"Ah Brad. Glad you could make it. I hope you have not been miserable all day. Trust me when I say this whole thing does not have to be I pleasant. Would you like a beer?"
I can't really even answer so I nod my head and he leaves to I assume get a beer. When he returns, he is holding two bottles of beer, one of which he hands to me. "Now Brad tonight I have a little something planned for you." As we drink, he explains that my task for tonight is to have sex with Evelyn while he watches. She is already upstairs in the bedroom and waiting for me, so after we finish our beer, he leads me there.
The room is dim but not dark, and I can clearly see Evelyn laying on the bed naked. She is older but still in fairly good shape, without the fat or flab that so many older ladies acquire. Dr. Stevens, Carl, nudges me forward towards the bed so I walkover. As I get closer, I can see her fit form even better and am impressed with how she looks. Her breasts are small, so they are flat but don't sag like so many of the pictures I have seen. She is trimmed but not shaven and the peppered gray hair matches her head. As I get closer Carl tells me to undress, so I do. I can hear him chuckle as my already hard cock appears. As I get to the bed, I can see that Evelyn is staring at me, while just laid out on the bed.
"Kiss me" she says, so I walk over and place my lips on hers. I feel her hand pull my head tighter while her other hand grabs my cock. Her lips parts and I feel her tongue seeking mine. Her other hand is gently stroking me. I am already hard. Without releasing either head she pulls my face to her breasts and I pull a nipple into my mouth. I feel her breath catch as my hands touch her. One hand is on her other breast and the other is sliding along her stomach. Her skin is soft and warm to my touch, and her nipple tastes of soap and smells of strawberries.
"Lower" she whispers as she pushes my head down towards her stomach. I moved my lips and tongue along her stomach and towards the peppered down on her pubic mound. Kissing lower and lower I run my tongue through her dark curls, inhaling her warm scent. Already I can smell her and know she is getting aroused, even before my lips feel her dampness. As I move my face between her legs, I feel her shift and her warm mouth envelope my member.
I almost cum right then. The situation has me so aroused I can barely contain it. She slides her mouth along my shaft, and I can feel her tongue swirl and slide along me. At the same time, I am overwhelmed by her warm wetness. Her scent fills my nose and her wetness coats my tongue as I push further and slide it between her nether lips. Her clit is huge and stands like a tiny erection as I run my lips and tongue over it. As she spreads her legs, I push my face further between them, licking and sucking her. As she begins to shudder and tense, I push my tongue into her, rolling it across her moist lips. The shuddering lasts for a bit but as it stops, she pulls my face back to hers and kisses me deeply. I can smell me and her on her breath and feel her moisture on my face.
"Mount me from behind" she whispers to me before she breaks the kiss and moves to put her stomach on the bed while kneeling on the floor. I step behind her and feel her hand guide me into her. She is so wet I slide in easily. She feels amazing. Sliding all the way inside I hold her hips and pull her buttocks all the way towards me. In moments I am pounding into her, the wet slapping noise filling the room. "Shit, I'm cumming" I moan as I feel the need for release rising.
"Fill me" she moans as I feel her fingers begin to work her clit. The first shot erupts from me and I press into her holding myself deep. Can feel her vagina clench as she presses back against me and shudders herself. Our mutual orgasms mixing and flexing as we kneel locked together. Minutes pass like this as both of us struggle to breath and our minds drift off to the places that only post climax minds can go, but eventually I begin to shrink and without a sound drop from inside her.
I can feel the cum running down our legs, but we stay against each other. "Lovely" Carl's words startle me as I suddenly remember where I am. Looking over I see him wiping his now shrinking penis off with a towel. "So, was that so bad?" He asks as I stand up and take a towel from his other hand. "Evelyn needed a little attention, so I appreciate your efforts."
As I wipe off, I watch Evelyn roll over and open her legs to show herself to Carl, who smiles as I see my cum bubble out of her. Carl just stares with a stupid grin as Evelyn slides her finger through the cum, pushing some back inside and spreading the rest over her skin. It is a mesmerizing scene. It takes a moment for me to notice that Evelyn had started rubbing the moist mixture further underneath herself. But I notice when she rolls over once more on the bed spreads her small ass cheeks and exposes the small wet button hidden between. "Come on" she whispered as she holds her cheeks wide. I didn't need much encouragement before I was rubbing the head of my already rigid cock from her dripping crotch to her already wet and opening anus.
Pushing the head of my cock into her is a slow process. Each gentle push spreads her wider, which allowed more of me into her. Already she is moaning and grunting. After a few more pushes I slip inside her. As my full length pushes into her, she groans loudly and falls forward onto the bed. "Oh God yes" escapes her lips "fuck my ass you sweet sweet boy.
Already I am pumping into her. She is so tight and warm as I hump forward, it's amazing. I have never had anal sex before and realize now the unique tightness that her back foot provides. It is an all enveloping warm tightness that makes each thrust feel like heaven. Once again, I find my pace quickening as the need for release grows once more. This time is not the simple relief of my first time but rather the gentle build that results after the easy cum. This second session has always been for my partner, as I can go for long minutes without being overwhelmed by a desperate orgasm. Thrust after thrust pushes Evelyn into the bedding. Her hands clutch the sheets as I watch her eyes roll up and her mouth hang slack. Grunts, groans, and moans fill the room as I continue to pound her ass. It is amazing for both of us as she hit multiple orgasms and I begin to reach that second extended release.
"Oh! Oh!" I wail as I feel the wave of relief flood over me, mirrored by the small flow streaming into Evelyn. My legs tremble and my knees threaten to buckle as the last of the orgasm passes over me. As I began to once again notice the world around me, I feel the shuddering spasms of Evelyn as she is racked by waves of pleasure. I collapse across her back, resting my head on her back as I hold her hips to steady myself. After several minutes I pull my hips back, pulling my shrinking member free of her now gaping ass. I don't stand yet but instead just press my flaccid cock into the warm wet crease of her ass. There we stay just breathing until Carl tells me to get dressed and come by his office at 9 in the morning. Dressed and in a mild stupor I walk to my car and headed back to my apartment. It's only a little after 10 but it feels far later. After a quick shower I collapse into bed and am soon fast asleep.
