Eva

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A prostate tale.
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tailtales
tailtales
187 Followers

A little more detail than my normal tale.

I had a very sheltered life; my parents had never explained the birds and bees so my limited knowledge was from school mates. As to be expected this information was not very reliable or accurate. So when Eva became my first real girlfriend I had zero experience. We had been seeing each other for the past seven months. It took three months before we got intimate but we had been making up for lost time ever since. We were lying in her bed relaxing after a vigorous event. I love oral sex, both giving and receiving and we had spent an extra longtime practicing our skills on each other. I'm not sure but I think Eva had three very satisfying orgasms and I know I had two of them.

It was after we shared a shower and I was dressing when she asked me if I'd ever had a prostate massage. I confessed that I didn't know if I did or not. She informed me that if I didn't know then I had never had one and if I would like to try one next Friday. She could fix us dinner and later we could see what I thought about them. I might mention that Eva was five years older than me and she didn't hide the fact that I wasn't her first or second or third person she had experience with. She would sometimes say things like, 'Jake and I would or sometimes Mike liked to'. Because of my zero experience she could guide and teach me so many things.

That Friday we had a pleasant meal. Meat loaf, mashed potatoes and mixed vegies. As I helped clean up Eva asked me if I still wanted to try a prostate massage. I thought a massage can't be all bad. When I played football in high school we were offered back and leg massages they felt good, so yah I was up for a massage anytime. Oh what a surprise I had coming.

Eva was a professional massage therapist so she had a regular table and all the supplies. When she told me to strip and lay on my stomach I was quick to follow her directions. I expected her to undress also and when I asked she merely said this was all about me. Later if I was able we could see about her needs. Like a normal massage she started to rub warm oil on my back. She started on my shoulders and slowly worked her way down.

It was when she finally reached my butt that things began that was maybe not what I expected. She was spending a lot more time rubbing and squeezing my cheeks. She would use both hands and spread me open. I was worried that she could see that private place. When she held one cheek to the side and a slippery finger slid down the crack I knew was exposed. I was feeling ashamed and excited. Eva was touching me back there.

My penis was kind of hard when I first lay down and I had lifted it to point up. I didn't want her to see it if I got hard and get offended. It was a good thing I did because I was getting harder. I had to wiggle a little to give it room. She slapped one cheek then the other, not hard but enough to sting. She asked me if that felt good. I just grunted. Then she hit them again harder and asked if that was better. The third time she smacked me even harder and when I cried out so told me I should have answered the first time.

I felt her long hair touching my backside and she kissed one cheek and then the other. When she asked if I was ok I told her I was. She bit me, not mean like, more a love bit. I was realizing I was likening this massage. Enjoyable and Interesting, I never would have thought that getting spanked and kissed would be like it was. She could give me a prostate massage any time.

I sighed and started to thank her for such a good massage when she informed me that it was just starting. I was to relax and just let it happen. She spread me open again with one hand and I could feel more warm oil running down the crack and across the butt hole. Then she was touching and rubbing right there. Damn that did feel good. And then it got better.

I could feel a finger pressed against me. Then it slowly slipped inside, just a little ways. Eva asked if I was doing ok. When she wiggled her finger I told her yes, I was ok. I was disappointed when her finger was withdrawn. I was hoping she might do it a little more, actually a lot more would have been good. Being in there was nice and when she wiggled her finger it was even better.

It did get better. She poured more oil, all over my ass. She massaged and pulled and spread and spanked and just spent minutes working me over. When she asked if I was ready for more I couldn't believe there could be more. As she was running a finger up and down the crack I was ready for whatever she had in mind and told her so. She moved up and whispered in my ear that it was just starting, there was a whole lot more to come.

That finger that had been rubbing me back there was suddenly back inside me, only this time it was in deep. When she started to pull it out I was disappointed until she pushed back in. Oh it was wonderful; she was fucking me with her finger. The pleasure was unbelievable. I was humping the table, moaning and getting close to coming.

Then she pulled her finger out. I begged her to do more; I was close, so very close. She chuckled and said she knew that but she wasn't done yet, there was more. She told me to relax a minute. Hers hands were softly running across both cheeks and she softly hummed some nameless tune. From time to time a finger would slide down between my cheeks reminding me of the pleasure I felt before. More oil was applied and worked in. I could only wish she would do more. I had been so close and then denied.

I thought that Eva loved me. Here she was just some heartless bitch, tormenting me. Treating me to such pleasure and then stopping. It wasn't fair, I deserved more. She had no pattern to what she was doing. She might spank me, one - two - three times, slip a finger inside, sometimes shallow - sometimes deeper, knead my cheeks like bread dough, gently run her hands all over, a finger might slid over my nuts or worse yet nothing for over a bit. She was driving me crazy. My cock was so hard I was afraid it might bust open like an overcooked hotdog. When I would hump the table she would tell me to stop doing that.

She demanded that I get up on my knees with my shoulders down on the table. What devilish thing did she have in mind now? More oil, more rubbing, more finger teasing the opening only now my balls were out in the open and they were caressed with a slippery hand ever so gently. Then it was a finger being pushed back in as she worked the ball sack. She was slowly finger fucking me. I was in agony.

So I reached back and took ahold of my needy cock. Her finger came out and she let go of my nuggets and slapped my ass hard. With a no nonsense voice I was informed to leave that alone. If and when she decided it was time she would tell me I could touch it. The torture continued, slaps, fingering, ball play or just ignoring me for periods of time.

Then it got better. After another application of oil her finger went even deeper. Somewhere in there she found a spot that made me cry out in pleasure. She laughed and informed me she had found my prostate. Now I knew what a prostate massage was. It is, it was, the most wonderful feeling in this world. I could feel my orgasm coming. There was no stopping it. Until she pulled her finger back out and went back to massaging my butt cheeks again and running a finger up and down the crack and tickling the opening or holding my balls in the palm of her hand.

I was begging her to finish me. A giggle and she told me soon, maybe. She had one or two more ideas and I should be patient. I didn't want to wait. I wanted it now. I begged some more but she stood firm. All she would tell was that the wait would be worth it, maybe. I begged some more. I couldn't believe she could be so cruel and or I could be such a wimp, begging a woman to let me come.

When she told me to roll over on to my back I could only wonder what she had in mind for me next. The wait wasn't long. She rubbed my stomach firmly. Then she picked up my cock and moved it out of the way so she could rub me over my pubic hair. I was back to begging her to stroke me, finish me, I needed relief. Smiling she leaned over and gave me a kiss and said soon. It would soon be over just a little longer. The best is right around the corner.

She lifted my right leg and told me to hold it up. I grabbed it behind the knee and then the left leg was up in the air with me holding them both up. Then I was to spread open. In her dictator voice she wanted to be able to see everything. I watched as she poured more oil on my cock and my balls and my ass crack. She was right. The best was coming. One hand was masturbating me. The other hand was down below and a finger was gliding inside. I was being jerked off ad finger fucked. Eva warned me to tell her when it was going to happen.

I didn't need to. Even if I wanted to, I was beyond the power of speech. I could only moan. Thankfully she sensed it. A finger was massaging my prostate. She was stroking me rapidly and just before I exploded she leaned down and sucked my cock head into her mouth to swallow my explosion.

I don't think words can describe the feelings I went through. It was the most wonderful experience in my life. As her finger was pulled out, as her lips released my cock I was unable to move. My legs flopped down to the table. I just lay there so relaxed, so content. I must have fallen asleep. The satisfaction of Eva never crossed my mind. I could only breathe. The world was wonderful. I was at peace.

Someone was talking to me and pushing on my shoulder. Telling me to get up and go shower. It was after midnight and I had to go home. The shower revived me enough to remember what had happened and that I hadn't done anything to Eva and I had to. She had never even undressed. I needed to do her. It wasn't fair.

I offered, I pleaded, and I begged only to be told that all was good. As I was resting she had taken care of her needs and if I was able I should come back later the next week and we could do something. Had I ever seen a strap-on?

The end

Thanks for reading this little tale. I hope some of you enjoyed it. Comments are welcome.

tailtales
tailtales
187 Followers
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5 Comments
Dylan1Dylan13 months ago

your description was spot on. nice story. i think i need to see the back catalogue now

AnonymousAnonymous3 months ago

Pressure on that sexy little organ can be very hot..especially hot when the wife suddenly realizes it makes hubby hard..Is hubby gay?…when mine asked me that my cock suddenly jerked and cum shot out..mmmm…wifey knows all my secrets..

JT

massageguy1massageguy14 months ago

Great story...she should have used another finger

AnonymousAnonymous4 months ago

Amazing story! She absolutely needs to peg him in the next story to give him a true prostate orgasm! Can’t wait for the next chapter!

OOAAOOAA4 months ago

WOW WOW WOW... what a graphic enjoyable experience ;)

5 stars!

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