger in and out, letting me get used to the intrusion. Convinced I was ready, she inserted her finger deep and I felt her begin to draw circles deep inside my body. For many minutes she probed my ass, rubbing my prostate more and more firmly. My semen was flowing and I started moaning louder. Becoming concerned, Eve asked if I was okay.
I smiled and sighed:
– I’m perfect.
She said to let her know if I feel any pain or discomfort. Instead, I asked if I could make a request.
Smiling, she said:
– Within reason.
I plucked up the courage and said:
– Can you use two fingers?
She smiled wider and then I felt her stretch my ass further. I pushed his fingers back as they began to pull me, rubbing my prostate each time they entered my hole. I didn’t know it could get any better and then I felt his hand on my steel hard cock. Tenderly but firmly, Eve began to caress my dripping cock. She told me:
– OK love. Free yourself. You have my permission. Enjoy this.
I don’t know who moved more; Eve would caress my cock and rub it with her fingers or I would gasp and try to pull her hand away and push away her invading fingers. Regardless, it didn’t last long. I warned her that I was going to ejaculate and she again gave me permission to let go. Almost screaming, I shot thick streams of cum over her hand, over her abdomen and chest and even gave the first or second shot to her chin.
A small sense of pride arose as Eve said,
– WOW! I have never seen a man ejaculate so much since my massages.
I wasn’t sure if she was saying this to “all the boys” or not, but I loved it.
Eve removed the glove and then used a warm, wet towel to clean me up. He told me to relax and only get dressed when I was ready. I walked away from the first date, but I knew it wouldn’t be my last. My visits went like this for many months, and within a year or so I was very comfortable with Eve. I was still not looking for more, although she was beautiful, sexy and incredibly erotic. During our pre- and post-massage chats, I mentioned several times my desire to meet a girl who was comfortable with prostate massage and more. One night, although he said he didn’t like working with drunk customers,m-a worked late at night after a company party. That evening, I admitted my desire to be dominated and penetrated with a strap-on. Eve was very cool about it and said that a lot of men would like it if they could open their minds and remove the “gay” associations from it. As I said, Eve was and is an incredibly open-minded woman. I learned the hard way on my most recent visit a few weeks ago.
I called to set up another appointment and told him I deserved it since it would be on my 33rd birthday. She laughed, knowing I never needed a “reason” for my visits. Anyway, she said she would do her best to make sure I enjoyed the massage. I arrived late afternoon on my birthday andm-a greeted in a robe, as he sometimes does. I undressed in the studio and carefully put my clothes away. I’ve long since stopped using my towel in the early stages of my massages and Eve never seemed to mind. She said she had no other clients coming that day and she could spend her time with me. The overall body massage was slow and sensual. He rubbed my neck, shoulders, arms, legs, soles and bottom until I felt like a relaxed blob. She took off her robe and was in a very small bikini this time. Her nipples were hard and driving me crazy. As always, my cock was dripping as soon as he put me on my back.
After a long slow massage of my chest, arms and legs (always avoiding my obvious hard cock) she said she had a surprise for me. Curious (and frankly excited), I asked what it was. He told me to close my eyes and not open them. The stern way he said itm-a made more curious, and with my stated desire to be controlled by a woman,m-a excited. I closed my eyes tightly, wondering what it could be. I could hear her moving around the studio, but I had no idea what was coming next.
She told me to keep my eyes closed and then I felt her gently squeeze my hips like she normally did to make me lift the pillow she was putting under my back. Still in the dark, I lifted my hips and actually felt the pillow go under me. The thick rug moved as she positioned herself between my legs. I had pulled my knees up like I usually did, but strangely I felt the tops of Eve’s thighs against my ass. None of the other massages had ever had this kind of body contact, so I was dying to know what it was all about. Following orders, however, I did not look.
Anyway, there I was, eyes closed, lying on my back with my legs up, Eve’s legs firmly in contact with mine…then I felt something hard, thick, slippery, and heavy fall onto 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 penis was wrapped in a condom and smeared with lube. A smile was on her face, but a question seemed to be in her eyes. She said:
– I know you’ve hinted about it from time to time, and since it’s 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 close to my deepest desires, I would have agreed to anything.
The cock was probably 20 cm long and thick.
– Tell me anytime if you feel real pain or need me to stop. I can always perform your massage as I usually do.
I told him not to worry but to go slow. This request implied that I was worried about the size, but to be honest, I wanted this to last as long as possible. She pulled back a little, leaving my own cock sticky and soft with the lube from the fake cock. I moaned as I felt the head against my ass. He told me to relax as if I was trying to use the bathroom. Oddly enough, this allowed the real-looking penis head to enter me quite easily. I moaned and then gasped “YES”. She laughed. Eve, after a moment or two to get used to the intruder, began sliding her member into me. I again asked him to go slow, although I think he knew I was trying to pull this off this time. In the end, however, I asked him to go faster.
– Eve, please pull me harder!
I could not help myself. Although I hadn’t touched my own cock, an ever-increasing stream of semen was dripping down my abdomen.
Going with this unique set of events, Eve also stepped into her role.
– You like this, don’t you? Shall I put it in your ass? Say it!
Of course I liked her and agreed to whatever she asked of me. At one point I remember asking if I could come back and she allowed it. Once I was on all fours, she pulled it into me with hard, long thrusts. 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 too. I was on my back again, now my legs were on Eva’s shoulders. This allowed him to enter me deeper than ever before. He was sweating and sometimes enjoying himself as much as I was (or so I want to think).
– Ask me to ejaculate.
It was a simple order and one I was more than happy to fulfill.
– Please, Eve, let me ejaculate. Please stroke my cock. I’ll do anything if you let me shoot.
Eve buried her cock deep in my ass and grabbed my cock. With a firm hand she caressed my cock and I screamed and ejaculated within a minute. The amount of sperm that poured over my abdomen and chest was incredible. I have NEVER ejaculated so much. It was everywhere, including Eva’s fist still encircling my cock. The dildo was still deep inside me and I was still in her hands.
– Did you like having my cock inside you?
I moaned that I did and that I loved being under her control. Before thinking, I added:
– I liked being your whore.
Eve laughed as she removed her cum covered hand from my still hard cock. Still panting with my eyes closed, I was surprised when I felt something slide across my lips. My eyes opened and I saw and tasted Eve’s fingers.
– You made a mess and you should clean it up.
Shocked but excited once again, my mouth opened and allowed her dripping fingers into my mouth.
– Good boy, was all she said, over and over.
I carefully cleaned her fingers and once she was done she pulled her cock out of my now sore anus. Eve removed her condom and then used her head to push the cum down my hairless chest into a pool. Getting as much of my cum as she could onto the vibrator, Eve brought my cock to her lips. Without a moment’s hesitation, my lips parted and her cock entered my mouth. Again and again she did this until the sperm was almost gone from my chest and body. On the last insertion, she grabs the back of my head, pulling me to her feet, burying her cock deep in my mouth.
Finally she took my member out of my mouth.
– Good boy. You can dress up when you want.
Eve stood up and put on her robe as she walked out. Once my breathing returned to normal, I pulled my clothes off. Eve returned to the studio, covered in a robe. I knew I still had a hard cock, but there was no sign of her under the robe.
– Happy Birthday. I hope this was the right thing to do today, but please know that this was the only time. If you make another appointment, and I hope you do, it will be business as usual.
I told him I understood perfectly and would definitely come back. I thanked him profusely and tipped him more than I usually do. When I got home that night, I replayed every moment in my mind. As I caressed my aching cock, I thought about everything. I even played with my anus, slipping a finger inside me. As I found myself nearing ejaculation, an idea occurred to me. I slid a little on the bed and swung my legs over my head, resting them on the headboard. Thus, I was able to direct my spurting cock towards my face. I’ve ejaculated like this a few times in the last week or two since my birthday. I hope to get another gift from Eve next year, but even if I don’t, I have the memories.
