01/09/2025
I was on my way to give Mary her second sensual massage. I reflected back on that first time reviewing in my mind what she liked especially and how I could make it better for her. I remembered how she moaned softly when I slipped my lubricated finger up her ass. She loved every second my finger was in her ass, as I stroked and massaged her anal sphincter. I also remembered that she did not cum that first time, but she did react with exclamations of "oh that feels good" when I slipped three fingers into her vagina, while keeping the middle finger of my left hand up her ass. I pondered how to make it even better, and even get her to have a nice orgasm.
I remembered that during her last massage that Mary was clean and fresh. Her pussy became nice and moist as I massaged her and she smelled nice. I wondered if she'd let me use my mouth to help her cum this time.
Mary must have been looking for me, because as I pulled into her driveway she came out to meet me. She apologized and told me that her friend Rita was there. Rita was interested in a massage too, but wasn't sure so she wanted to see how it looked when I massaged her. She said she was sorry to spring this on me but it was a last minute thing. I told her it was ok, if she was ok with her friend watching. So we went inside and Mary introduced me to Rita. Mary was in her early sixties, a retired flight attendant with a fairly decent body. I found her attractive and enjoyed giving her erotic massages. Rita seemed to be about the same age. She was a little heavier and had dark hair. As we chatted, I considered that I'd probably be ok with being intimate with Rita if she wanted things to go that way.
After a little small talk, Mary wanted to get started. I think she was horny in anticipation of the massage. The last time was her first time so she was nervous at the start. Once I had her relaxed and fingers inside of her, she clearly welcomed the pleasuring even though she didn't cum. I must admit I was looking forward to massaging Mary even more since another woman would now be present, watching.
We all went to the guest room where the massage was to take place. Rita sat in a chair in the corner and Mary excused herself to go to the bathroom. I arranged a sheet on the single bed in the middle of the room. Rita and I talked politely and she seemed genuinely interested in getting massaged. She said she was a bit embarrassed to watch us. I quickly told her it was ok, and that it would probably enhance the experience for all of us. Mary came out of the bathroom with a robe on. She slipped it off and climbed onto the bed and laid down. She had on bra and panties and I didn't suggest she remove them like the last time. I figured it had something to do with her not wanting Rita to think she was too anxious. Mary was laying on her back like the last time. I always give my clients a choice but prefer to begin face up. That way the second half of the massage phase is with her being face down making it easier to transition to the anal sphincter massage. I've found it's less embarrassing and therefore relaxing for the client to experience my finger slipping up into their anus without eye contact. I also enjoy the sight of my finger sliding in slowly into a new clients ass. Many times I am treated to an exclamation of pleasure, or a moan.
I began massaging Mary at her head. Temples and a gentle facial massage. As usual I took my time. Moving down to Mary's shoulders. Slipping off her bra straps. Massaging and eventually removing her bra. She was now laying face up with only panties on. I glanced over at Rita. She looked comfortable and smiled. I completed the face up portion of the massage by massaging Mary's feet. I had worked my way down her body, massaging stomach, thighs, calves, etc. Mary was relaxed and breathing deeply.
I had Mary turn over and lay face down. I then removed her panties. I always enjoy this part, gazing down on a completely naked women. Enjoying the lines of her body, the fullness of her buttocks. Her aroma was musky. She must have been getting moist in anticipation. I slowly put on a blue exam glove on my left hand. It was quiet in the room. An air of anticipation was heavy. I could hear Mary breathing now, she was getting excited because she knew what was coming. I lubed up my middle finger and asked Mary if she was ready for a little cold on her anus. She just nodded her head. I slowly and gently spread her ass cheeks with thumb and forefinger of my right hand. I heard Mary catch her breath as the cooler air of the room washed across her inner ass cheeks and anus. As I gently lubed her anus, Mary moaned ever so slightly. I don't think she could help herself. I glanced up at Rita and she was mesmerized watching her friend in this ever so intimate situation.
I told Mary to take a deep breath and hold it until she felt my finger slide up her ass. She was then to breath normally. As Mary took the deep breath, I pressed gently and felt my finger glide into her anal passage. When Mary exhaled it was with a deep "Ahhhhhhhhh". I kept my finger as deeply as possible in her ass. I would re-spread her cheeks a couple of times to make sure I was in up to my last knuckle. I then kept it in place as I slowly massaged her back and upper buttocks with my right hand. I knew that her private areas were becoming increasingly sensitive with blood flow and that Mary was embracing a feeling of surrender, knowing that she was completely naked and safe on the bed. She knew that I could see every intimate detail of every part of her body, nothing hidden.
I heard Rita murmur and looked up. She was staring at me with a look of incredible need. Then she caught herself and smiled. I smiled back and turned my attention back to Mary. Mary was squirming slightly. I whispered to her that she could turn over if she liked and that we'd do it slowly so I could keep my finger up her ass.
With Mary on her back I continued to lightly rub her lower abdomen. With my left hand I slowly and gently slid my middle finger in and out of her anus, sometimes withdrawing so that my fingertip was just touching her. Then I would slowly and sensually slide my finger back into her ass. Mary lay there apparently in ecstasy. She was grunting softly. When I withdraw my finger from her ass, I would feel her anus pucker as she got ready for me to push it back in.
Rita asked Mary if she felt good. Mary just moaned a little and said it was heavenly. Then Rita said something that made Mary and I both get quiet.
"If you blow him I want to watch."
Mary and I were both silent. Finally I said awkwardly,
"I never expect or need anything during a massage."
I was keenly aware that my balls felt pretty achy and full, but wanted to make Mary feel at ease.
The massage continued as I began to introduce a bare finger from my other hand into Mary's vagina. She moaned some more and spread her legs wider.
Finally I had three fingers in Mary's vagina, I was pressing on her g-spot as I massaged her anal sphincter with my other hand. Mary was really relaxed and seemed to be on a path that would lead to orgasm. Mary was reacting to the physical sensations in a primal way. I noticed she had started to play with her nipples since both of my hands were inside her. I leaned down and took a chance, lightly licking her clitoris.
Mary gasped, taken to level she was not expecting. I settled in licking and sucking on her upper lips. I felt her moisture increase as she got ready to cum. Finally I felt Mary's anus clench my finger tightly as her orgasm approached. I felt the exact instant she began to cum. She cried out and started pumping her hips while her anal contractions released the built up energy in her body. As her anus contracted on my finger, I moved it around to enhance the intensity. Finally she exploded. She cried out and I felt the gush of her juices as she came.
Rita sat quietly. She seemed shocked at Mary's intense orgasm although she seemed to be pleasantly surprised. I was happy that I was able to make Mary cum and was smiling. Mary lay there languishing, drowsily in the afterglow of her orgasm. She pulled me down to whisper in my ear,
"Thank you so much. Please, I need you to fuck me."
After saying that, Mary got up on her elbows and knees and faced away from me on the bed. I had a perfect view of her behind as she faced Rita. I wondered if I could keep an erection with Rita watching, but quickly realized that it was making me even harder. I dropped my pants and I groaned in relief as my erect cock sprang free and I felt the relative cool air on it. I moved up to Mary's ass and slowly entered her with a groan. She was ready, very wet and warm. I slid into her easily all the way. Mary sighed and moaned too as she felt the fullness of my cock sliding all the way into her.
Mary and Rita were looking at each other as I slowly stroked my six and one half inch cock in and out of Mary. Usually when fucking for the first time I wasn't able to last too long, but this time I could look up and study Rita's face as she watched Mary's facial expressions as I fucked her. It helped to distract me so I was able to last a bit longer. All in all, it was about five minutes - 300 seconds, experiencing each intense second. Finally I could stand it no longer and as I spread Mary's ass cheeks so that I could thrust as deeply into her as possible, I ejaculated deep inside her with a series of grunts. Mary cried out as I injected my cum deep inside her.
Rita exclaimed,
"Oh My! That was so nice to watch!"
I was somewhat embarrassed to pull away from Mary because it gave Rita a clear view of my now deflated penis, slimy with the juices of our fucking. Once I did though, it was ok. I picked up my pants and excused myself to go to the bathroom to clean up. I was clearly aware that Rita and Mary were watching me walk out of the room, naked from the waist down but still wearing socks. I purposely dropped my undershorts in the doorway so that I had to bend over to pick them up. I heard a reaction from the ladies when I did that.
In the bathroom I saw Mary had laid out a towel and washcloth. I decided to shower quickly since I wasn't exactly sure what was going to happen next. As I gently soaped and washed my balls, I wondered if I would be fucking Rita later. I felt a slight stirring of my cock at the thought.
After the shower I found Mary and Rita having coffee in the kitchen. I thanked Mary for the towel and washcloth and the opportunity to get freshened up. Mary offered me coffee, remarking with a smile that I could probably use a break. As we sat and talked I asked Rita what she thought of what she hand witnessed.
She replied,
"Oh, it was very erotic like Mary told me. I hope you have time to give me a massage too."
I looked at Mary questioningly and she just nodded that it was alright. I said that I had time, so Rita got up and went to the bathroom to prepare for her massage. When she was away I asked Mary if she was really ok with whatever Rita and I ended up doing during the massage. Mary looked at me and said,
"You've cum once this morning, I hope you're good for more. I want to give you a blow job later after Rita leaves, so I hope you'll save some for me."
I replied that given enough of a break between times that I've been known to go four times in a row in fairly short order. So it should work out. Mary looked pleased.
After about fifteen minutes Rita came out of the bathroom. She had showered and had a single towel wrapped around herself. We got up and went to the bedroom. Mary stayed behind, telling us that she would look in on us from time to time.
I think Rita was a little horny and excited after watching Mary and I and knowing what was possible during her massage. She let the towel drop and got up on the bed. Her body was fuller than Mary's. She had large breasts and wide hips. I noticed that her pubic hair was nicely trimmed. I felt my cock swell a little in my pants.
I began the massage as usual. When I first touched Rita, she sighed deeply. I followed my standard routine, touching Rita everywhere, massaging her individual fingers and toes. She sighed deeply when I massaged her feet.
Finally I got to the point where I put on an exam glove, lubed up Rita's anus and gently slid my finger up her ass. She moaned,
"Oh that feels so good."
Rita's breathing became increasingly heavy as I slowly stroked my finger in and out of her ass. When I introduced a finger into her pussy she moaned some more. I decided that I was going to start eating her pussy and while it was a bit presumptuous, I took a moment to take off my pants so I was naked from the waist down. My cock was hard and throbbing. Soon after I started licking Rita, I felt her lick the head of my penis.
As things progressed we ended up in a sixty nine position. We started with me on top, but Rita requested a switch so I ended up on the bottom. It was at that point that Mary looked into the room. She had a good view of my spread thighs, balls hanging down and Rita with her mouth full of my cock.
Rita started pulling away as her orgasm approached. She would let my cock slip out of her mouth as she lost control and pumped her hips, pushing her pussy deeper on my mouth.
When she came I felt a gush of fluid washing down over my face. It was smooth, velvety fluid with a clean smell.
Rita had evidently forgotten about me. She got up and exclaimed how great that was. She went back into the bathroom as I stood there, still erect and aching. I needed to cum. I stood there for a little while while my erection deflated. When I was able to put my pants back on I did so and went out to join Mary in the kitchen. Rita came out at about the same time and said she had to run. She thanked me for a great massage and left.
Mary looked at me and asked me if everything was alright. I must have looked pained because my balls were aching from the incomplete blow job Rita had imposed upon me. I told her that Rita had kind of hung me out to dry.
Mary exclaimed in surprise that she had seem Rita blowing me. She was aghast that Rita had not finished me off.
Mary went into the bathroom and came out with a towel. She draped it on the kitchen table and told me to take my pants off and sit on the table. I found it exciting that she took charge like that.
I sat on the table, legs spread with my feet resting on arms of the chair. Mary came over with a wash cloth and gently wiped my scrotum and penis, which was rapidly becoming erect. Then she ducked under my leg, and sat in the chair. She pulled it up a little and told me,
"This is my regular place at the table. Now when I eat my meals, I can think about today and how I sucked on your cock and swallowed all your cum."
She knew what those words would do to me. I smiled and she slowly began licking my balls.She was moving slowly. She was going to savor the taste and smell of my genitals. I saw a bead of pre-cum appear at the tip of my now fully erect and throbbing cock. Mary saw it and promptly flicked it off with the tip of her tongue.
I moaned.
Mary skillfully licked, kissed and all too briefly sucked the head of my penis. Her actions were designed to keep me on the edge - crying out, grunting and moaning, without causing me to cum. At one point she pulled away, looked me in the eyes and said,
"I'm going to make this last, so relax. At the end, you can trust me. I'll let you finish deeply in my mouth if you want, and I'll swallow every drop of what you have to give."
I nodded shakily and moaned as she went back to work.
Mary kept her word. She slowly and sensually worshiped my cock with her mouth. Sometimes licking the shaft and sometimes suddenly taking me deep in her throat. I'd always moan involuntarily when she did that. She always stopped short of taking me over the edge. It settled into a symphony of my cries of delicious agony and her masterful domination. Mary was indeed in total control.
After what seemed like an eternity, Mary had me squirming and crying out without regard to how I sounded. I had no control. My balls were soaking wet from Mary's saliva and my prostate leakage. The towel I was sitting on had a large damp spot from all the fluids that had dripped from my scrotum.
Then Mary stopped. She looked me in the eyes and smiled sympathetically at the need she saw there. She said,
"I'm going to finish you now. I'm going to slip my finger up your ass and I'm going to take your penis into my throat. I want to feel every pulse of your prostate as you empty yourself into my mouth."
I uttered some incomprehensible moan.
As her finger slid up my ass, lubricated with saliva, she took my cock into her throat. She sucked and swallowed. I could feel her throat muscles caressing the head of my cock.
Then I came. It was stronger than I had ever remembered. I remember through a fog that I was making sounds that I didn't even recognize.
When the fog cleared, and I lay back on the table, feeling empty and supremely satisfied, I thought how I had just had an encounter with a real master. Mary knew how to service a man.
Mary kind of mothered me, getting a warm washcloth to clean me up and helped me with my pants. She was pampering me to the end.
As we said good bye that day, I gave her a hug and kiss. We agreed that we both wanted to continue this friendship.