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Second Time Was A Charm
27/04/2023
I was on my way to Mary’s for her second erotic massage. Her first time was about three weeks ago and she had told me that she enjoyed herself greatly, even though she was unable to reach orgasm. She said that even when she masturbated that it took her a long time to cum.

I had given her my standard erotic massage that first time. Slowly going from a full body massage, to slipping a lubricated finger up her ass and massaging her vagina with my other hand. She had groaned and said how good it felt, but she did not cum. She did enjoy the anal stimulation though, my finger stayed up her ass for a good thirty minutes and when I pulled it out, she spent about five minutes begging for me to put it back in her, which I did, until she could finally let me stop. We finally stopped and I left, but she had not cum. I felt bad about that, and kind of felt that my aching, full balls were penance for not making her cum although she seemed less concerned about it than I was.

Now I was headed to her place for round two. I was hoping that I could do better and had resolved that even though I always advertised that no overt sex was required during the massage, that if she’d let me that I would use my mouth to help her achieve orgasm. I knew from the first experience that her vagina smelled nice and clean, and that she got nicely wet when she was stimulated.

Mary greeted me at the door and was all smiles. I think she was almost giddy with anticipation, since she knew what was coming. The first time is always one of apprehension until I establish a sense of intimacy and surrender to the sensations. After the first time, anticipation always adds to the excitement of the visit.

We began the massage and I took my time massaging her scalp, face and every inch of her body, including fingers and toes individually. She squirmed a little when I did her breasts. Mary was a lady of sixty, with a nice slender, well kept body. She had short blonde hair with gray mixed in.

Finally we got to the long anticipated part. As she lay on her stomach, I spread her ass cheeks and carefully lubed her anus with jelly lube. I then told her to take a deep breath and hold it until she felt my finger sliding up her ass, and then to exhale breathing normally.

As I slid my finger into her ass, she groaned,

“Oooohhh, I’ve been thinking about this moment for three weeks”

I replied,

“That’s a lot of anticipation, hope it feels up to the anticipation”

She just replied,

“mmmmmmmmmm”.

After a while, I slowly pulled my finger out of her ass and told her to lie on her back. As she lay down face up, I slipped my finger back into her ass and began exploring her vagina with my other hand. As she had before she lay there idly stroking my thigh as I stroked her swelling pussy lips. I had shorts on this time and I moved a little so Mary’s hand could feel the bare skin of my legs. She took the hint and slid her hand up my leg, under my shorts. She soon found a way to get under my undershorts so she could touch my penis and scrotum. I sighed at the contact.

Mary felt me swelling up because of her touch and she turned towards me. I loosened my pants and slid off my outer shorts and under shorts. My stiff cock sprang free and Mary stroked it and looked at it. I tried not to be distracted and continued to massage Mary’s anal sphincter and vagina. Finally after a few minutes I felt Mary take my cock into her mouth. I was thrilled because I took this as a signal that at some point Mary would allow me to lick and suck on her pussy. It was not long until I lost my focus as Mary blew me. I felt that wonderful tingle in my anus that signaled that I was about to unload. I told Mary I was about to cum and asked if she was ok, she just kept going and I spurted into her mouth, groaning as she slurped and swallowed. Mary was careful to suck me completely clean so that when I moved around between her legs I didn’t drip at all.

I resumed massaging Mary’s vagina with my finger still up her ass. I had never removed it and had felt her anal twitching as she focused on my cock in her mouth during the blow job. It was like a conversation. She spoke to me through her anal movements and I spoke to her through my throbbing cock as she sucked me. We were connected.

As I slowly massaged Mary with four fingers in her pussy, she groaned at how good it felt. I was up close to her and finally pushed the hood of her clitoris back revealing the little bud, and licked her. She reacted with a sudden jerk and exclamation, then settled down. I continued to explore her pussy lips with my tongue, gauging from Mary’s groans and reactions to which areas I should direct the most attention. Whenever I exposed her clitoris and licked it she thrust her hips and lost control. I didn’t stay on her clit for too long, because the intensity of it would cause her to pull away. I continued servicing her with my mouth for a good fifteen minutes, enjoying her moans, and groans and squirms. She was wet and my chin was slick with her juices. My left hand, middle finger up her ass was collecting pussy juice in the palm. I was enjoying her pleasure thoroughly.

After about fifteen minutes Mary’s moaning took on a new urgency. I felt her start to stiffen and was hopeful that things were leading to a release for her. She started to whimper and then that grew into a frantic cry. I knew that now was the time for me to start gently sucking her clitoris while I massaged her g-spot with three fingers of my right hand and her anal sphincter with the middle finger of my left hand. She seemed to fight the coming release and then it finally broke, and she cried out louder than ever and stiffened as if she was having a seizure. Then she started to shudder and I felt the waves of her orgasm wash over her. Her anus clenched my finger over and over. It was an intimate moment and I stayed with her until the long and intense orgasm was over.

Mary lay there seemingly exhausted. She had a dreamy happy look on her face. I sat up and felt the pussy juice dripping off my chin and wiped it with a corner of the sheet. I looked down at her moist, swollen pussy lips and the wet spot on the bed below. I realized that I was hard so I gently moved up and slipped my cock into Mary. I slowly withdrew my finger from her ass, and reached around behind her to cradle her ass cheeks and slid my finger back up her ass. She seemed to focus back on me when she felt my cock sliding into her. She sighed and I lay down on her, stroking her slowly. Finally we kissed and I realized it was our first kiss.

Mary and I fucked for about ten minutes. It was then my turn to cum quite hard and long. I squirted semen into her, grunting more times than I thought possible. My finger in her ass enabled me to feel my pulsing cock as I ejaculated. We were both satiated.

Mary thanked me for being thoughtful enough to patiently do what she needed so badly. I told her it was the best part of giving erotic massages.

We made plans to meet regularly.
Poster: Steve


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