Being Bobs

By Al Blank

Published on Nov 7, 2013

Transgender

Let me preface this by telling you I'm a married middle aged man. Considered attractive by most women and in my younger days quite a few older men as my blond hair was long and I then it was the style to wear tight fitting jeans that really showed off one's ass. I was also very slight in stature. I've kept my boyish charm. I'm about 160lbs, and stand about 5'9", blond hair, blue eyes - your typical aged surfer look.

I am self employed and work from home. It's an ideal situation as I work in the creative field and love the downtime that is necessary to recharge my batteries. That downtime is usually spent doing the housework and cooking meals, looking after the yard and all the lovely jobs that come along with being a male house-frau.

Last week I was at the grocery store. I turned down an aisle and saw with pleasure it was empty. No shopping carts with screaming kids to manouver past - just one guy about my age or maybe a few years older than me with a basket. He was a large guy - a little intimidating in size. It was one of those things where eyes met and locked. He looked up at me and I found his gaze to be quite intense, but friendly due to the smirk on his face. I smiled back, but I dropped my eyes as I approached him. When I looked up again I saw he was looking at the shelves again.

"Damn", I thought. He's standing right in front of the coffee I needed. I stopped at another shelf to examine some product, but really to give this guy some time to select his choice and move on. I saw out of the corner of my eye that he had his eyes on my legs or ass and the stare was unabashed as he thought I didn't see. He had discovered what my wife calls a terrific asset and wishes she had a bottom like mine. I was wearing knee length shorts that really defined my round butt. Once I figured out his motive I felt very naked under his gaze. I found myself to be somewhat flattered. It's been a long time since I considered flirting with a man or had been flirted with. I'm not the cute twink that I once was. Well, he took his time and I was forced to approach him and say "excuse me" as I reached for my favourite brand. As it happened he reached for the same bag of coffee as I did and our hands touched. He smiled and laughed jokingly that he had finally made his decision and we had things in common. I smiled back at him and agreed with him. Then I moved on thinking about my grocery list.

As I rounded the next aisle, guess who was there again? It was one of those situations that he was running the same route through the grocery store axcept backwards to me meaning that every aisle we'd bump into each other. By the third meeting we were talking like old friends. I guess he found the humour in it as well. I picked the shortest line at the checkout and as I was waiting for my turn guess who siddles up behind me - but my friend from the aisles!

We chatted a bit about how this was the best time to shop as the stores weren't crowded and laughed at our tendency to bump into each other. My new friend said he didn't mind one bit. Now even for a miopic guy like me that hit registerred loud and clear. I must say I found it rather arousing. My heart started beating faster and my mouth went dry. My turn came and I got checked out now by the clerk...as well as my new friend. I was bagged and ready to go. Half of me wanted to stay and chat, but the other half calmed me down and told me not to make a fool of myself. I smiled a goodbye at my new friend and thanked the clerk. As I walked out I instinctively knew he was going to check out my exit. I don't know why, but I actually wiggled my ass a bit to show off - hoping I'd give him something to put in his spank bank.

Loading my purchase into the car I see my friend walking towards me. I looked up and gave him a big smile. He did likewise. His was the truck parked next to my car. Since I had backed in and he didn't our doors were on the same side. This put him right in front of me. Something about him made me want to play up my feminine side. He was quite a bit taller than me - I'd put him at about 6'4". And he outweighed my 160lbs by about another 100 lbs. I should have felt threatened, but due to his gentle nature I just felt oddly girlish next to him. He extended his hand with a bright smile and suggested we might as well exchange names. Bob had a warm hand that wrapped about mine like a leathery blanket. It was huge, calloused and obviously a working hand whereas mine was small, soft and at his mercy in his. Instead of getting that bone cruching macho grip I was expecting, he just held my hand gently and for a little while longer than what was necessary.

Bob suggested I pop over for a coffee at his place. Since I had nowhere to be, and the groceries I had bought didn't need refridgeration - but mostly because I was intrigued where this was going and agreed. I tried to be cool, but inside I was jello. I'm sure he saw my knees shaking with nervousness.

I should explain that as libra I have two different sides. This is the curse of the libra. We want to see both sides of an equation before we make up out minds.One side of me has been well exercised. As a husband and apparently a bit of an alpha male, I'm the top. I direct play. My wife loves my gentle , but forceful ways. But yet, I have always wondered what it was like to be the feminine part of the equation. To be persued and wanted - even lusted after. Now the difficult part - I don't find men attractive at all. But Bob's easy going manner seemed to calm me down. I actually found myself fantasizing scenarios with Bob. He seemed to fit the bill in that he was certainly masculine enough to make me feel feminine. And I liked that. And the knowledge that he found me attractive made me hot for him.

Bob lived two blocks away from the store. By the time I pulled up in front of his house, he was out of his truck and waiting for me by the path to his back yard. I hopped out and followed him to his kitchen door. We walked in and he placed his bags on the counter and put the kettle on making small talk. He asked me to have a seat on a stool while he put away his groceries. At one point he had to reach over me to place a box on a shelf. Feeling brave, I didn't move aside for him. This caused him to place his hand on my leg for his extened reach. His touch, just like his handshake felt electric. I realized I must have looked like a deer in the headlights. He smiled a sexy smile at me which told me he knew what I was thinking.

Bob placed a cup of coffee in front of me first and then served himself. He then brought out a tin from a cabinet and pulled out a bag of weed. With an eyebrow raised at me in inquisition he rolled up number for us to smoke. I smiled back and said "Sure"! The perfect ice breaker!

We moved out onto his secluded deck and enjoyed some herb and coffee. Bob sat right next to me on a 2 seater couch on his deck. I looked out into his back yard and saw it to be surrounded with bushes and trees witha nice dipping pool that dominated the space. We were both wearing shorts and the heat from his leg transferring onto mine was too much for me to handle. And it showed in my lap as my excitement grew. Bob chuckled at my predicament. He didn't jump on me to my amazement. He took it slow. In fact as time went by his slow hand was actually seducing me.

He went on to explain his situation how he had come out of a divorce several years ago and met a married woman on craigslist he sees once in a awhile. The sex is freaky good but that's it. He told me that it would take some time for him to trust women again. Bob also told me he liked his solitude too. And men, although many were into casual sex, Bob said he liked the natural feel of bareback so that option was out. He was so causal and honest about it I found myself trusting Bob as an open minded, liberal kind of guy. "It's way too dangerous out there for casual bareback play." Bob summed up. I asked him what he does to find relief and without blinking he told me he just masturbates a lot. He said he liked all kinds of porn, even gay stuff!

Bob went in and got us cup after cup of coffee. The conversation was great. The sexual electricity was driving me crazy. Finally I had to excuse myself to go pee. I got the feeling Bob was trying to delay my visit to the washroom. But since I was enjoying his company I repressed my urge to pee for a bit. This produced some squirming on my side which Bob laughed at and teased me about. But dammit...he kept on engaging me in conversation I couldn't get away. As time went by I had acquired a 5 star pee hard on going on and I could feel my underwear getting squishy from all the drooling my cock was doing.

I finally excused myself saying I just had to pee and would be right back. When I stood up, Bob pulled me down again so I was sitting on his lap. He took my weight like I was a feather and wrapped his huge arms about me. I felt like a fool for giggling, but that just seemed to goad Bob on. I continued to pretend to trapped, but for all intent and purpose I was. Bob's arm was almost twice as thick as mine and it felt like warmed iron around me. When I sat down in his lap I could feel something thick and hard under my bum. While I wasn't ready for this and the realization that another man was hard for me stunned me and made me gasp. Bob grabbed the back of my head and brought my face close to his for a kiss. "Mmmm, your "pussy feels so good on my cock" Bob moaned. I thought "what the hell" and settled into his wants. He gently gave me butterfly kisses to open me up. I responded so he licked my lip. I smiled and opened my mouth. It was then he captured me in a long, open mouth kiss. I kissed him back and felt his crotch involuntarily thrust at me. I squirmed more, half because I felt so hot and also because I was about to wet myself.

Bob placed his hand on my tummy and rubbed it. I moaned and squirmed as by poor bladder was terribly full. "You're going to make me wet myself!" I hissed at Bob. I tried to remove his hand. It didn't want to move! He whispered in my ear that it was okay to let loose right then and there. Bob told me he wanted my liquid warmth all over his lap and if I really wanted to make him happy to do just that. He also told me my clothes could go in the washer afterwards. So l leaned against Bob and snuggled while he kissed me and rubbed my tummy. He leaned back against the couch and he coaxed me to wet myself - to show him how much I wanted him by sharing myself with him this way. Stoned out of my head and so turned on I tried to squirt as Bob rubbed my tummy. His hand strayed to my cock and thighs an lot and everytime he touched those buttons I'd tense up so it was more difficult than I first thought. Plus I'd been holding it for easlily an hour and a half and had drank four cups of coffee so I knew I would entirely soak Bob if I really let go. Eventually Bob straightened me up in his lap and because of the sudden movement I felt a squirt let loose. Bob saw my look of shocked shame and was spurred on even more. I looked into his wanting face and saw how much he really wanted me to wet, so I relaxed and whisperred to him "Here it comes". I concentrated on peeing for Bob. It was easy to illuminate that tingling in my groin and down my ridgid cock. It It came with such a rush we could hear it. Bob starting dry humping my ass with his engorged cock. Then I saw it! And so did Bob...my wetness started in my lap...shown off dramatically by my khaki shorts. Soon the puddle soaked between my thighs and I knew Bob was being soaked. To confirm that thought, Bob just sighed and squirmed against my hot, soaking ass. In 2 minutes we were both drenched.

Bob looked at me and smiled a lecherous grin "You dirty little girl - seems like you're all wet for me!"His breathing was a little ragged. Bob rubbed his large hands on my thighs and crotch. I almost came for him right there! I had soaked myself and Bob in warm pee. and I imagine the indoor/outdoor cushions on the couch would need some serious hosing as there was pee dripping off of it underneath Bob's thighs. It was splashing onto the deck. I looked at Bob. His head was tilted backwards, his eyes were closed and he was smiling. All the time he was grinding between my soaking wet cheeks with his eager cock. I actually felt liberated that he enjoyed it so much. Somehow pleasing Bob seemed right.

Bob tilted his head back to me as I squirmed in his lap and asked me if I'd like to go to the bedroom with him. I just nodded and smiled - inwardly I smiled to myself that I had his attention. He took my hand and led me into his kitchen onto a mat. He pulled me in next to him. t was a small mat, but I got the idea to keep the floor dry. Bob reached in and undid my pants, zipper and hooked his thumbs onto the beltline of my shorts. Slowly he pulled down my pants making me entirely vulnerable to him. My shirt was useless in covering my hard on and it only covered part of my bum. He held me at arms length and turned me around, surveying his soon to be conquest and let out a low wolf whistle in appreciation. Bob then asked me to help him take his shorts off. I did likewise, but noted the resistence when I hooked his cock. I reached into his pants and unhooked him from his underwear. When I felt his cock for the first time with my hands I was struck. I'd guess about 8 inches cut with a beautiful spongy, pink head. His cock tapered into a thick, strong root. He was groomed too. I had to have more of this! It was hot and the head was covered in slippery precum. Oh boy..but I had his attention! It was also clammy from all the peeing I did. Bob reached into the counter and grabbed a tea towel. He the dried his feet and stepped off the mat to dry his legs and then my feet and legs. He put our clothes into the washer. All this time I stared at his huge cock bobbing in front of me which easily drwarfed mine. I inwardly made a check mark about large men being proportionate. My cock, although at the moment, ridiculously eager looking resembled boy's equipment in comparison. I shave my cock and balls and trim the heavy stuff back making me look - again by default - so feminine. My legs looked small and delicate next to him. As hard as I ever was before, my equipment compared weakly next to his. In fact my entire body was equally diminutive to his.

Bob looked at me and chuckled as took my hand This snapped me out of my staring and led me down the hall to his room. Butterflies were zinging in my tummy! His bedroom was sparce and masculine. Lived in, but clean. A huge and well made bed dominated the room. Off his room was a very comfortable ensuite washroom. It was here he led me. His shower was more of an area tiled off with large slabs of slate with a drain in the floor than than your standard shower. He stepped in and turned on the water. Bob held a hand out to me and I placed mine in his and I stepped into the spray. We both stood in the water as he held me closely. My arms instinctively held his back and the back of his head. He gazed at my mouth for a moment and then kissed me. Meanwhile as I was sucking his tongue, I felt him press hard against my tummy. I gasped a bit and he smiled a smile that I felt through his kiss. I pretty well melted into his arms and tilted my head back to accept his mouth on mine. Bob craddle my back with one hand and the other was tucked underneath my bum, pulling me closer to him. I was standing tippy toe now and Bob held my weight in one hand like I gravity didn't exist. After we teased ourselves a bit Bob lathered up a facecloth and gently washed me all over. He seemed to spent lots of time cleaning my but all the while telling me how pretty it is! His slippery fingers squeezed the globes of flesh and I'd feel one of his fingers stray onto my rosebud which made me moan. Teasing my most personal of spots... I felt myself wanting to open up to him. It was all too much for me! I felt myself starting to cum. "Way too soon!", I thought. So I squirmed out of his arms to return the favour to him, lathering his arms and chest. Bob asked me to wash all the pee off of him so I got on my knees with my face cloth and soap. Bob's half erect cock jutted out so beautifully. His big balls hung low in the warm water. I quickly washed his legs and made sure to bump my head a few times on it. I needed to have him in my mouth! What a strange thought for a mostly hetro guy to think. But it seemed so right, so natural. I just had to taste him! I nuzzled Bob's balls with my face thinking how much delicious cum was in there for me. I kissed Bob's girth from his thick base to his tapered head. This was a cock that took charge and was built to prenetrate! I felt compelled to worship it! My mouth opened all by itself and I made very effort to engulf it. I tried to open my throat, to accept his need but only succeeded in making an embarassing "gak" noise. Bob's moans and a gentle hand on the back of my head to me he appreciated my work. For all my efforts I was rewarded with Bob's cock engourging to full size! It looked so mean and rude! After about 10 minutes of this, Bob figured we were clean enough and we stepped out where he patted me dry and then himself.

He joined me in the bedroom where he kissed me again. As we kissed his hands all over me exploring every inch of my skin. He backed me up until my legs pressed against the bed. The bed must have had two thick mattresses on a pedestal...I tried t o fall back onto it with Bob on top of me, but the mattress was above my bumline. Bob placed his hand under my butt and simply lifted and gently set me down on top of the mattress. He stood right in from of me and insinuated himself between my thighs. He laid me back and kissed me again while reaching over my head for something. I heard a pump action bottle go off about 6 times. Bob stood up and I watched him from between my splaid legs. "He was all man.", I thought to myself. And he was hot for me! I felt his need for me and that drives me wild! I also felt a slippery, thick finger seek out my rosebud. Bob chuckled and said "Let's get your pussy wet for me, baby". Bob always seemed to refer to my ass as a pussy. I liked it! It re-inforced the idea of him obviously being the man here. Meanwhile his finger pressed slippery stuff into it. His pressure was gentle, but insistent as he went around my "pussy" I relaxed a bit and it breached my hole. I gasped and squirmed on his finger. Bob leaned over me again and kissed my neck as I felt the erotic, tickley feeling of his finger sliding slowly into me. He wiggled it and I moaned and squirmed involuntarily. He but he told me that peeing is a huge button for him and if we could skip the foreplay as he really needed to be in me right now. I smiled back at his obvious eagerness and spread my legs a little further for him. While he did this he moaned and told me he was going to own this pussy. I writhed on his finger and kissed him back as he held me in place. Bob's finger slowly slid out. My pussy felt empty and my hips thrust up to meet something...anything.

I opened my eyes and saw Bob rubbing lube on himself. Still on my back, Bob pulled my knees towards the edge of the bed in one gentle movement. He then pressed his cum-filled balls against my ass and ground himself into me as if the contents could be transferred into me that way.

I sighed with lust. My fantasies were coming true! Bob rubbed the head of his cock up and down my crack pushing slightly at my pussy until he felt the flesh accept him. I felt totally at his mercy and completely violated. I loved it! Then he settled on the hole and wiggled his meat back and forth as I got used to the girth. He was so gentle it didn't hurt at all when the head popped in entirely. Bob just stayed still for a bit to let me get used to him. It felt like a hot, but friendly intruder and I knew I was going to give Bob my most intimate gift - me! Bob teased me with it. He'd slip the head in me and take it out. Each time he invaded me, he'd push just a bit farther into me. With the wiggling and popping it in and letting it slip out again I felt like I was going to scream! I just needed to be filled by him! I tried to thrust back - to take him all inside of me, but Bob smiled at me wickedly and moved away...he asked me to beg for it. Oh I begged! Bob let it slip in a inch at a time slowly, but without retreat. I felt him invading my most inner sanctum. His cock was large enough to make me gasp as I felt my insides making room for his unrelenting occupation. Bob must have been worried about hurting me. He pulled out again and slowly, ever so slowly pushed back in again. I was totally stretched out and loving it! When Bob finally bottomed out I felt his swaying balls rub up against the top of my ass. I was a mixture of glowing and on fire with lust. My breath was all of a sudden hard to grab. Bob sensed the effect he was having on me and ground his hips into my upturned pussy, my legs held firmly back and splayed so he could gain better access to me. I was totally pinned to the bed and couldn't move other than to thrust back weakly at Bob's manly thrusts into me. It seemed no matter how Bob moved, with his girth he seemed to hit my prostate no matter what angle he pushed at. Bob grabbed my hands and placed them over my head. I noticed his arms were the same size of my legs. All I knew was at that moment, Bob owned all of me. He then leaned down over my quivering form and kissed me passionaltely on the mouth. I wrapped my legs about his back. I so wanted him there, inside of me, having his way and bringing him pleasure with the warmth of my inner recesses. Bob started to pound into me. I was a little nervous as he was totally lost in lust...I was starting to receive a little more than I could keep up with! I couldn't keep my poor pussy co-ordinated with his invasive cock so I just relaxed and let him fill me. Instead of participating now, I was just a fuck hole for Bob. He seemed to respond to me loosening my pussy-grip on his cock as I felt him swell and pulse in me. I looked up at Bob and he made all kinds of grunting noises as he came hard into me. As he did, he pushed hard into me so his seed would deposit as deeply as possible. I felt like I was being bred by him! He came for a minute or two! His spasming cock just kept pumping cum into me. I felt it fill me up and felt my ass even getting wet! Knowing that I had pleased Bob and my duty was done, it was somhow okay for me to come and that I did with ropes of juice squirting from my much ignored cock. Bob looked down on me and smiled as he saw me cumming. I was a panting mess. My hair was sweaty and my pussy felt hot and full. Bob leaned over and kissed me a few times telling me that was wonderful and thanking me. I merely snuggled into his arms and hugged back with legs on his back and hands on his ass as he finished draining into me. Our torsos covered in my spray...

When Bob finally pulled out of me, I felt empty.

My pussy felt stretched and gaping. Bob noticed and seemed to glaze over at the sight. He laid on his back on the bed next to me and picked me up with his huge arms and placed my ass on his face. I was so shocked as I never expected this move! He held me there and I supported my weight with my knees splayed open over him. I felt his tongue lick my ass and a lot of slurping noises. Bob was cleaning me up! Bob's lips clamped on my poor, swollen rosebud and I felt his tongue snake up into me. I sighed with pleasure and Bob ate my pussy with obvious desire. What was nice is it seemed he respected my poor tortured backside. I helped him out by pushing out his semen so he could swallow it. Bob responded by scooping semen out of me with his tongue! In this position I could reach around for his cock and noticed it wasn't quite flaccid - but yet not hard. But even after two comes Bob was stirring again! It seemed he really liked this this little twist!

We washed with another shower. This time concentrating on getting cum off ourselves we chatted. Bob appologized for going bareback with me. He assured me he was squeaky clean. I returned the favour. Bob went further to say that he'd love to do this again. "Nothing would make me happier Bob!" I said with a huge smile. After our shower we had another joint and another cup of coffee. As I sat I noticed a bit of Bob's seed was leaking out of me still. It felt warm and wet. I had to clench my cheeks to keep from an embarassing wet spot. I reached for a couple of tissues to clean myself up and put in my underwear to protect my pants until I got home. I asked Bob how much he poured into me anyways?! He just smiled and told me he likes me a lot.

We made more small talk and it wasn't just filling up empty air...it was interesting. Somehow or another Bob directed the conversation back to us and what we just did. I couldn't help but blush and I think he found that endearing. Yet he plunged ahead and asked me all kinds of questions... sussing me out; He asked me if what we did really turned me on as much as it turned him on...Bob seemed squirmy, lke he had something to say, but didn't want to reveal too much. I told him to "blast away" with whatever was on his mind. He said he'd consider that for a while and get back to me.

Looking at the clock I saw that 3 hours had elapsed with my tryst with Bob. I had to get back to my real life. Bob grabbed my phone number and said he'd text me sometime. I smiled at him and he stood as I did to go. Bob grabbed me about the waist and pulled me into him, easily putting me so off balance I fell into him. His other hand rested on my ass. He tilted my head up and whispered "thank you for a wonderful time. I really want to do this again." The he leaned into me and kissed me gently, but masterfully. I left with another hard on.

More to cum....?

Next: Chapter 2


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