Chapter 4

Sandra

I went to the salon after work, and they styled my hair. I got home and took a shower wearing a shower cap, and then I went all out. I found my most stunning black evening gown and did my makeup up to the nines, and I was ready to go. I got in my car and drove over to the Florentine restaurant. Robert asked me to meet him at 7 pm, and I decided to wait a few minutes, so at 7:10 I entered the restaurant. Robert was waiting for me and smiled when he saw me. He walked over and kissed me. Robert looked so handsome in his 3-piece dark blue suit.

When the Maître d' led us to our table, I saw many other diners watching us as we walked by. We were seated by the Maître d', handing us our menus. I noticed the menu had no prices for the entrées.

Robert smiled and said, “I guess you don’t need to know the price. You only need to be able to afford it. So how are you tonight, Sandra? You are looking stunning, by the way.”

“I feel great, Robert. Until you called, I wasn’t sure if you ever wanted to see me again, but here I am.”

He ordered a bottle of wine for us and a plate of antipasto. We sat sipping the wine and enjoyed the delicious appetizers.

“I first want to apologize to you, Sandra, and I didn’t mean to put you through the wringer like that. I was in a place I had never expected to be, and I was able to make it through to the other side. My oldest friend told me I was an idiot if I didn’t continue seeing you, and I realized he was right. Everyone I spoke to told me that I would be a fool not to continue dating you. I am fortunate to have such open-minded friends.”

I thought, “I would enjoy meeting his friends and thanking them.”

Robert continued, “You are the best thing that has happened to me in a long time. You are nothing like my ex-wife, thank God, and I love being around you. When I look at you, all I see is 100% woman. I don’t care who you used to be, and I only care who you have become.”

I was relieved when I heard Robert say this. I knew he had gone through a ton of soul searching to get to where he was now.

“I’m delighted you want to continue seeing me. I have dated many men since I came out as trans, and you are the first to make it past my being transgender. You are indeed an exceptional man to me, and I love you too.”

We ordered our meals, and I don’t even remember what I ordered. I was just ecstatic that Robert was dating me, and my head was in the clouds. We chatted the rest of the evening, but we made sure not to close the place. Robert asked me if I wanted to see his condo.

“It’s nowhere near as fancy as your place, but it’s home to me now.”
I was intrigued, and I decided to follow Robert home.

I parked beside Robert in his underground parking, and we both went up to his suite.

“It’s not much, I had to get a place on short notice, so I leased this one.”
He opened the door to his place, and it was lovely. We walked out on his balcony, and it had a great view of the downtown. His home had an open concept floorplan with the kitchen, dining room, and living room in one large area. He held my hand, then drew me closer in an embrace and gave me a passionate long French kiss. I was trembling, and my passion was building.

“It’s getting a little chilly out here. How about we go back inside, and I can turn on my gas fireplace to warm you up.”

We walked back inside, and Robert flipped a switch, and whoosh, the fireplace started up.

“Let me get us some wine; please have a seat on the sofa.”

I sat down, and Robert brought out a bottle of red, and a couple of glasses, as well as a cheese plate and some crackers, in case we got hungry. I placed cheese slices on a couple of the saltines, fed one to him, and nibbled on the other. I took a sip of the wine, and it was a very smooth Bordeaux.

We embraced for a while, and he whispered to me that he missed me so much and was happy we were together again, and we kissed some more. He smiled at me and leaned in for another kiss.

I could feel Robert getting harder, so I opened his trousers and pulled his rigid member out. I got down on my knees and proceeded to suck on the head of his shaft and tasted his precum; with the wine, it tasted great. I continued to suck his cock and swallowed his shaft balls deep while fingering and licking his balls too.

After a few minutes of this, he couldn’t stand it any longer and told me he couldn’t hold back. I swallowed his shaft down my throat, and he proceeded to fill me with his cum. I enjoyed every drop and sucked on him until he became soft.

Robert then told me it was my turn. He stood in front of me and helped me remove my skirt, and pulled down my panties. He told me to lay on my back on the sofa. Rob got on his knees and then went down on me. Robert had a great tongue, and he soon made me orgasm. I removed my bra and let my girls out. Rob moved up and started to kiss and suck on my nipples. He nibbled on my nipples with his teeth, and my reaction was incredible. It felt like shots of electricity were exploding from my nipples down to my pussy.

Then he dropped down on me again, and he began using his fingers to massage my nipples as he explored my pussy with his tongue and lips. The tsunami was building in me, and it finally crashed, resulting in an extended orgasm. The feeling was so intense I almost blacked out; it was so powerful.

Robert then stood up and took off his shirt and pants and laid on me, and we kissed and embraced each other. He slowly entered me with his cock, and I was glad I had lubricated my vagina before leaving my house. He smoothly slid into me, and I felt his cock become harder as he began to pump in and out of my pussy, all the while kissing me and playing with my nipples. I was going crazy and started to rub my clit, and it felt so good. I didn’t want it to stop, and I was moaning louder and louder as he was pumping me hard, slamming his cock in and out of me, in a very hard fuck. I just kept saying harder and moaned louder.

Another tsunami hit me, and I began to scream, and Robert covered my mouth with his lips to keep me quiet as I continued to scream in ecstasy. Robert exploded inside me, and I felt his cum fill me up, then he collapsed on me, and we were both breathing heavily, trying to recover. He kissed me again, and we embraced while lying together.

Robert smiled at me and kissed me again. “You are lovely, you know. I am so glad we met, and I realized how much I love you. I don’t ever want to leave you.”
I kissed him back and smiled. “I have fallen for you as well, and no one has ever made me feel the way you make me feel.”

We both smiled at each other and kissed again. Robert asked me if I wanted to take a shower with him. I was all hot and sweaty after our erotic workout and followed him to the bathroom. I stripped off my stockings and garter and followed him into the shower. It was easily large enough for two, and we took turns soaping each other up and washing off. I was soaping up his tool, and it began to get hard in my hands.

Robert pushed me against the wall and entered me again. He fucked me hard this time and held my wrists against the wall as he pumped his entire length in and out of my pussy. He nibbled on my tits, and I orgasmed again as he came in me a third time. We then stood under the shower and rinsed off while kissing and embracing each other. I rinsed him off again, and I rinsed out my vagina with a handheld showerhead. We kissed a little more and then got out of the shower and toweled dry. I wrapped a towel around my hair. He handed me a beautiful silk robe.

Wow! Where did you get this? He smiled and told me he bought it for me to have something to wear after we showered. I kissed him again and told him how thoughtful he was. I looked in the mirror, and the robe was beautiful. We kissed again and then went back out to the living room and sat cuddling in front of the fire, chatting as we finished the wine, cheese, and crackers.

“It’s Friday, so I am hoping you were planning on staying overnight.”

I kissed him and told him that the thought had occurred to me. Robert turned off the fire, and I followed him back to his bedroom, and we snuggled up beside each other and chatted until we both fell asleep.

We woke up in the late morning; Robert got up first and started the coffee in the kitchen. I went to the bathroom, and I could smell the coffee when I came out.
Robert was busy making some bacon and eggs for us, and he did a reasonable job while I buttered some toast. We sat beside each other in front of his breakfast bar on a pair of stools. We ate breakfast and enjoyed our coffees.

“So, Sandra, what would you like to do today?”

“I haven’t given it much thought yet.”

“Do you like golfing?” Robert asked.

“I have golfed in the past, but not too much lately. It sounds like an excellent way to have a lovely afternoon outside.”

Robert added, “I have a membership to a golf club if you would like to go for a round of golf today.”

“I would have to go home to change into my golf clothes. I can take a shower here and then head for my place. How about you swing by and pick me up in an hour?”

“That sounds like a plan,” said Robert.

After breakfast, we showered together, and I changed back into my dress. We kissed goodbye, and I left for my place.

I got home, changed into a cute golfing outfit with a white top and a pink mini skirt, and brought my set of clubs up to the front.

Robert soon knocked on the door, and he picked up my golf bag, and I followed him outside. He placed them in the trunk, and we got in his car, and we were off to his golf club.

“You look great, Sandra; I love your outfit. And your golf set, a white bag with pink trim, it suits you completely.”

I smiled and kissed him, and we were off to his country club.

We checked into the club, and we soon had a tee time along with a golf car. Robert teed off first since I was playing from the lady’s tees. He hit a long drive with a slight fade down the first fairway, and I complimented Robert on his shot. We got in the cart, and Robert drove me over to the lady’s tee. I set up, teed up my ball, and hit my drive about the same spot as he landed.

“That was an excellent shot, Sandra!”

I blushed and said thanks. I always used to play golf when I was still a man, but after I transitioned, I almost gave it up. I was unable to hit a ball straight. My balance was off, and my boobs were now in the way of my swing. I had to start over, and I took lessons on playing golf like a girl. The golf pro adjusted my swing to compensate for my new figure, and I started to hit the ball squarely again. I lost around 100 yards on my drive, but I was now a lot weaker than I was as a man, and I was happy to use the lady’s tee.

We got up to where our balls had landed, and I was first up. Robert told me it was around 150 yards to the green from here, and I got out a six iron. I lined up and hit my ball; it flew beautifully, dropped, bounced in front of the green, and rolled up on the apron. Robert told me I had a great approach.

He walked forward to his ball, and I think he used an eight iron. He swung, but the wind caught his ball and pulled it a bit to the right, and it landed in a sand trap beside the green. He winced, and I just laughed and told him he could now show me how good his short game was out of a sand trap.

We drove up to the green, and I got out my putter, and Robert took out his sand wedge and his putter. I looked at the pin, and I had a long 30-foot putt from the front of the green. Robert was pin high, and he walked around behind the trap and took another look. He got down into the sand trap and took a half swing, and in a big cloud of sand, his ball came out and landed on the green, rolling to about 6 feet from the pin. “Nice shot,” I told him. He gave me a big smile as he was happy about it too.

I walked over to my ball, and I marked it, picked it up, and cleaned it off before replacing it on the green. I was still using my trusty old Ping putter, which I had used for years. It was the only club left from my old set, as I had replaced the rest with a woman’s set, which had worked better with my new golf swing.

I lined up my putt and practiced my swing a couple of times and then sent it up the green towards the hole. Luck was on my side, as I had hit it a bit too hard, and it dropped into the hole, much to my amazement! Robert clapped when it went in, and he told me it looked like he had his work cut out for him.

He lined up his putt and tapped it towards the hole. There was a ball mark which we hadn’t noticed, and it caught his ball and sent it to just beside the hole. He tapped it in, smiled at me, and told me I had a birdie on that hole, and he had a bogie.

The second hole was a par three short hole, and I was up first. The lady’s tee was ten yards after the men’s tee. I walked up and took my nine-iron and hit the ball beautifully, and it dropped pin high on the green. Robert complimented me on my shot, and then he teed up using his nine-iron. He hit his ball, and it landed on the rear of the green, and the backspin made it roll back towards the hole, stopping around 5 feet to the pin.

“Wow, Robert, that was some great backspin you had there.”

We got in our golf cart, and Robert drove us up behind the green. We both got out our putters. I looked at my ball, and I had a 4-foot putt to drop it in. I marked my ball and let Robert go first. He was able to sink his putt from around 7 feet, and I clapped. I walked up and placed my ball on the green, lined it up, and tapped it towards the hole. It first looked like the ball would stop short, but it had just enough momentum to drop in. I felt relieved and retrieved my ball, and we were off to the next tee.

We played our way through the front nine of the course. And on the ninth hole, we were both tied at two-over-par. I had an awful time on a par five and had squandered my lead, but that’s golf, you never know what will happen, so there was no use worrying about it. It was Robert up first, and he hit a tremendous drive down the middle of the fairway. We drove up to the lady’s tee, and I took my driver and ripped my best drive of the morning, and it landed about 10 yards ahead of Robert’s ball.

“Damn Sandra, you keep getting better. We both have had a great game so far today, and you know what you are doing out here.”

I think I had impressed him so far, and I smiled.

We drove up to Robert’s ball, and it was around 180 yards to the hole. He pulled out a fairway wood and struck the ball beautifully towards the flag, and it landed on the apron of the green and rolled up to about 15 feet from the pin.

Not to be outdone, I also took out a fairway wood, and I struck my ball and watched it head for the flag, and it dropped on the green about the same distance away from the hole as Robert’s ball. We drove up to the green, got our putters out, and looked at our upcoming putts. I was first, as it looked like I was a little further away from the hole. I lined up my shot and took a couple of practice swings. I sent it towards the hole, and it dropped in! I cheered, and Robert clapped in appreciation.

I retrieved my ball from the cup, and it was Robert’s turn. He had to sink his putt to tie my score. He hit his putt, and it got to the hole but rimmed it and stayed out. That was a tough break, Robert, as he tapped it in for a par.

I ended up at one over par for the front nine and Robert as two over. He grinned at me and said, had I known you were this good at golf, I would have asked to go on another hike instead. I gave him a big smile and kissed him, saying, but you would have missed all this fun with me here.

We stopped at a snack shack on the way to the back nine, and we both had a hot dog and a soda. I told Robert he would have to step up his game on the back nine if he wanted to win against this girl, as I have always been competitive when it came to golf. He laughed and said, I certainly have my work cut out for me. We finished our quick lunch and continued to the tenth tee.

We enjoyed playing with each other on the back nine as well. I had some fun with Robert, distracting him on the tee by dropping my ball and then bending over to pick it up just as he was setting up his swing. He laughed and told me it’s not going to work, girl, so I blew him a kiss.

He still got off a reasonably good drive, but I outdistanced him from the lady’s tee with my shot. He laughed and told me maybe I should be playing from his tee instead. I gave him a sly look and told him, nope, it’s the lady’s tee for this girl.
We tied the tenth hole and kept pace with each other through the back nine until we got to the eighteenth tee, and we were both tied.

Robert swung first, and he had a blistering drive down the fairway. I hit my ball from the lady’s tee and wound up beside him. We drove down the fairway, and I got out my fairway wood and smashed the ball on the green, just below the pin.
Not to be outdone, Robert cracked his shot pin high on the green. We drove up to the green, and he marked his ball and let me go first.

I marked my ball, cleaned it off, and placed it back on the green. I lined up my putt and made a few practice swings, and struck the ball towards the hole. I had a 30-foot putt, so I didn’t think the ball would go in, but it wound up 2 feet from the cup.

Robert then lined up his shot and stroked his ball into the hole for a birdie. I tapped my ball in for par, and he beat me by one stroke.

I laughed, saying, “I will beat you on our next time out.”

He grinned and said, “What makes you think I want to play golf with you again?”

He smiled and added, “You are too good a player, and I might lose against you.”

“What’s the matter, Robert? Afraid that a girl like me will beat you at golf?”

Robert just laughed and kissed me, saying, “That was a great game we played, Sandra, and of course, I want to play with you again. My ex-wife hated golf and wouldn’t have been caught dead out here with me.”

“That was her loss,” I replied.

We returned the cart, put our bags in the car, and removed our golf shoes. Robert invited me into the club’s restaurant. We walked in, and a few guys he knew walked over and greeted us. Robert introduced me to his golfing buddies, and I shook everyone’s hands. He told them that I had almost won out there today, and he barely squeaked out a win against me. They laughed and invited us over for a couple of drinks. We ordered a couple of beers, chatted with his friends for a while, said goodbye, and walked over to the restaurant. It was a nice place, and we both had a great meal there. I had a roast chicken dinner, and Robert had a steak.

I told Robert he had some good friends there, and this was a friendly club to which he belonged. He agreed and told me, no one is pretentious here; we like to play golf and enjoy ourselves.

We finished our meal and headed back into the city. Robert drove me back to my place and helped put my clubs away, and I started the coffee going.
We shared a coffee and a few cookies. I then asked Robert if he wanted to shower after our game, and I would help scrub his back. We went up to my bedroom and helped each other undress.

We headed for the bathroom and started our shower. I soaped up Robert, and he did the same for me, and we took special care with each other’s equipment. I gave special attention as I cleaned Robert’s balls and stroked the shaft of his club. I was washing him down, and he kept getting harder and harder. Rob pinned me against the wall and slowly entered me as he French kissed me under the shower.

I moaned a little as he started to pump his cock into me slowly at first but then building up his speed. I kept kissing him, and Robert exploded inside me as I shook from an orgasm. We continued to kiss until he lost his erection, and I cleaned him up and rinsed myself out. We got out of the shower, dried each other off, and dried my hair with a blow dryer. I told Robert I needed to do a few more things to get ready and told him he could wait for me in the bed.

After Robert left the bathroom, I gave myself a douche to clean out my bum, and I also placed lube in both of my holes down there. I walked back to my bedroom and snuggled beside Robert to continue our lovemaking in the bed.

Robert went down on me, and his lips and tongue continued to amaze me down there. He pinched my nipples and massaged them with his hands, and it sent shivers and what felt like bolts of electricity through my body.

Once again, the tsunami was building, and I shuddered when it hit me, as I exclaimed, “Oh God yes!”

He slowly regained an erection and asked me, “Have you ever tried anal?”

I grinned at him and said, “I thought you would never ask. I am all primed and ready for you.” I handed him a small bottle of lube for his cock.

“I have never done this before, so let me know if I am doing it wrong.”

Robert put some lube on his hard cock. He smiled at me and pulled my legs up in the air. Robert leaned on them to raise my bum and slowly maneuvered his cock against my hole. He slowly pressed into me. Rob got the head of his cock inside me and asked me how I felt. It hurt me at first, but I was fine now, so he went in another couple of inches and stopped. He pulled right out and then went in again, this time almost all the way, and held it there. I made a gasp, and I felt so filled up. He then pressed in all the way. And he kept it there for a bit.

“Are you ready?”

“Yes.”

Rob then proceeded to slowly fuck me with his entire shaft, pulling almost out, and then went in balls deep. It felt great. The first guy I dated when I was transgender was a bisexual guy; it didn’t last, but I hadn’t yet had SRS, and he fucked me in my rear pussy. I knew what to expect, and it had been a couple of years now, but I still enjoyed this feeling. It was almost the same as being fucked in my pussy, but not quite the same. By this time, Robert had started to fuck me harder, and he was pounding my ass cheeks, and I could hear the thwap of his thighs slapping my ass as his balls hit me too. I started to moan, and I kept getting louder, and when I began to scream with pleasure, Robert silenced me by leaning forward and french kissing me. I guess I was getting too loud for him. Robert continued to kiss me until I orgasmed, and he came in me. He collapsed on me, panting and out of breath.

He grinned, saying, “That was great!”

He pulled out, and we laid beside each other while caressing and kissing each other. It was getting late, and I turned out the lights, and we both drifted off to sleep.