Chapter Two
As they traveled back to Minnesota, it was a bit solemn and sad, leaving Sam and Lilly behind, for they both knew they were returning as Mother and son.
Walking through the terminal to get their bags, Lilly’s phone rang.
It was her mother calling, saying, “Your Dad was taken to the hospital.”
They drove directly to the hospital, seeing her Mom in tears, she just said, “Your father passed away. He had a massive heart attack.”
At the funeral, Sam was amazed by the large number of people who attended to offer condolences, and thanked them for everything his grandfather had done for them.
Sam held his grandmother's arm and leaned to her and whispered, “I was ashamed that I really didn’t get to know him for his humanity.“
His grandmother patted his hand, saying, "He loved you as his own son, Sammy. We both were thrilled to see you grow up into a young man."
One evening, several days later, Lilly sat quietly in deep thought. Sam let her lie on the sofa while rubbing her feet, enjoying the simple comfort of being together.
Lilly spoke up, “Sam, I want to share some more with you."
They went downstairs to the garage, where they stored things. She opened a Christmas box and showed him the crystal decorations her father had made. Then, she opened a small green box. Inside was a perfectly crafted crystal angel.
Sam said, “I remember this from long ago, you would hang it up in the window.”
Lilly remarked, “That was one just like this one.” Your Dad had a temper tantrum, threw the other one, and broke it. I picked up all the pieces, sent them to my Dad to fix, and told him what happened. When we moved back here, Dad gave me this new one.”
Lilly further explained, "My Dad made several of these, and he gave them to people who deserved a special reward.” Lilly held a flashlight up to the angel, and it spread colored light all over the garage.
As the light reflections sparkled over the surrounding area, Lilly mentioned to Sam, “I saw one just like this on eBay years ago, with a $1500 reserve. Dad bought it for $2000 and returned it to the person who desperately needed the money. That explained to me the man he was, not the father he was. Every time I hang this at Christmas, it reminds me of that occasion."
Sam and Lilly went back upstairs and went to bed that night. Lilly was crying tears as they embraced each other as partners dealing with a loss.
Lilly whispered to him, “I love you, Sam.”
Sam whispered back, “I love you too, Lilly.” They both fell asleep in each other’s arms, knowing their secret stayed behind the walls of the apartment.
Lilly and Sam continued to model lingerie and seductive outfits as they took dozens of photographs together, some for fun, Halloween, but mostly they enjoyed cosplay outfits together and attending cosplay events to conceal their love for one another and be in public.
Lilly’s best friend, Jackie from work, lived across the street. Jackie would visit frequently and enjoyed cosplay costume events. They promised never to disclose this to their grandmother, for she would not understand.
Lilly had transformed Sam from a young ‘wet behind the ears’ boy, to a refined, chivalrous man. To many, he seemed like ‘a gentleman of the bedchamber’, and all the while no one ever knowing their secret love for one another, except maybe Jackie.
One year later
It had been almost 3 months since Lilly died from a heart condition called Cardiomegaly, or simply an enlarged heart. Lilly had been treated for high blood pressure for years, which was complicated by catching pneumonia, and she died of a massive heart attack.
The months after Lilly’s death marked Sam’s lowest point. His father neither attended the funeral nor sent condolences. From then on, Sam vowed not to be as distant as his father. If it were not for Jackie explaining to him, many people would distance themselves from their children from past marriages. Sam felt something special for Jackie as they confided and grew closer.
After Lilly's passing, as Sam struggled to recover from one of the lowest points in his life, new challenges emerged. Now, he found himself in need of financial help with mounting bills and college tuition.
Despite this, he was too proud and stubborn to ask his grandmother, aware that it would strain her resources. Sam had also reduced his hours at the restaurant, enabling him to spend more time at home and handle family matters in the wake of his mother's death.
During this period, Sam’s grandmother suggested donating his mom’s things to Goodwill. However, Sam insisted on boxing them up, wanting to keep some items as reminders. The practical side of him reasoned that his grandmother struggled with the stairs leading up to the garage. At the same time, he knew he wanted to protect his privacy—he didn't want her coming across photos or the lingerie Lilly had modeled.
As Sam returned to the apartment, he thought about the times when he and Lilly shared their love and passion for each other over the past year. Lilly would model, take photos, and, most importantly, cuddle in bed together.
That evening, Sam boxed up his mom’s conservative work clothes. Sorting through the closet, he found numerous pieces of lingerie and stockings. He also discovered a folder with several memory USB sticks. Sam’s curiosity led him to upload the files to his computer to review their contents. It was copies of all the photos they took together, along with the modeling.
There was a pic of the evening they bathed together. Lilly had helped him shave his legs and put on some stockings with a garter belt. Sam had a female cosplay event, and Lilly wanted him to win first place. They were both in the bath, wearing wet and soapy stockings. It was a real turn-on. Sam was getting hard just looking at these pictures. That was the beginning of Sam's secret fantasy as a cross-dresser. These definitely had to be secured in a protected file.
There were many photos of the wonderful getaway vacation to Florida. These videos and pictures were of Sam and Lilly together. Sam wanted to make sure these were locked up so that only he could view them.
The next memory stick Sam opened had pictures of Lilly and Jackie holding hands, posing topless in lace fishnet stockings. Both had thong panties. Jackie’s breasts were amazingly large and perfectly formed for her age. Lilly never revealed that she had another female friend/companion to share her fantasy. Sam quickly uploaded all the photos to his backup drive and had it locked with a security code.
Sam’s cell phone rang, and he glanced at the screen. It was Jackie calling. “Hello, Jackie,” Sam said, as he now envisioned her half-naked while chatting on the phone.
“Sam, I’m so glad you’re home. If you need someone to talk to, Sam, please feel free to come over or call me please.”
Sam thought to himself as he envisioned Jackie almost naked in the photos. She was the opposite of Lilly; her skin was tanned and smooth, and her feet had a tan line where the tops and bottoms met. Sam would often daydream about taking photographs with her, and now he desired her more than ever after learning of the secret she had shared with Lilly.
“Thanks so much, Jackie.” As he glanced across the street, he could see her in the window of her bedroom as he peered out the front window of the garage apartment. They were about the same level because Jackie’s home was on a hill. Sam waved as he spoke; she waved back.
"Sam, would you mind coming over right now? I could use a man’s help.”
“Absolutely, Jackie, I’ll be right over as soon as I put some things away.”
It was around 10:00 PM on a Friday night; Sam walked across the street, up the driveway, and climbed the stairs to the front door. He could almost see his breath in the cool evening as fall was approaching. Sam was about to knock on the door when all of a sudden, Jackie swung the door open, as Sam’s knuckles rapped on air.
“Sam, please come in, hon.” Jackie had the habit of calling everyone hon when she addressed them.
Jackie embraced Sam and hugged him gently as he entered the home. Jackie wore a pink knit long-sleeved sweater, leggings, and pink fuzzy bedroom slippers that showed off her beautiful feet and painted toenails.
Sam started the conversation: “Wow, it’s chilly in here. Do you have your heat on?”
“The furnace is not working. I called for service, and they will be here tomorrow. These homes are now going on 30 years old, and things are wearing out. Sam, I was trying to get the fireplace going. Could you help? I think the flu is closed, I can’t seem to open it.”
“Sure, let me feel around for the handle. Do you have a flashlight?”
"I’ll get one from the kitchen. Would you like some coffee, Sam? I'm making a pot," Jackie said, heading to the kitchen. Sam watched her walk away, noticing her confident stride.
"Here you go," she said, handing him the flashlight as she bent down.
"Here is the lever; it is stuck a bit." Sam reached for the lever, pushed it forcefully to open the flu door, and then pulled his soot-covered hands back, noticing a cut on his knuckle.
“I’ll get some logs from outside, and let’s get this place warmed up,” Sam exclaimed.
“Sam, there is kindling wood in the garage and the pile of wood I just had delivered out back. I’ll get some work clothes on and help you.”
“Don’t be silly, I’ll get this done in a flash, Jackie,” as Sam put his coat on and exited the back door.
Sam grabbed two armfuls of split wood and piled them by the fireplace, while Jackie prepared snacks and coffee in the kitchen.
“Do you have matches or a lighter?” Sam asked as he was putting kindling and logs in the fireplace.
Jackie returned from the kitchen with some paper. "I have a butane lighter on the mantel, here you go," she said, reaching up for it and brushing past Sam.
“Um, Thanks,” as he lit the fire and made sure the draft of smoke was going up the chimney.
“Sam, you cut your hand.” Let me get some wet cloths and a bandage for your hand.”
Sam continued adding split logs to the fireplace, creating a roaring blaze. By the time Jackie returned with pillows and a bandage for his hand, the fire was well started.
“Here, let me wash your hands and bandage that cut,” as she plopped the oversized pillows down beside the fire. Sam held her hand as she kneeled down to get comfortable. “Sam, I am impressed by your maturity for a young man in his twenties.”
“Thanks, I'm sort of modest when people keep telling me that.” Sam chatted back.
"Sam, it's true, your Mom told me when you were growing up, your father was hardly around, traveling the world, and you only had your grandfather when you moved back here."
Jackie washed and bandaged the cut, then kissed his hand and said, “There, does it feel better?” Sam thought to himself, if only she knew how much better.
Sam took a sip of coffee as Jackie had removed her fuzzy slippers and held her feet closer to the fire. Sam’s thoughts made him wonder if she was trying to be romantic or if it was her personality. How would he open a conversation without offending her?
"Sam, I really miss the times we went to our cosplay events together," she said, playfully teasing his leg with one finger.
Sam noticed her curled up beside him, wearing knitted leggings that revealed her bare legs from mid-calf, and a matching knitted sweater that barely covered her panties. The outfit was one she and Lilly had bought together, and he couldn't help but wonder how she knew it was a hidden fantasy of his.
“Jackie, for several years now, each time you have come over or we all three went to cosplay events, you have attracted me, and I was always too shy because of our age difference to mention it.”
“How old do you think I am, Sam?”
“I didn’t mean it that way, I just viewed you as close friends with my Mom, and until now, I was too shy to tell you. Besides, you are one of the sexiest women I know. You have an alluring quality about you, so much more than girls my age.”
“Sam, that is one of the best compliments I’ve had,” as she moved closer and warmed her feet by the fire. “Sam, could I admit something to you?” Just at that exact moment, Jackie’s work cell rang, interrupting the moment.
“Give me a moment, Sam, my boss is calling.”
From the conversation, Sam could tell her mood had shifted from romance mode to work mode.
Jackie answered, “OK, Mr.C, I’ll call the IT guy and see if he can fix it.” As she hung up, she quickly called the IT person, but his voicemail said he was out of town until Monday.
“Sam, I need to get our computer system rebooted. Mr. Carlson is traveling and needs to retrieve some information, and our system is down.”
“Don’t panic, maybe I can help. I have 2 years of experience in IT security and am ISCM-certified. Do you have your work laptop handy? I can fix your system if you have the passwords.”
“I have the information stored, but Sam, I could lose my job if the boss knew I breached security.”
“Trust me, Jackie, I can work remotely, and as you said, most of the time all it takes is to reboot your server.”
Sam took the codes and password, started typing into the system, performed some maintenance tasks, then rebooted the system. Within 30 minutes, the company network was up and running. Jackie called her boss and said the network was fixed.
“OMG, Sam, you saved my life,” as Jackie gave Sam a wonderful hug of appreciation. “Sam, I owe you a favor.”
Sam mumbled, “You might put a word in for me. I need a job.”
“What do you mean, Sam?”
Sam explained his dilemma to her: he needed money to pay his tuition, and his part-time job at a restaurant wouldn’t cover the bills. He would have to drop out of college for the next semester. The glass business had to be sold because his grandmother was unable to manage it.
“Jackie, I feel bad enough not paying my grandmother rent.”
“Sam, meet me here on Monday morning, and we will get you started with a job at the construction company. I’ll call Mr. C and arrange an interview.”
Sam embraced her, "Wow, Jackie, you are a lifesaver if this pans out.” With that, Sam headed back across the street to the apartment. Jackie seemed to be disappointed. Maybe it was for the best. Her attraction to him, maybe, was pent-up lust, and she didn’t want to risk losing her best friend's son.
The next morning, feeling curious after looking through all the pictures, Sam decided to sort through the stockings and lingerie, still neatly stacked in their original packages. He came across a pair of black lace stockings, then hopped in the shower, lathered up, and shaved. Sam had kept his legs and body smooth for years, and after showering, he applied lotion before carefully pulling on the stockings and fastening a garter. Dressing this way gave him a quiet pleasure he couldn’t quite explain, and he often spent hours modeling and photographing himself in such outfits.
As he admired his look, his thoughts drifted to Jackie, wondering if he should have stayed. Determined to help her stack and split wood, he pulled on a flannel shirt and jeans, then headed over. When Jackie opened the door, the sight of her sent a rush of excitement through him, like the drop of a roller coaster.
“Well, what brings you here on a Saturday morning?” Jackie said coyly.
"Let’s get that wood split and stacked, Sam remarked. And besides, I ran out of here last night too quickly. Here I brought you some cinnamon buns my grandmother baked.”
Jackie had put on a pot of coffee and started explaining, "You didn’t have to do this. The HVAC guy is on the way over to fix the furnace, and the wood you split last night lasted overnight, keeping me warm."
Sam thought, “I could have stayed and kept you warm,” but he was too shy to say it aloud.
In just a few hours, he split all the wood, stacked it neatly, and cleaned the back porch. Later, over coffee and buns, they made small talk, both aware of their mutual attraction but avoiding the unspoken tension between them.
For the rest of the weekend, Sam often wore sexy outfits. most too small, though the stockings fit perfectly. and filmed himself in them. Eventually, he packed the clothes for Goodwill, keeping the more risqué pieces locked away.
Sam brought the Goodwill clothing to his grandmother and mentioned that Jackie really appreciated the cinnamon buns. He told her about the job opportunity and how he’d helped with her fireplace and chopping wood. His grandmother thanked him, saying she planned to take the clothing to the church with some friends who were coming over to visit.
Monday morning, Sam was over at Jackie’s home early. She answered the door. She was dressed to the 10’s and had heels and stockings for work. She had a forest green silk top, a short black skirt, and as she walked in her sexy way, he could see the outline of her dark stockings where the hem of her skirt exposed her thigh.
“Well, come on in, Sam.” What’s the matter, cat got your tongue? “
"No, it’s uh... (stuttering), you look especially attractive this morning.”
Jackie said, “Sam, you never answered me Friday night. How old do you think I am?”
“Jackie, you remind me of my mother. I’d say you look to be in your late twenties. Any man would be lucky to have someone like you.”
“Sam, you are a charmer. Lilly and I were close friends, and she helped me through some difficult times. I was going to tell you the other night about our friendship, but you rushed out of here before I could explain."
Jackie sat there, legs crossed, skirt hiked up so you could barely see the tops of her stockings, and she kept shaking her leg with one of her heels dangling by the toes. Sam was afraid his arousal would show, and that would be embarrassing.
They cleaned the dishes and left for work. Sam tried to focus, not looking at her legs, but noticed she was driving barefoot.
Jackie couldn’t help but notice, she said, “I always drive like this. Driving with heels is difficult.”
Sam said, “I guess so, I never tried it”. They both chuckled as the drive was not that long. They arrived at the office about 15 minutes before start time. Jackie checked her messages, and one was from her boss, saying he had to go to Minneapolis and would be gone all day.
Jackie said, “Well, let’s get as much paperwork out of the way. I’ll put a good word in for you. He already knows that you are the son of Lilly.” Sam looked around her office, and there on a bookshelf was a picture of Sam and Lilly at dinner, one of the shots they had taken on the Florida vacation.
“Jackie, where did you get this?”
“Your Mom kept this photo on her desk, she said it was the happiest time of her life. When she took medical leave. She wanted me to have it.”
Sam said to Jackie, “It was a special time for both of us. By all means, please keep it.” Sam had wondered now what the relationship was, but regardless, he was glad his mom had such a close friend. Sam filled out the application and attached a copy of his resume.
Jackie spoke, "Sam, you have 2 years of college in IT. We have openings on the crew. Have you ever thought about being an electrician or a plumber? These guys make great money.”
Sam replied, “I promised Mom I would get my college degree. I have a college loan to pay off, and the little bit of salary I get from waiting on tables doesn’t help that much. I really want to graduate.”
Jackie replied, “I’ll talk to the owner. We will see what we can do, maybe offer you part-time work as IT, and do odd jobs.”
"Jackie, I really appreciate your time, but I wouldn't want you to risk your job going to bat for me."
“Sam, could I say something to you? I can see your Mom raised you correctly, you are independent, and want to work. Most college kids I see want to be the boss, and they are living off their parents.”
Jackie started to explain, “I’m going to leave the office at noon. I need to stop by to get some blueprints for the construction site. We can have lunch on the way home if you like.”
“Sure, that would be nice, thanks, Jackie.” Just at that moment in the conversation, her cell phone rang.
When Jackie hung up, she explained, “That was Mr. Carlson, the boss. I need to drop off some things in Minneapolis for him. Would you mind coming along? I can drop you off afterward.”
They delivered the blueprints to the foreman at the construction site, who handed Jackie the folders Mr. Carlson needed. With about an hour’s drive to the next stop, they swung by a fast-food drive-through for lunch.
Jackie parked the SUV near some trees in a quieter part of the lot. “Mr. Carlson doesn’t like people wearing high heels at construction sites, so I’m going to change in the back seat. Hope you don’t mind,” she said.
“No, of course not,” Sam replied. Jackie took off her heels and asked Sam to unzip her skirt. He obliged as she turned her back to him. She quickly swapped her outfit, trading her skirt and top for khaki shorts, a blue company-logo shirt, and tennis shoes.
As the two ate their lunch in the car, Jackie remarked, “I hope I didn’t shock or embarrass you, but I had to wear work clothes on site, it is company policy.“
“Absolutely not, but I’m sure the day can’t get any better than that.”
Jackie just smiled and placed a hand on his leg, saying thanks. Just her touch on his thigh made him have a hot flash of excitement. As they drove away, Sam started daydreaming of the two and how great it would be to have sex.
They arrived at the site, and Jackie said, “I’ll only be a few minutes.” Jackie walked over to a construction trailer and entered. It took about five to ten minutes, and Jackie came out to the car with a man wearing khaki pants, the same blue shirt, and work boots.
Jackie opened the door and said, “Sam, this is Mr. Carlson.”
Sam got out of the car, shook his hand, and said, “Thanks so much for taking some time to greet me. I know you must be very busy.”
Mr. Carlson, “Sam, your mom was a very important employee to our company. Jackie assures me you have the same work ethic. I tell you what. We currently outsource all our IT work, but I would like you to come on board and manage that for us. That would be part of your job, but I need an assistant from time to time to run these errands. Jackie is too valuable in our corporate office. You will receive a salary of $55k a year, and we can work around your college schedule so you can finish your degree."
"Well, what do you think you want to come on board? And Sam, just call me Mr. C, all the guys on the crews do the same. Well?"
“Mr. C, you have made a deal. I work at a restaurant and would like to give them at least a week’s notice if that’s OK?" Sam remarked.
“Alright, welcome aboard. I will want you to start next Monday morning.” With that, Mr. C said he needed to get back to a meeting.
Jackie and Sam got back into the SUV and started driving home. Jackie remarked in her nice, low voice, “Well, Sam, that made your day better, right?"
Sam replied, "Yes, the second best thing of the day, next to you changing into your work clothes.” They looked at each other and chuckled.

“I forgot to tell you, Sam, your Mom had a company car, and I reminded Mr. C to let you have a car to sweeten the deal. Besides, you will need one to be Mr. C’s right-hand man, running errands.”
“Wow, Jackie, you are amazing. Tell me about that phone call. Did Mr. C want you specifically to deliver those things?"
“Sam, you are very insightful. I wanted you on our office team and took the opportunity to promote you to Mr. C today, not sometime later; he gets too busy and forgets.”
“Jackie, thanks so much, I don’t know how to ever repay you, and I'm curious about one other thing."
”What’s that?" Jackie remarks.
“Is there a company policy about dating other employees?" Jackie just smiled; she knew where Sam was going with the conversation.
“Tell you what, Sam. Your Mom always talked, no bragged about how she was anxious to get home and have a foot massage. If you could come over after work and give me a foot massage, that would be plenty."
Sam exclaimed, “She did tell me she told all the gals. I thought she was exaggerating.”
“Sam, that’s one of the most caring things to share. You should be proud of yourself, not embarrassed. I would like you to do me a favor now and give me one of those foot massages.” Jackie said in her coy way of begging.
“OK. Agreed, because you have been my savior today, and I owe you a lot more than one. Just one more thing, Jackie, let’s keep this our secret so the other girls do not want the same treatment.” They both laughed. But Sam was inwardly excited to know they shared a passion, remembering the photo he had seen of Lilly and Jackie together.
They arrived back home around 6:00 pm and went into Jackie’s home. She kicked off her tennis shoes, took off her clothes, and headed into the bedroom. Jackie returned and asked if he would share a glass of wine with her. Sam was 22 now, and wine was perfect. He never got into drinking like other college kids; besides, he worked nights and went to school. Sam was not a party animal. He thought to himself. Lilly had given him inspiration, and maturity had given him so much more than a typical college life.
Jackie lay down on the sofa, still wearing the nylons and kaki shorts. They sipped the refreshing wine and toasted to a new beginning. There was a moment of silence, so to break the ice, Sam said to her,” Lie back, rest, and put your feet on my lap.” As she did, Sam started massaging her toes, then the sides of her ankles. Jackie was purring like a kitten. Sam suggested a skin cream to make her feet look like she had been to a salon.
Jackie said, “Let me wash my feet first.” She removed her stockings, ran some water in the sink, washed her feet with a soapy cloth, and rinsed them off in the shower. Before Jackie resumed her place on the sofa, they poured two more glasses of wine, and Jackie unbuttoned her shirt to stay cool. Unlike the weekend, it was in the mid-seventies, and the house needed a breeze. Most older homes in Minnesota did not have central air.
As Sam applied skin cream to his hands, he resumed the foot massage. “OMG, Sam, that’s wonderful,” exclaimed Jackie.
Sam wanted to give her the full treatment in appreciation for going to bat for me with Mr.C. As he pressed his thumbs into the small of her feet, rolling his fingers over the tops, pinching and stretching her toes, she was again purring like a kitten. Sam, again being aroused, had an enormous hard-on, and Jackie kept brushing her foot across it, making him aroused and his mental state on edge. Sam looked up, and she was tracing the upper edge of her bra with her fingers, then running a finger down her cleavage to wipe away a bead of sweat. Jackie picked up a magazine off the table and tried to fan herself.
Jackie jumped up, said, “This is ridiculous,” and took off the blue company shirt. Sam just stared at the most perfect breast, the material was a light pink lace pattern that you could make out her nipples.
Sam said, “You look fantastic. Does that come with matching panties?
Jackie said, “It does, but you can’t see them right now."
She lay down, Sam continued the massage, and did her nails in pink as well. Sam carefully did the tips in white. Jackie again was teasing Sam's arousal, and Sam, being the gentleman he was trained to be, acted like it did not faze him, but Jackie knew to herself he was on the brink of being passionate.
“There you go, French nails for a beautiful person,” Sam said, well, it’s getting late, I want to make sure my grandmother knows I’m home, and let her know I got the job."
Jackie said, “I was hoping you would stay for some dinner.”
Sam said, “Could I have a rain check?” He wanted to stay, yet remembered the words Lilly had told him not to be too anxious.
“Absolutely,” Jackie said in somewhat of a disappointing manner.
Sam walked to the door. She went with him with a hand on his arm. As they reached the door, her hand slid down to his hand. They had an awkward moment there. Should he kiss her, shake her hand? Sam leaned in to kiss her on the cheek, and she turned, and their lips came together for a soft kiss.
"Good Night Jackie…"
"Good night, Sam," And instinctively they kissed again. This time it lingered.
Walking back home, Sam kept thinking she had sent mixed signals, confusing him about where their relationship was headed. He hoped she didn’t notice his pants were stained with pre-cum. Upon arriving home, Sam explained the good news to his grandmother. He also said he would pay her $ 1,000 a month and cover the utilities as long as he was employed. She said he did not have to do that, but knew she was as excited to get the help as he was.
Sam didn’t eat dinner that night, but showered and put on a pair of the black satin boxers Lilly had bought for him. He sat down and started looking at a slide show of Lilly and Sam.
He had all the lights turned off as he walked past the front window. He looked over at Jackie’s house, and there was a light at the bedroom window. He could, once in a while, see her silhouette pass by. Sam thought it odd that he had never looked before, since there was a clear, straight view of her bedroom.
Sam had a box of wine in the fridge, so he poured himself a glass and added some ice cubes. From that moment on, whenever he walked past the front picture window, he found himself lingering to see if he could catch a glimpse of her. Was this just a casual interest, or was he becoming obsessed with her?
It was Wednesday as Sam’s phone rang. It was Jackie, as he answered, “Hello, stranger.”
“Sam, I figured you would call me before now. Anyway, Sam, I am taking the day off Friday, how about that raincheck either Thursday night or Friday?“
"Jackie, I know I should have called, but I hesitated several times."
“So you were thinking of me, huh?
“Yes, Jackie, I can’t get you out of my mind. How about dinner Thursday night after work? I’ll give you a massage you only dreamed of.”
"Oooh, Jackie cooed. It’s a date on Thursday at 6:00 PM."
As Thursday afternoon came around, Sam called Jackie’s cell and said, “Hi Jackie, I was thinking I would get Chinese take-out for tonight so you would not have to cook.”
Jackie replied, “How thoughtful, thanks, but I was going to ask you to cancel, my company car is in the shop until tomorrow afternoon. I was going to call Uber to bring me home.”
“Don’t be ridiculous, I’ll pick you up. I’ve been driving my grandparents’ car."
“Sam, I wanted to stop at the mall first. Is that OK?"
“Absolutely, I am all yours for the afternoon.” Sam hung up the phone with a newfound excitement.
The next day, Sam arrived at the office around 4:30 PM and went inside to find Jackie finalizing a few things. The weather had turned cold again, so they both had on coats. When Jackie was ready, Sam wanted to impress her and hold the door for her, and again opened the door to the car for her. As he shut the door, he noticed her nylon tops and just a hint of her bare thigh exposed. He went around and opened the driver’s door.
Jackie exclaimed, “You are impressive, Sam, you have been raised a gentleman. BTW, Sam, my car is in the shop being detailed and serviced, and it will be yours. It’s only 2 years old. Mr. C thought I deserved a new car, so that’s what we do with newer employees.”
“Wow,” Sam exclaimed. "I'll be forever in your debt. I've been thinking of buying you something special to show my appreciation."
"Oh, don't worry too much about that, hon, I know of a special gift I would like from you."
The teasing talk continued back and forth, and they both knew the end of the story.
Jackie explained, “This coming Saturday morning, we need to go to the Mercedes dealership and pick up both cars. Mr. C asked if I could do this for him, as he will be out of town.” The dealership will pick us up at my house.”
They arrived at the Mall in Bloomington, and Jackie directed him where to park so they did not have to walk as far. Sam parked and came around to her side of the car. She started opening the door. Sam grabbed the handle, opened the door, and offered her a hand to help her out. As she swung her leg, her dress exposed her crotch, and his heart raced. Sam wondered if women do that by accident or just to arouse us.
Jackie exclaimed, “Sam, when filling out all the paperwork on you, I noticed you have a birthday next week. Twenty-three years old."
"Yes, I almost forgot."
Sam actually started remembering Lilly, for she always made an effort to surprise him on his birthday.
As the two walked into the mall, the first shop they passed was Aerie, and Sam lingered by the display, admiring the mannequins in sexy lingerie. His thoughts drifted to the time Sam and his mother went to Aerie during their trip to Florida. Sam could not help it as tears flooded his eyes. Sam wiped a tear from his face and hoped that the reality moment would not interfere with the evening.
"Sam, is something wrong?"
"No, Jackie, I was just remembering my mother, as she loved to shop here."
Jackie said, “I understand," as she slid her arm around his to console him. "I want to go over here to H&M first; we’ll stop by there on the way back.”
As they went into H&M, Sam hesitated, but Jackie said, “Please come in with me.”
She tried on several sexy outfits and bodysuits. They do not allow cells or cameras in the dressing rooms, and only one person, because there had been some inappropriate behavior in the past. Each time, Jackie would stand in the hallway to give Sam a view. Still, he was enjoying this as much as she. Jackie had purchased several bags of lingerie. The shopping had Sam dreaming of her and how he could capture each seductive pose. Sam's thoughts of his mother passed and were now secondary to wanting to seduce Jackie.
Back at the car, Sam remembered again to open her door. The rule Lilly had instilled in him about being chivalrous towards a lady showed respect for her.
As they drove away from the mall, Sam asked her if she wanted take-out or to eat at a Chinese restaurant.
Jackie suggested this Vietnamese restaurant on the way home, and since it was getting colder, hot Pho sounded fantastic. It was only at that time that Sam put two and two together that Jackie happened to be part Vietnamese. Sam completely forgot that when they first met, she mentioned that she was part Asian. Sam always thought Asian girls were so attractive.
Arriving home, Jackie asked Sam, “Let’s have some wine, I ‘ll get the glasses, can you light a fire to take the chill off the room?”
Sam thought to himself, they were picking up where they left off on Monday evening after work.
She had taken off her heels, was curled up by the fireplace, sipping wine, in her fuzzy baby blue short dress. Her nylons were coffee-colored with a pattern at the tops. These were the pull-ups with elastic around the legs. They toasted by clicking glasses and took another sip of the wine.
She had some oversized pillows that Sam arranged so she could lie back while he massaged her feet. First, she slid her hands up each leg, exposing her upper thighs, and removed her stockings. Again, Sam’s hands had her purring like a kitten. Her pink French toenails and the seductive surroundings. Sam had to admit to her that it was a turn-on for him also. Sam was massaging her legs. Every time his hands went farther up her legs, her dress would ride up.
Jackie sat up and asked Sam, “I feel we have so much in common, and before we go farther I want to be very open and honest with you. I am unlike most girls; I have something extra to offer.”
This made Sam all the more determined to find out more about her. They stood up; Sam offered his hand to help her stand. Jackie took his hand, and they walked into the bedroom.
“Sam, help me unzip my dress, please? “
Jackie turned around; she did not let the dress fall, but took each of her hands to the sides of his face and kissed him on the lips. Sam placed his hands on hers, and they kissed softly again, two breaths were one as they inhaled and exhaled.
She stepped back, let her dress fall to the floor; now standing in just her panties, bra, and stockings. She handed Sam her camera and asked him to take her picture. As he clicked several shots of her, she then reached in the back, unclasped her bra, and, with her back to him, threw it over on the bed. Jackie had a rose tattoo on the back of one shoulder, as Sam clicked the camera, taking a few shots of it.
She raised her hands to the back of her head, lifting her hair, “Keep shooting, Sam, while I pose for you.”
Jackie also had bow tattoos on the backs of her legs and her upper thigh. This too aroused him, as he snapped several photos of her.
“Jackie, I wanted you to know, I saw the photos of you and Lilly posing together. It was amazing and very arousing."
“ Yes, Sam, we posed together for your Mom to love herself and gain confidence. We were friends, and she would come over here and talk for hours. We posed in front of my camera and a tripod only. Your Mom and I shared our lives with each other."
“Sam, your father would rape her and force her to do sexual things that were disgusting to her. I talked your mother into leaving him and coming back here instead of going to Germany with him. Sam, her self-confidence was destroyed; she had love and sex mixed up. She married too young."
"Jackie, you don't have to explain. Lilly told me some of the sad stories."
"Sam, two people can share love as well as make love, as long as it is respectful, it can be beautiful. Your father did not love your Mom as we do.”
Sam was shocked to hear all this and did not get mad, but just then said, “Jackie, thank you for showing my mom. Did she tell you anything else about the two of us?
Jackie said. “Sam, what your Mom told me was an amazing experience the two of you shared. I vowed never to tell anyone. She loved you as a person, and I can hardly blame her."
Sam hugged her, and a tear fell onto her shoulder.
“Sam, you are a very caring person.” “I also want to show you something else.
As they walked into the other room, an office, Jackie opened her laptop and started a slideshow. The photos were shots she had taken from her window looking into the apartment. They were of Lilly and Sam together, some of Sam with stockings and nothing else. One was just the other day. Sam was stunned; he didn’t know whether to be mad or embarrassed.
“Sam, your Mom knew I was taking movies of you and confided in me. We would watch these together, and we promised to never reveal this to anyone. I was so envious of her, for I myself started to fall in love with you.”
Being a little embarrassed, Sam said, "I can't be mad, but I'm more ashamed, because I became obsessed with the camera as it captured a moment that will never be replaced."
“Sam, it is natural for a man to feel sexy in women’s attire. Many men do this and keep it a secret. As far as obsession, it is more of a passion to display love and the natural, alluring moments."
“Jackie, you wouldn’t understand how a woman finds out you may be gay? You are a woman yourself, how could you relate?”
“Sam. I am transgender.“
“What ?... No way! You're the most feminine person in my life right now." Sam exclaimed.
He didn’t exactly know how, but he did know she was beautiful, and his attraction was real.
“I was born with male genitals. All my life, I was made fun of, and the fact that I have male genitals made it hard for me to love myself for who I am, not what I am. Your Mom and I gave each other confidence. Sam, you have the same fetish, the same desire to love someone. Your feminine side takes over."
“Jackie, you do not know how weird I feel right now.”
"Sam, do you think I am feminine? Or masculine?"
“Feminine, of course.”
"Sam, it does not matter what the genitalia is. If you want to please the person, it is the attraction and caring about them, not anything else."
Sam said, “You know Lilly said the same thing.”
“Here, Sam, look at these.” Jackie had pictures of her with stockings, lingerie, and rear views she had taken for herself.”
Sam was again getting rock hard looking at these.
“Sam, I have never told anyone about this. Please let this be our secret. Sam, your mother, and I ran into the same men who treated us roughly and thought that we were what they saw in porn videos.”
Jackie came up to Sam and whispered, “Don’t you find me attractive? I know you are a good, loving person.”
Sam said, "Yes, but how?"
“The same as you would to a woman.”
Jackie undid Sam’s belt and dropped his slacks to the floor. Sam’s hard cock was pushing out of his boxers. She knelt and untied his shoes, then took them off.
“Sam, step out of your slacks. It’s your turn for a foot massage. You can remove your shirt as well.”
Sam lay on the bed as she took off his socks, applied lotion to her hands, and began massaging his feet.
Wow, it did feel wonderful. Jackie massaged his feet and legs for at least 10 minutes.
She said, “Stand up now”, still in his boxers. “Take the camera and continue taking pics of me.”
Jackie was topless. She asked Sam, “Please kiss my nipples, they want attention.”
Sam complied. The fact that she gave Sam a foot massage broke down all his apprehensions.
Jackie started posing as Sam continued taking photos. She playfully started teasing by removing her panties and then slid them down and off, only wearing stockings. She lay face down on the bed and started sitting up on her hands and knees; this was so erotic that his hard-on was sticking out of his shorts. Jackie took her hands and spread her cheeks apart, exposing a clean-shaven ass.
“Keep taking photos, Sam,”… Jackie started to pull on her small cock with one of her hands. She was not very large, but Sam was so turned on by this that he thought he would burst.
Jackie turned and said, “I see you’re enjoying our evening.”
She sat up on the edge of the bed and pulled Sam’s boxers down to the floor, and upon raising back up, she licked the bottom of his hard cock. Teasing, kissing, and finally slipping the head into her mouth. She sucked and made a popping sound as the head popped in and out, then she slid down on it until it hit the back of her throat. Her other hand started massaging his testicles, and the feeling was almost putting him to the brink.
As Jackie stood again, they kissed with more passion, and as their tongues touched, the thought crossed their minds that Lilly and Sam shared oral sex and kissed.
Jackie said, “Sam, make love to me. Please.” It was in a soft breath of a voice.
Jackie grabbed some lubricant and spread it on his cock. She lay back on the pillows and pulled him on top of her. Their bodies rubbed together, the sight of her nakedness, her large breasts swaying as they moved. She took her legs, wrapped them around his waist, grabbed his cock with one hand, and guided it into her opening. Her breathing started to quicken.
Sam started pumping slowly, as before with Lilly, and the deeper he went, the more she gasped. Sam kissed her on the lips again. They both gasped as their breath hastened as they moved together even faster. Sam was up on his hands now as deep as he could go, and with every stroke into her, she gasped. She started stroking herself as he was getting the feeling he was about to explode into her.
Jackie started screaming, “I’m Cumming Sam”, as her cock spurted several streams of cum between them.
The sight of this made Sam move closer to a climax as Jackie said, “cum in me, Sam cum in me.”
Sam cut loose and as he strained forward into her as deeply as he could, one thrust and he had unloaded his cum as his manhood throbbed with each spurt inside her.
As they both collapsed on each other, she was right. Sam forgot her gender, and it was like making love to a woman. Both their hearts were racing, and they kissed again.
As they hugged each other, she whispered in his ear, “Thank you, Sam, I’ve been wanting that from you all week.”
As she spoke the words, Sam's hand found her cock, and he began to massage and bring her to arousal again. He wanted to please her more as he bent down and started kissing her girl-cock and slipped the head into his mouth. Her moans confirmed the pleasure he was giving her, and his thoughts were to please her as if someone was pleasing him. Sam licked the underside of her cock down to her testicles and tongued the area between her anal button and her scrotum, for that's the sensitive area that he enjoyed.
Sam wrapped one hand around her as he plunged her cock into his mouth and began sucking and stroking her. He could taste the precum in his mouth, and it was not all that bad.
Jackie yelled, "Sam, I'm about to cum" ! as he ignored the warning, he felt the warm liquid spurt into his mouth. It streamed down her cock from his lips as he kept stroking her.
Jackie put her hands on his face and lifted him to her and kissed him again and again, as the remaining liquid strung between their parting lips.
They showered together, washed each other, and played in the shower as two kids. It was past midnight already, and they were washing all the bed sheets. They even made up the bed, but decided the next time they made love, they would do it in the shower.
“Sam, do you mean there will be a next time?"
They actually both laughed at that one. Sam muttered, "You can’t decide when and where. All that matters is with and who."
The next few months were like a honeymoon; they would please each other orally and traditionally. They lie together every night after work and give each other a foot massage.
Jackie, Sam, and his Grandmother decided to celebrate Thanksgiving together. The company no longer needed to outsource the IT work. Sam made sure he completed all software and hardware upgrades and coordinated system security.
Sam started back to school in the spring, taking 8 credits per semester part-time until he got his degree.
It was getting colder this fall. The crew had lots of concrete blocks to lay and was shorthanded, so Sam volunteered to work weekends to help the foreman.
The experience he was getting was invaluable.
Jackie and Sam decided they can afford to gut and upgrade her home one room at a time; she will live with Sam above the garage.
One evening, cuddling together, Sam asked, "Jackie, I never thought I would feel this way again."
"I was dreaming of this moment right here, and I never believed it would happen either," Jackie admitted.
The day after Thanksgiving, they were going through boxes to set up her Christmas tree. Here is a green box with the same angel that his mom had.
Sam said, “Where did you get this?"
Jackie exclaimed, “Your grandfather gave it to me when I convinced your mom to move here. His exact words were, thanks for giving me back my children.”
They embraced and fell to sleep in each other's arms.
The End (or a new beginning.)
