Sarah and Greg

by GR

Copyright© 2014 by GR

Erotica Sex Story: The story of how Greg and Sarah met and fell in love, despite Sarah's deep secret.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Shemale   Fiction   Light Bond   Oral Sex   Anal Sex   Masturbation   .

Greg hated everyone and everything as he was getting soaked by the pouring rain. More accurately, he hated Diane, and everyone and everything which reminded him of her. Right now, this included every person he saw, every place he imagined, and everything that came within his field of view. Greg felt like he had been kicked in the stomach, or perhaps a little lower. He so wanted to cry, and even though the pouring rain would cover his tears, but it would not cover his inevitable red eyes. Anyway he had been raised to believe that men do not cry in public. He wandered from Diane's apartment to his own, lost in thought and on the verge of ... something. He knew he was within a block of his own apartment, but he was already drenched, and at the moment, he didn't care about much of anything, so instead of turning right at the corner, he went straight and crossed the street, not bothering to look if there was any traffic; fortunately, there wasn't.

Sarah was leaving work only a few blocks from her apartment. It had been so beautiful that morning, that she had walked in her business attire the three blocks. She didn't check the weather report, judged the day by its beginning and went to work as if it would be sunshine all day. Despite the suit she was wearing, she realized that she had to walk home in the downpour. She put her briefcase over her head, and ran, as well as anyone without practice can run in heels.

Greg kept his head down figuring he would walk around a few blocks and end up back at his apartment. As he rounded the next corner at the restaurant Francesca, he felt like he was punched in the chest, as he was knocked back a few steps. He looked at what just hit him, and unlike him, she had been knocked onto the ground. Also unlike him, she was laughing. He immediately went over and offered her a hand up. She looked up, still laughing, and extended her hand. Greg took it and helped her up.

"I am so sorry," Greg began.

"My fault. My fault. I wasn't looking where I was running," Sarah explained.

"Neither was I," Greg said while shaking his head. "I was in such a bad mood and hoping to walk it out." The rain continued, but neither could get much wetter.

"I'm sorry that you are in such a bad mood. Can I help?" Sarah offered with such sincerity, ignoring her own situation.

Greg was taken aback by this stranger offering kindness. "I know this sounds like a pick up line, but you are drenched more than I am and you got knocked to the ground. Can I at least buy you dinner?"

Sarah thought for a moment weighing the chances that Greg was a serial killer. That didn't seem likely to her. "Sure, why not? How about we meet here in an hour?"

"I will see you then" Greg smiled as they parted. He walked the rest of the way home in a more direct route, but was thinking all the way home, "Why did I do that? I just saw my still beating heart ripped out of my chest." Greg felt a mixture of anger, excitement, anxiety, frustration, ... He got to his apartment, stripped down, showered under hot water for about 30 minutes, then dried himself off as best he could with the towel, and lay on the bed to finish drying.

Sarah smiled the rest of her way home, feeling happy – and wet. She tried to whistle a little, but the rain running down her face prevented that. When she got inside her apartment, she stripped down to her skin, dried herself off, and sat on the bed, wondering what she should wear this evening. She stood up, walked over to her closet, flipped the light switch, and walked in. While deciding how she should look, she thought, "He was obviously upset about something, so I could go long-time friend – t-shirt, jeans; or like what I wore when we met – business attire, since he asked me out looking like that; or distracting – a low cut dress, showing my cleavage; or...". She paused mid-thought. She was going to go classic new friend. She reached up and pulled the white denim pants off of the hanger, light blue cotton button down shirt with a white, subtle, stitched logo over the breast. As accessories, she chose a light brown belt and some earrings, which had with a little bit of white, light blue, and brown. She went to her dresser and picked out white lace panties and bra – she didn't want it obvious what she was wearing underneath. She walked over to her mirror and held her shirt and pants up to her body to see what it looked like. She smiled and then laid the clothes out on the bed.

Greg rolled into a sitting position on the edge of the bed with his feet on the floor. He looked in the mirror and felt he looked like crap, but he obligated himself to this dinner. He looked in his closet, trying to decide what to wear. He saw a shirt he liked – white shirt with thin, vertical, dark-blue stripes. He smelled it; it was clean. "What pants does he have to go with them?," he wondered out loud, to no one in particular, "My jeans ... but they're dirty. What other shirts do I have? Clean shirts. There's the crazy 'puzzle shirt', but that's a bit much for a first dinner. Oh what the hell." He grabbed it, smelled it – it was clean – and then grabbed the black pants hanging nearby – also clean. He went to his dresser, opened up the middle drawer, and grabbed the first clean pair of underwear and put it on. He put his pants on, followed by an undershirt, then his shirt. He looked around for his belt – it was still wet from this afternoon. He went to his back-up belt – more beaten up than his work belt, but functional. He put it on, and then grabbed the first comfortable pair of clean dark socks which he found. He looked in the mirror and mused, "Meh. Good enough."

It was about 10 minutes before he was to meet her, so he left. Two minutes later Sarah left her apartment with her umbrella. One minute later, Greg returned to his apartment and grabbed his umbrella and left again. They arrived within one minute of each other.

Sarah smiled when she saw him. "I was wondering if you would show up, after this really bad day of yours." She paused. "I'm glad you did."

"I went back and forth several times but knew that I had invited you. I try to live up to that which I say I will do ... Some days better than others, though." Greg gave a weak smile, and Sarah understood that it was not her which weakened it.

"Shall we go in?" Sarah offered. Greg nodded and they entered into the waiting area of the restaurant. They tilted the wet umbrellas, shook them a little over the mat at the entrance, folded the umbrellas, and walked to the sign which read "Please, wait to be seated."

The hostess came over. "How many?" she inquired with a smile.

"Two," responded Greg, holding up two fingers.

"Right this way." The hostess led the way to a table in a slightly darker part of the restaurant, mistakenly thinking this was a "real date".

Greg's upbringing kicked in as he pulled the chair out for Sarah. She smiled and sat as Greg scooted the chair in. Then Greg went to the other side of the table and sat. He smiled at Sarah, although he wasn't thinking many happy thoughts.

There was a moment of silence before Sarah broke it. "I know today is bad for you. I was surprised when you asked me to dinner." Greg looked at Sarah trying to figure out how to respond. Sarah continued, "I figure I am here to listen or to distract – whichever you need at the moment. And I'm okay if your needs change from moment to moment."

Greg sat there, with moisture building in his eyes, feeling exhilarated and like crap at the same time. He was with a woman who was giving, who deserves better than he can give at the moment, but seems okay with whatever. Greg finally got out some words, "I'm sorry."

"For what?"

"For this date ... meeting ... therapy session ... whatever this is. My mind is trying to be here with you, but it will come and go."

Sarah looked compassionately at Greg, "I am here to break up my ordinary routine. Worst case scenario is that we don't talk for an hour, we eat, I go home, and tomorrow I get up as I would have otherwise. Best case, we become friends, and we do this again." Greg sat there in disbelief. It crossed his mind, amongst many other thoughts, that he was part of a lab experiment, but that quickly changed into a thought on the rain, and then on to other things. Sarah continued, "Do you want to talk about today?"

Greg paused for a moment knowing that if this were a real date, he would not talk about it, but instead, he took a deep breath, and said, "What the hell. I am going to dump a load of crap on you and treat this as therapy for me. If at any point you want me to stop, just say it. If you can't find the words, just storm out. I will understand." He waited to see if she would respond.

With a look like she was preparing for a hurricane to hit her at any moment, all she said was "Go for it."

Greg took another deep breath and started with, "Thank you." He then launched into a monolog about Diane and the bad break-up which just happened. He talked about how they met, how they were in love – or not – and how it ended. Mostly Sarah just sat there, smiled, and listened. Occasionally, she would react with the expected reaction – a small laugh, a look of horror, and the like. She just wanted Greg to talk it out. When the waiter would come over to see if they needed anything, Sarah acted as gate keeper, deciding sometimes that Greg needed to finish his story, in which case she would wave the waiter off, and in other cases allow him to approach. After a few hours, Greg felt like the whole meal had been cathartic. And the entire time, Sarah seemed indefatigable. She was genuinely interested in Greg's life, as she was in many other people; she enjoyed people.

As Greg was feeling better about himself, he stopped and finally said, "Sarah, thank you, but I want to know about you, and why you do this."

Sarah smiled, was silent for a moment, sighed, and replied, "You were in a dark place earlier, and I saw that; I just wanted to help. I think we are beginning a friendship here which I don't want to jeopardize yet." She paused for a moment. "I will make a deal with you," she smiled. "Let's meet again each day here for dinner for the next few days. We get to know each other under less dark circumstances, and slowly I will talk about myself more. Despite my eagerness to hear your story, I am less open about my own. This has hurt previous relationships, but I am working on it."

Greg agreed to the deal. They finished the meal, he paid, and they stood to leave. Greg and Sarah walked to the door the restaurant and stepped out; the rain had stopped. He was going through his options: wave, handshake, hug, kiss ... As he wondered, she offered her hand for the shake. Relieved, Greg shook her hand, smiled, and bid her, "Good night, thank you, and see you tomorrow at 6."

She smiled, "I am looking forward to it."

They met again the next night promptly at 6. The dinner lasted three hours during which they talked about the day, some stories from the past, and parting with a hug. As Greg walked home, he worried that she was just a rebound – that his feelings were not real. But at the same time, if he had met her earlier, he could not help thinking that his feelings would be the same. At this point, he knew that the worst case scenario was that he had a friend.

The next night was very similar: lasting about three hours, ending in a hug, and Greg and Sarah both feeling confused about what they were both feeling. Sarah knew she was still holding back, and wondering about how she drops hints at her deeper secrets. She knew it could not be in the restaurant or any public place.

On Friday, the fourth night, as the meal ended, and they parted, Greg went in for the hug, and she kissed him on the lips. He looked surprised. "Are you okay with the kiss?" Sarah asked.

Greg was speechless at first and then found his voice, "I have been thinking about kissing you since our first dinner." He stared at her, wondering if he could kiss her.

Before he could decide, she asked, "Would you like to come up to my place?" She felt that this was the time to let Greg in.

"Part of me would love to, and part of me is afraid of how I am feeling about you. I don't want you to be a rebound, and I definitely don't want to hurt you."

"Greg, I care about you, and I am starting to have deep feelings about you. I am usually very nervous about having people over, but it is time I let you in." Greg wasn't sure of her meaning of the last part, but decided it was metaphorical. Knowing that she was there for him when he needed to talk, he would be there for her to talk.

Greg smiled, "Lead the way." He took her hand and they walked slowly together the few city blocks to her place. While they walked, they talked little. She put her head on his shoulder as they walked, and it seemed natural to both of them. When they arrived at her apartment, she got her keys out, unlocked her apartment, and opened the door.

Just before she turned the light on, Greg had visions of dead bodies – she was a serial killer, or clothes everywhere – she was a slob, or small children – she was a mom, or ... The lights went on. Her apartment was very nice, neat, and as a rational person would expect.

"Would you care for anything to drink?" Sarah offered.

"No thanks."

Sarah walked over to the couch, sat, kicked her shoes off, and swung both of her legs up beside her into a lady-like knee bent pose. She patted the seat next to her for Greg to sit. Greg responded by sitting closely next to her. He realized how beautiful she was – beautiful inside and out. He was thinking that he might be in love with her.

There was a moment of silence, before Greg said, "I think I am in love with you." He paused to see how she would react – she seemed scared, but at least she did not recoil in horror. "I feel that you have something to say to me, and I will agree that no matter what you say, I will not leave without talking it through. I owe you that."

Sarah looked apprehensive. She looked into his eyes and said, "I think I love you, too." She leaned forward and kissed him on the lips quickly, like a good friend. He leaned forward for a more passionate kiss, when she put her hand up to stop him. Greg backed up and waited for the hammer to fall.

Sarah looked at Greg, then looked down. "Greg," followed by a long pause, "Is there anything that would cause you to stop loving me at the moment?"

He was taken aback by the odd question. "If," he fished his memory for what could do it, "you were serial killer," then paused to see how she responded but she just looked at him, "if you were trying to con me out of my money; if you got your thrills out of playing mental games with me." He could not imagine any of these being true. He looked at her; there were tears in her eyes.

"Well, none of those apply to me."

Greg breathed a subtle breath of relief. "What is it, Sarah?"

"I ... am not ... I am not who you think I am." Greg was about to speak when she put a hand up indicating that she wanted to finish. He could not imagine what she could be that would stop the way he feels about her. She continued, "I have had surgery."

After this there was a pause. Greg was trying to figure out what kind and being Greg, he tentatively asked, "what kind?"

"Cosmetic," she said slowly.

"and... ?" Greg queried, still confused.

"Breast augmentation."

Greg was still confused. "Is that it?"

"No ... Liposuction ... Facial reconstruction..."

"Had you been in an accident?"

"Only at birth."

Greg was really confused by this. "How so?" he asked slowly, still trying to figure it out.

Sarah took a deep breath, and blurted out "I have been a woman all of my life, but not every one agrees with that." She turned and looked at him, preparing for a violent reaction. She had been there before, only a few times, but enough to be very guarded.

Greg sat there processing what she just said. He was very confused at first. He knew she had revealed her big secret, but it was not obvious yet. After about a minute the possibility occurred to him. He finally spoke in a questioning tone of voice, "People don't agree because you were a girl and then a woman?"


"You have past lives?"

"No ... Uh, I don't know. That's not it." Sarah was hoping he would figure it out before she had to be blatantly obvious.

"You were born male?"

"Yes," Sarah drew back at her saying that, waiting for the punch.

Greg just sat there, trying to figure out how he felt about it. He started to speak a few times before finally getting a question out. "Are you a woman now?"

"I have always been a woman."

Greg got very serious. "I mean are you biologically a woman? Um," then he just cut to the question he needed to know now, "do you have a penis?"

Sarah got very calm, "Yes." She waited again for how he would respond.

Greg got up and started for the door, stopped, and returned. The look on his face was one of great concern. "I said I would talk this out." Greg wasn't mad or irrational as he returned; Sarah was relieved.

Greg got back to the living room and sat on a chair near the couch. Sarah remained on the couch. Again there was silence as Greg tried to figure out what to say, and Sarah waited for Greg to talk. After a three minutes, Greg inhaled deeply and then began, "I don't know how to process this."

Sarah tried to offer some insight, "Your knowing that I have a penis does not change who I am. You said you thought you loved me." She didn't want to press him, but she felt the need to say it. Greg nodded.

Greg eventually came back with "You're right." He paused and then followed emphatically, "but I am not gay."

Sarah looked hurt, but knew that because they were still talking there was hope. "I am a woman who happens to have been born in a man's body. I look like a woman, I dress like a woman, I talk like a woman. I have a woman's mentality and a woman's heart. Just because I have a few different biological parts does not mean that I am not a woman." She was still fuming over the 'gay' comment. Her voice was still controlled but louder than before, "Also, so what if you are gay or not! Does your sexual identity define you? Does it make you good or bad? Gay is not a choice, just as the body we have is not a choice."

Greg saw her point. He stood up to leave. "I do care about you, but I need to come to terms with this." He walked to the door. As he reached down to the door knob, he asked, "May I call you later to talk things out?"

"Of course!" Sarah exclaimed with tears welling in her eyes.

Greg left leaving Sarah in a state of hope and sadness. He walked down the hall to the elevator. He thought to himself, "Why didn't she say something sooner? ... How could she? ... How could she have done it differently?" He got to the street and started walking – not necessarily home. The night air was cool, and surprisingly fresh for a city. He walked quickly and in thought, but he was still able to avoid running into anyone or any thing. As he walked, a sadness crept upon him. He thought about how incredible the last few days have been, how he looked forward to talking with Sarah, ho whis heart skipped a beat when he saw her, and how excited he was by the kiss. He didn't want to lose that.

He then stopped and asked himself, "Do I want to be just friends with her?" He noticed he still thought of Sarah as a 'her'. After a minute or two of standing in the middle of the sidewalk, he came to an answer, so looked to get his bearings, turned and headed back to her apartment.

Sarah calmed herself after Greg left. Deep breathing exercises, calm music. Telling someone had always been tricky for her. She still wasn't sure how to do it well. This time had not been a horrible failure, but her fantasy of how it would go never came to pass. When she would think about never seeing Greg again, tears would well in her eyes. Slow, deep breath. Good air in ... negative energy out. Good air in ... negative energy out.

She got up and went to go shower. She closed the bathroom door and started the water. She continued to breath deeply to calm herself as the steam started to rise above the shower curtain.

Then Greg got back to her apartment and knocked on the door. Sarah was about to step into the shower when she thought she heard something in the other room. She decided it was the neighbors and finished stepping into the shower. The water felt good on her body.

He waited, but there was no answer. He suddenly became worried. Had she done something to herself?

He banged again, this time louder. Then she heard a noise again; this time louder. She drew back the shower curtain and listened. She couldn't hear anything other than the water running. She turned the water off, stepped out of the shower, and put on her robe.

Upon no response, Greg turned and headed slowly to the elevator.

Sarah got to the door and looked through the peep hole. No one was there. "It must have been the neighbors," she thought. She turned to go back to the shower, when she decided she needed to make sure. She opened the door and poked her head out. No one was at her door, but she heard the elevator bell ding as it arrived at her floor. She heard the doors open and start to close. On a chance, she called out, "Greg?"

The elevator doors open again, and she saw Greg running back down the hall toward her. She stepped back into her apartment out of reflex, but she didn't close the door all the way. She stepped back as Greg pushed the door completely open, stepped toward her, took her in his arms and kissed her passionately.

Their lips embraced as they pressed their bodies together. Without stopping the kiss, he closed the door with his foot, then turned her, and pressed her against the entrance way wall. He opened his mouth a little, and she followed suit letting the tongues meet and explore. He worked his hands inside her robe and felt her uncovered skin. His hands wrapped around her, as hers found their way under his shirt. She felt his abdominal muscles and then worked her way up to his chest. She felt his nipples and soft chest hair. Her thumbs briefly played with his nipples, before she worked her hands around to his back, tightening the embrace and the passion of the kiss.

He broke off the kiss and looked deeply into her eyes. He smiled and kissed her again. He stepped back and looked at Sarah's exposed body, as her robe was pretty much covering only her arms and back. He sighed with a large breath. She waited for him to speak, knowing that after the initial moment of passion, blood might be flowing back up to his brain. Greg broke the silence with a quiet, "I love you. I need you in my life."

When Sarah smiled at this, he stepped toward her, kissed her, and moved his hands up to push the robe off her shoulders and onto the floor. In kind, she pulled his shirt up to his chest and then let him take it off the rest of the way. While he was taking his shirt off, she undid his belt buckle, unbuttoned his pants, unzipped them, and pushed his pants and underwear down past his hips. They fell easily to the floor, and he stepped out of them. Feeling a little foolish standing there in just his socks, he quickly lifted each leg and removed his socks, letting them fall to the ground. They embraced again, and went back to kissing feeling their naked bodies press against each other. He loved the feel of her breasts against him, and although new, he enjoyed her cock pressed against his. She loved the feel of his hands on her, of his moment of commitment to her. She wanted to cry with joy, but was swept up in the passion of the moment, and the ecstasy she expected to be coming soon.

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