‘The Beginning of a Relationship’ firstname.lastname@example.orgOver the course of the next month Jack and I became not only lovers but friends. He was a widower with grown c***dren and the (retired) CEO of a small family business. I found out that he was a very easy going and relaxed guy; he was interested in companionship and sex. The problem was that he’d met me as a ‘gal’ and loved that. However, this meant that I was always in the background like a mistress. As we went along, although it didn’t really bother me, he started to feel some guilt about it. I did understand how a ‘mistress’ felt though.He made up for these feeling of guilt by not only buying me nice things but trying to give me ‘special’ attention whenever possible…I didn’t mind that a bit and damned sure didn’t take anything for granted…I was always appreciative and tried very hard to show this.He was also appreciative of what I went through most of the time. Jack came to understand what I had to go through – endure – to make the transition to ‘Bobbi’ and that meant a lot to me. When we went out together (and I was femme) I didn’t want people to look at us as a joke. I wanted to look good enough to make him proud and to turn heads if I could – I was always careful as hell to ‘be’ 100% femme. Looks, actions, manners, everything. For me it was pride and wanting to make his life more enjoyable in any way I could. I have lips that are a little fuller, my chin isn’t strong or prominent and my ‘Adams apple’ is so small that it’s not noticeable at all. I’ve never had much facial hair.Our relationship, while semi-casual in nature, was a good healthy one. Over time we were also falling in love. I tried to not think about that because I was promiscuous by nature (a slut) and liked that. The problem was – for Jack – I was loving, attentive and totally submissive toward him…the ideal ‘girl’ without a pussy. He handled the male role very well; loving, caring, attentive and sometimes a little strict; pre-70’s style. I could (sometimes) be a brat and a tease. If I pushed the wrong buttons I was apt to find myself bare-bottomed, over his knee. He was doubly loving and caring after some of these ‘lessons’ as he called them.After a little while we began going out for dinner at least once a week. These weren’t anything but a normal night out; it could be any night from Sunday to Tuesday depending on his schedule. He started to call them ‘dinner and a fucking’. There was one place he liked a lot so we frequented it a lot. I started to like it too for a few nice reasons. It had been around a while and was well known however, it was past its prime. Still, it was clean and, not only had good food but the staff was very nice. Most of the waitresses were in the 40 to 50’s age group, nice pleasant gals. There’s a vibe you pick up with people…we went there with me in the male role a few times but, rolled the dice once (because of a semi-special occasion) and nothing changed. They even seemed a little warmer, friendlier and totally accepting of us both – mostly me.This was a fairly important ‘date’ and I wanted everything to be right. I didn’t want to embarrass Jack or get laughed at. I really wanted to get very close in a public setting – not just be a guy in a dress!It was one of the times that I really put my heart into it. I went as far as getting a cut and style (casual) a few days ahead of time. Every item of clothing was chosen well ahead of time, inspected, re-inspected and cared for; right down to the color and style of panties. I was going to wear a nice tasteful blouse with long sleeves and button cuffs that buttoned up the front, a very casual print A-Line skirt that caught me just above the knees, white lace bra, white garter belt with seamed stockings (which turned Jack on like hell) and white French-hi cut lace panties. The skirt was a very subdued print; I’d sprung for bahis firmaları a new pair of heels that complimented some of the colors in the skirt – the panties were new too.This was also one of the times I did a ‘dress-dressing’ to make sure the outfit worked together…it did.For this one I started very early, even calling Jack and asking him to NOT dare come until he was ready to pick me up! He’d caught me in my lingerie once and we never made it to dinner…after I’d spent well over an hour on fucking makeup! I think I even did my hair twice this time and I know I spent a lot of time checking every detail. Right down to how the garters were fastened. I hadn’t broken in the heels so I spent every minute after breakfast in them. By six o’clock my ankles and calves were killing me! But, the 4” heels not only accented my legs and backside well but…they had a killer sound.In the end, for a forty-something brunette with average ‘tits’, I didn’t look half bad. The skirt was very lightweight and, if I moved and positioned myself just right, the minimum outline of the ‘lower’ lingerie was just barely visible. That was the idea.When Jack arrived I knew right away that he liked what he saw! I posed a little and strutted for him. I wanted to make sure, damned sure, that he approved…I’d nailed it and that made both of us very happy. A little kissing and feeling later I stopped him before he started to maul me. Even before we stepped out the door I made damned sure that I was thinking about my every move and gesture…I was in ‘girl’ mode for the night and loving it! I didn’t want to do anything to come even close to fucking this night up!Of course, if someone gawked, I could still ‘tease’ with discretion. That was allowed.Jack had actually made a reservation for us and requested a special table. When we arrived he parked a little distance from the entrance. I was a fucking bundle of nerves but he opened my door like a gentleman and handed me out so I gave him a little ‘flash’ to prime the pump. I then took his arm and strutted my ass off as we walked. When he held the door for me then followed me inside I had a case of nerves but worked at calming myself. We stood and waited until the waitress came to get us then followed her to a table that was nicely positioned. There wasn’t a crowd but about a dozen people there…we were given a few passing looks but no one stared openly at me which was good. As the gal seated me she bent quickly and whispered ‘Hon, you look great!’ then seated Jack. I was glowing, Jack missed it completely. Jack ordered for both of us only asking me a few times if this or that was okay. Everything was; he got us a nice bottle of wine to sip at while we waited, talked and relaxed. As the waitress had taken our order she was standing behind Jack a little. She appraised me a few times and gave me some smiles and winks which I thought was very nice. She brought us water and the wine then left us alone. In a few minutes I looked past him and not only was she standing in the door to the kitchen, with the other waitress, but one of the cooks was also there. The other gal gave me a smile of approval and waved…I waved back with a little discreet gesture. This really put me at ease and sort of set the tone for the evening. It also got me a few stares from other patrons who’d seen this happen. There was one woman, probably in her 50’s, who looked, said something to her husband then, a few minutes later rose and walked past us to the bathrooms. She had openly looked me over on the way, didn’t stay long then stared again on the way back. Yep, she was checking me out.Once seated again she said a few things to her husband…he turned and stared directly at me.That was about the time our salads came. It was funny because the other waitress brought them – she’d wanted a look – I got another approving wink and Jack got a playful kaçak iddaa jab on the shoulder as she walked away.About half-way through the salad I felt the urge to pee coming on. I excused myself and slowly walked to the toilets. You don’t think about something so simple until you’re dressed. Find a booth, close the door, check to see if there’s paper, reach up under the skirt and pull your panties down, hike the skirt up around your waist and pull most of it around into your lap, pee, milk a little and wipe……then, as you pull the panties back up tuck and arrange ‘everything’ so it’s hidden, pull the stockings up a little, check the garters, arrange the belt a little and lower the skirt while ‘fluffing’ a little. Do a quick check in the mirror on the way out (wish the ‘mens’ had a full length like the ‘ladies’) wash hands and flounce back to the table. As you sit remember to run your hands down the back of the skirt and tuck it under your bottom then slowly slide in. In this case, since I seemed to have an audience, I put my hand on Jacks’ opposite shoulder as I walked by. Ran it up and across his collar, down the other arm then sat. We had time so I asked him to refill my glass while I found a smoke and lit it, tilted my head up and slowly blew the smoke out. I put the cig in the ashtray long enough to shake the napkin and put it back in my lap while smiling across the table at my lover.We ate we talked we briefly held hands across the table and just enjoyed ourselves for a good while. As we finished Jack asked for another glass of water and coffee for both of us. While the waitress went to get it he took the bottle out of it and put two little blue pills on his napkin. I joked, “Hon, maybe I’ll have a headache later?” With a sinister smile he replied, “Then I’ll just have to **** you.”Our waitress arrived with the things and didn’t miss the pills. As she set my coffee down she bent and said “Looks like you’re gonna’ get lucky tonight babe.” Jack gave both of us a queer look as she set his things down, chuckled and walked away. When he asked me what the joke was I said, “Jack dear…the pills are hard to miss on the white napkin.”We got her back to order a little dessert. When she brought it and had set it on the table she said with an impish smile, “I hear Viagra goes great with cheesecake.” That broke all three of us up and had Jack blushing a little. She was being very nice and a little raunchy; in the process making us feel accepted and very comfortable. On the way out our waitress walked a few steps with me, took my hand and gave it a nice squeeze. She told me that I looked very good and it looked like Jack and I were very happy together…we were. She then gave me a little hug and whispered in my ear, “You’re lucky ‘girl’…wish I was gettin’ laid tonight.” On the way to the car Jack held my hand. When he opened the door for me I hesitated, turned to face him, got up on my toes with my arms around his neck and gave him a big messy kiss. He reached down and grabbed both of my cheeks to lift me a little as we kissed long and hard. As I ground myself against him I realized that the kiss wasn’t the only ‘hard’ thing about him so; slipping my one hand down to his bulging cock and rubbing a little I said, “Hon you better take me home and fuck me!”I teased him all the way home. By the time we parked behind my apartment he had a bulging raging erection that was threatening to bust out of those slacks. His whore had a wet spot in ‘her’ new panties and a major ‘itch’ somewhere else that needed scratched good and hard! We got as far as the couch…the first time.I pushed him down on it…just like a bitch in heat…straddled him and sat down. When I grabbed his hair his hands went straight up my skirt and right to work. I knew very well that everything he found there was going to really raise his blood pressure. While we kaçak bahis tried to suck each other’s lungs out through our mouths I got groped very well and his rock hard cock got well rubbed. With one last quick kiss I rose and slipped onto the floor on my knees, ripped at his belt then his clasp and then the zipper and his shorts. Once I had his cock out I simply dove on him taking as much as I could manage…he was awesome!For the next few minutes I worked at getting him as slick with saliva as possible. I also pumped away trying to squeeze a little pre-cum up and out. This one was going to hurt but that’s the way I felt then…I wanted to feel skewered…I wanted to feel ****d…I wanted him like the first time he’d slammed me against the wall in the bookstore and fucked me rough and hard! I got up and straddled him again. As I got in position over his cock I reached under my skirt, grabbed the crotch of my panties and ripped it to one side then, spit some saliva in a few fingers and rubbed it around my rectum. Jack had put his hands under my skirt and had my cheeks firmly in both hands. As I eased down on the head of his cock and it penetrated me a little he pulled my cheeks apart…I took a deep breath and sat down hard! As I forced him in his hands moved to my waist and he helped push me down…HARD! I saw spots, my eyes filled with tears, I slammed my face into his shoulder hard and that breath came out in a scream! I pushed hard like I was having a BM, rose on my knees and sat down hard again. The scream was because of the pain I’d felt during the hard penetration but…oh Christ…it was also because sometimes you just need that…it felt sooooooo good!I rode him as hard as I could bear while screaming yelling moaning and gasping my ass off. We also covered each other with continuous kisses while it lasted. I got my blouse ripped open, my necklace ripped off and the panties ripped apart in the crotch…all the better to ride him! In the end I got as much of that beautiful cock buried in me as possible, wiggled around on it and shared a very long hot kiss while he pumped a nice big load of cum in me. That cock of his, twitching like hell in my ass felt fantastic as he unloaded!The nice thing about pure lust and 100mgs of Viagra is that he stayed hard as a fucking rock. I got off his lap grabbed him by the cock and we headed for the bedroom. While Jack got out of his shoes pants and shorts I grabbed some lube and got my ass in bed. I got on my back, pulled my knees way up and spread my legs while getting the skirt up above my ass as I rolled back. I then grabbed his cock and made damned sure he found my waiting hole while I arched my back hard. His first hard thrust went in deep and all the way to the bottom of me. I got my legs around him, hugged him as tight as possible and urged him, “Fuck meeee honey…oh god…fuck me good and hard!”Something like an hour later and, several changes in our positions plus one good orgasm of my own, I lay on my stomach while he straddled my ass and pounded away deep and slow before blowing another nice load in me.After he pulled out we just relaxed and recovered a little. My gaping hole was raw and aching, I was a little sore inside but…glowing all over. We hugged kissed and played a little coming down from our sexual high. Following one very nice loving kiss Jack said, “You know…I love you.” I placed two fingers on his lips and replied, “That’s sweet lover but, don’t say that…it can’t happen…no matter how much we may want it…it won’t work.”We spent some time talking and kissing and talking and playing…and talking. Then more very passionate kisses……before I cramped-up bad, really bad then released a really long and wet air fart. We both laughed like hell before I grabbed his cock gently…damn, he was getting hard again!…and whispered before biting his ear, “Let’s just be happy with what we have and enjoy it?”We did. It was my turn to get out of the damned skirt, take off the blouse, push him onto his back and mount that cock! Like a good slut I rode him as hard as I could (kinda’ long too) until I brought him to another nice orgasm.