Jogging

With my 39th birthday fast-approaching, I realized my body was not in the physical shape it once was. I had never been a fan of jogging, but seeing scores of men and women jogging at lunch time told me it was something I would have to try for own self. I work in a business complex near a large residential area that has a variety of parks and greenbelts. I asked a couple guys from my office where they jog and they gave me a few options in the area.

I bought myself a good pair of running shoes over the weekend and brought my running clothes to work. The first few days were a little warm and lack of fitness made the jogs brutal on my body. The two saving graces were the being outside in a beautiful area and the significant number of attractive women walking and jogging during the hour. Of course, some were women from the neighborhood and they were pushing children in strollers but even some of them were quite pleasant to look at as I struggled on my way.

A month into my daily jogging routine, I had settled into a good rhythm on two different paths. I began to see some of the same people on my runs. By the sixth week, there were four or five women that I specifically hoped to see while running. Of course, regulars would wave or smile as we passed by one another. One tall, long-legged brunette definitely caught my attention whenever I would see her. I remembered seeing her running by me every day for a week or so. She had long strides with her muscular legs. She would turn her head to smile and give me a quick wave. My eyes would stay on her firm ass as she pulled away from my sluggish pace.

For the past couple weeks, I seemed to see her almost everyday as she ran towards me in a couple different spots on my run. By now, I was feeling in much better shape and my stride was longer and much more confident. I would begin to smile as soon as I would see her running towards me. Her breasts, though not large, would bounce under the sports bra I'm sure she wore. My eyes would alternate from them to her beautiful face. Of course, I always made eye contact as she neared. Her smile would brighten her face and definitely put a spring in my step.

On Monday of my ninth week of jogging, my daily runs got a whole lot better. I was half way through my run and past the spot where I would usually see the brunette when my day brightened. I heard footsteps behind me so I turned my head when I saw the long-legged brunette sliding up beside me with a smile. "Mind if I run with you for a while?" she asked.

I took three or four strides before her words sunk into my brain. I turned my head slight, "Not at all - I'll try to keep pace." I grinned as I said it knowing she could leave me at any time. We settled into a good pace for the duration of my run. Seeing my car up ahead, I pointed "This is where I stop for today."

She slowed with me as I pulled up to my car. "I'm Mary," she said as we both caught our breath, me more than her.

"Pleasure to meet you. I'm Rob. I work in the business park." We chatted a couple more minutes and I told her I'd seen her running. She grinned and told me she had noticed me as well. Mary said she lived in the neighborhood and worked from home. She said she'd look for me in the future during the lunch hour.

We ended up running together most everyday for the next couple weeks. In my efforts to keep her pace, I found myself running harder than I had been without her. We would share a little chat as we ran and then she would always hang around while we cooled down from the run. Near the end of our third week of running together, she asked me if I'd like to just come to her place for lunch the next day. When I seem to hesitate, she offered that I might still get my cardio. That sealed the deal and she gave me her address.

#

Her house was only a five minute drive from my office and my afternoon was clear enough to allow for a two-hour lunch. I didn't tell Mary this in case it didn't go so well. She greeted me at the door wearing clothes not a whole lot different than when jogging. Except, I didn't think she was wearing her sports bra. Mary had her long, brown pulled back with a ring. She gave me a friendly hug and invited me inside her house.

It was funny - this wasn't a date and nothing was said explicitly, but it felt like we both knew why I was in her home. Mary offered me a glass of iced tea and I followed her into the kitchen. I admired her well-toned ass as she walked on low-heeled sandals. I took a long drink on the iced tea and sat the glass on the counter. I stepped forward and took her in my arms. When she didn't hesitate, I pulled her closer to me. I pressed my lips to hers and the kiss was friendly and passionate.

I could feel her pulling my dress shirt from my pants. Her hands quickly unbuttoned my shirt and I soon felt her strong hands on my chest. From holding her so close, it was immediately obvious that Mary works out in the gym, as well as all the running I knew she did. Her tongue pressed past my lips and wrestled with mine. She finally broke our embrace with a smile, "Well, I could offer you lunch ... or we can just move to the couch." I grabbed her hand and led her to the couch!

Before we hit the the cool leather couch, Mary had slipped my shirt off and I had helped pull her t-shirt off over her head. Her amazing 34C tits bounced in front of me. Her smile could light a dark room. I bent down and pressed my lips to her left nipple. My tongue flicked across it until I felt it grow hard and then I moved to the right. Her hands rubbed the back of my head as I tongued her nipples.

Eventually we tumbled onto the couch. My hands continued to roam on her supple breasts as we kissed. I could feel her hand caressing my crotch through my slacks. Mary slid off the couch and unbuckled my belt. I watched her as her fingers unzipped my fly. I stood up so she could lower my slacks and briefs. My cock was stiff and pressed against my body. Mary leaned into my body and looked up at me with a smile before lowering her head to my cock. I felt her soft, full lips surround the crown of my cock. The tip of her tongue flicked at my pee hole and I moaned out in delight.

Mary's right hand looped around the base of my cock and slid up and down the lower four inches from the base. Her mouth enveloped my crown and she began sucking on the skin. The sensation was electric. My hands began playing with her brown hair, clearly lost in the moment. As she lowered her mouth, I could feel her teeth raking the underside of my cock. Mary had my whole body on fire with the pleasures of her mouth on my cock.

She looked up at me and let my hard cock slide from her lips. I watched her stand up in front of me. She stepped back two steps and turned away from me. I watched as she wiggled out of her shorts. A second wiggle and her lace panties were on the floor as well. She slowly turned around with her hands in front of her. And then she moved her hands to her sides.

"Holy Shit, Mary!" My eyes looking at the long, semi-soft cock hanging between her thighs. My mind racing as I take I process what I'm seeing. I didn't have a clue, even as we started making out on the couch.

Mary stood naked four feet in front of me with her hands to her sides. Her long brown hair resting on her tanned shoulders. Her 34C round breasts and perky nipples beckoned to my touch. But I was totally unprepared for the penis that hung down between her slightly-parted thighs. Full, dark pubes covered the area above her penis. Mary had a smile on her face but it started to wane as she saw my surprise and hesitation.

I really was totally unprepared for this. My mind was racing as I thought of the days leading up to this. I had noticed her long legs and athletic ability - it's what had really attracted her to me, but I never thought she was anything but a genetic woman. I knew my once rock-hard cock was now hanging down like hers.

"Mary - I'm sorry. I don't know what to say - what to think!" She took a step towards me but I could feel myself rock backwards without even giving it a conscious thought. I too was standing nude in her living room. She had left her shorts on while we kissed and made out on the couch. Her hand was warm and strong as she stroked me hard while we kissed.

"Rob, it's OK. I really thought you knew. It just seemed like ..." but her voice trailed off as she watched my face. I'm sure it wasn't the first time this had happened but that didn't make things any better.

Mary then brought a smile to her beautiful face, "Don't say anything. Don't think anything Rob." Mary quickly covered the four feet between us and took my cock in her hand. I once again felt her warm, strong fingers wrap around my cock. My brain told me to flee but my heart was racing. Her left hand moved up and lightly caressed her breast as her eyes looked into mine. "Don't look down Rob. Just look into my eyes." I could feel my cock twitching from her touch.

Mary's fingers wrapped around my cock and began sliding over my skin. The silver ring below the knuckle of her thumb would rub over the tip of my cock and make me jump. I stared into her eyes and could feel my cock growing hard once again. As Mary felt this, she moved closer and pressed her lips to mine. I could see her eyes "smile" as my tongue slipped past her lips. Our kiss was once again urgent in nature. Her hand was sliding up and down the length of my six and half inches in a slow, steady manner.

My right hand began to caress her left breast. My touch was a bit tentative at first, but soon my thumb was rubbing over her soft nipple. Her left hand was now behind my head as our kiss grew in intensity. My cock was nearly hard from her steady stroking. Mary broke our kiss and looked into my eyes briefly before kissing me on the cheek. Her tongue flicked my neck and then left shoulder. Her hand never stopped stroking my cock. Her lips caressed my left nipple before kissing her way down my belly.

Finally she was on her knees in front of me. I looked down but could only see her face an inch or two from cock. Her tongue flicked past her lips and tasted my precum for the first time. My body jumped at the sensation. Lightly her lips covered the crown of my cock and her tongue teased my peehole, now wet with emotion. Her hand slowly stroked my cock from base to crown. I could feel Mary's lips open around my crown as her mouth slid over my shaft. Her warm mouth slid down my shaft.

Mary's hand moved to my hanging sac as her mouth began to fuck my cock. Deeper with each penetration, I could feel her lips on my skin. My sac was being pulled and caressed as her mouth devoured my hard cock. I soon found myself engulfed by her mouth and I knew I was about to cum. My hands ran through her hair as she bobbed on my cock. She gave my sac a squeeze and then released them. I thrust my cock into her warm mouth and cum exploded from deep within me. Mary hungrily took my cock deep in her mouth. The sensation caused me to shoot again and Mary didn't miss a drop of my warm cum. I could feel her sucking on my cock as her tongue licked me clean until finally she let me slide from her lips.

Mary looked up at me and then rose from her knees so we were once again eye-to-eye. This time I leaned into her and pressed my lips to hers. I could taste sparse remnants of myself on her lips. I pressed my tongue hard past her lips and pulled her body to mine. My hands wrapped around and caressed her firm ass cheeks and she embraced my lower back. I could feel her cock pressing against mine but it didn't matter at this moment as we kissed.

I saw a clock on the wall over her shoulder and realized I had been at her place for two hours! I separated from her and said I had to get back to the office. It was sincere but wasn't sure how it came out when I said it. I fumbled into my clothes while she mostly stood and watched. Before I left, I walked over and kissed her on the lips softly and thanked her for 'lunch'.

I thought about her ... and her cock ... for the next two hours while finishing up work for the weekend. I have never been with a man, or a woman with a cock before, but I couldn't stop thinking about her. I had enjoyed talking with her while we ran and found her athletic body so sexy. I knew I had a lot of thinking to do but also knew I wanted to see her again. I pulled out my phone and texted, "I want to see you again, Mary. Dinner Sunday night?"

Within the hour, I had my reply. "What time?"

#

I ordered take-out before leaving work and picked it up on the way home. Booting up my laptop, I opened a beer and dug into the dish of spicy chicken. I typed in "girls with penis" in the search window and started clicking on links. By the time I had finished my first beer, I'd already learned quite a bit about the terms 'transexuals' and 'shemales'. I was amazed to learn about this whole form of gender bending that I never knew existed until seven hours earlier when Mary lowered her panties.

I tossed my take-out container in the trash and opened a second beer. Taking my laptop to the couch, I sat down and explored further on the subject. I kept getting web hits for porn sites but I really wanted to read more about the topic before I gave in to just looking at pictures - after all, I had seen the real thing and had a date for Sunday night.

#

I arrived at her door with flowers and Mary seemed truly surprised. I kissed her lightly on the cheek as she invited me inside so she could put the flowers in water before we left. I had told her it would be casual, so she was wearing a blouse and mid-thigh skirt with heels. She looked quite sexy as she put the flowers in the vase. Dinner was at a favorite little place of mine near the beach. I knew the owner and he provided us just a little bit of privacy. Mary said she didn't usually drink very much, but we both ordered margarita's. I told Mary about the research I had done on Friday night. She seemed surprised when I could talk to her with a bit of an informed opinion. Mary was very open and gave me a brief synopsis of her life. When the waiter asked if we'd like a second drink during dinner, I was surprised when Mary nodded yes. "I thought you said you don't drink very much."

She leaned close to me, "I don't because it makes me horny." And then she smiled a sexy little smile that made me move around in my seat to readjust. After dinner, we went for a walk on the beach and talked some more about our lives but dancing around the subject of sex or the amazing blow job she had given me on Friday. Finally we were back to the car and I drove her home.

#

I walked her to the door and pulled her into my arms. Pressing my lips firmly to hers, I could feel her body melt into mine. My tongue tussled with hers as my hands circled her hips and firmly squeezed her ass cheeks. When we finally broke the kiss, Mary looked at me and smiled. "I hope that's a 'Can I come in kiss and not a good-night kiss'".

Grinning back at her, "If the lady insists ..." Mary slipped the key into the lock and pulled me inside behind her. She took me by the hand and led me straight to her bedroom. Just a low nightlight in the corner illuminated the room.

"Why don't you warm the sheets for us while I slip into something sexy for you, Rob." Mary slipped into the bathroom and closed the door behind her before flipping on the light. I looked around briefly before pulling back the covers or her large king-size bed. I pulled off my shirt and slipped out of my jeans and briefs. The sheets were cool and had the feel of being freshly laundered. I was guessing she would hope the night would end up this way. And when she opened the bathroom door, my guess was confirmed. Though the room was pretty dark, I could see Mary as she stood in the doorway backlit from the bathroom.

Mary was wearing a light-green baby doll nightie with a pair of matching panties and three-inch heels. She slowly walked to the side of bed and slowly turned around in a circle for me. The nightie was see-through with just a tie below her 34C breasts. The panties hid her penis but when she turned around I could clearly see her sexy ass that I had lusted for while jogging all this time. I was smiling widely as I watched her on display for me and I could feel my penis coming to life under the sheets. "Do you like what you see?"

I pulled back the covers as my way of response. Mary slipped off the heels and slid onto the sheets beside me. I slipped my hand under the sheer baby doll and pulled her close to me. Our lips met for a long, slow and passionate kiss. Her left hand slid over my belly and moved between my thighs. I moaned lightly into her mouth when her fingers touched my flesh. I untied her nightie and pressed my mouth to her left breast. I hungrily sucked and kissed her firm skin as my tongue flicked her nipple. My mouth moved from breast to her lips and back to her breast as her hand slowly caressed my six and a half inch erection.

"I want to fuck you, Mary." She smiled and kissed me on the lips and then rolled away from me. I could hear the nightstand drawer opening as she reached for lubricant. Her hands returned to my erection with a warm lotion she lovingly smeared on my skin. Mary moved to her elbows and knees as I pulled back the covers of the bed. She reached around and pulled down her panties below her cheeks. As I reflected back later, she was trying to keep her penis hidden from me so I wouldn't lose focus, or my erection. My hands caressed her firm ass cheeks as I moved in behind her. Mary's head was turned so she could look back at me as I pressed my cock to her asshole.

"Don't be shy, Rob. I'm a big girl and I know you want to be inside of me!" I moved on top of her as the crown of my cock slid inside of her. I could feel her opening up to take me as i pushed deeper. Three or four short thrusts later and my cock was buried inside her sexy asshole. "Mmmm ... you feel s-o-o-o good inside me, Rob." My body was now draped over Mary's with my arms on either side of her. I thrust in and out with my hips. As my tempo increased, I could hear the sound of my hips meeting her cheeks. Her asshole was so tight around my cock as I fucked her. Mary stretched her neck around and we kissed with my cock buried inside her. I could feel her grinding back against me every time I buried my cock. She knew I was close, "Cum inside me, baby. Cum inside me!"

I thrust quickly a few times and then felt my cum shooting from my cock. I thrust again and could feel her hole tightening around me. I was panting from the exertion and from the sensation. We rolled onto our left sides with my cock still firmly buried in Mary's asshole. "That was amazing! You are amazing!" I kissed her earlobe and nuzzled her neck.

"You feel so good inside me, Rob." We made small talk as I stroked her breasts while snugging my body tight against hers. I told her this was only the second time I'd fucked a girl in the ass and the previous time had been in college. We snuggled and dozed until a little after midnight. She was bummed when I told her I had to leave, but I had an early meeting for work in the morning and she understood.

She was still under the covers when I bent down to kiss her good-night. "So we on for a run at lunch?" she asked as I walked through the bedroom doorway.

"I'll be there."

#

Friday afternoon was our third run since fucking on Sunday night but we had not been able to get together for a repeat, or even a date. Life just got in the way for both of us. We neared the intersection by her house during our run. She looked over at me and asked, "Quickie?" We were both covered in sweat as we were three-quarters through our run. I didn't have a lot of time this afternoon but turned at her corner. Mary unlocked her door and we practically tumbled inside the house. In moments, I was pulling off her t-shirt and bra. Mary was pulling my shirt over my head in between kisses.