Between Amy and Jesse

(Been gone long time, life got in the way but I got hungry to write again and really had fun with this one. Hope you all like.)


Between Amy and Jesse

At seven o'clock in the evening, Amy looked out the window from the guest bedroom of her mother's house. The year-long fight against cancer was lost and she passed the week prior. The storm was due soon and the overcast skies did no favors to her grief. She noticed a shadow outside and leaned closer to the window. A gray SUV sat parked to the right and a strange woman stood in her front lawn gazing at the house. She was tall with long blonde curls, dressed in tight jeans, mid-calf boots, and stylish black trench coat. Her presence was odd and made Amy concerned, especially given the house's relative isolation in the rural part of town. She decided to take a risk and go to the door. Opening it just enough to peak her head out, she asked, “Can I help you, are you lost?” The timid woman apologized for being there.

“Oh no, no...I'm sorry, I didn't mean to scare you, ma'am. I'll be on my way.”

She turned and began walking. Amy stepped out onto the porch and stopped her, still uneasy about what she was doing. “Wait, who are you? Are...you okay?” she asked, this time with more assertion. The woman stopped and turned around with her head down. After a moment of pause, she confessed having grown up there, and lived in the house until her teens.

“I saw that this house is up for sale and I just...wanted to see it again, for some reason. I'm not in the market...I just, felt a need to see it. I'm sorry, I'm leaving.”

“Uh, wait, hold on.” said Amy. She explained the house was her mothers and she listed it for sale while staying there temporarily to pack things and handle the estate. The woman nearly came to tears offering her condolences as the sound of thunder began. Amy invited her inside for coffee. She hesitated to accept. Amy asked her name. She replied “Jesse” Amy insisted she come in while the storm passed. No longer feeling uneasy, she noticed how attractive Jesse was as she stepped onto the porch. She had a curvy figure. Her cheeks were rounded, pleasant features, full lips and soft gray eyes that gave her a wholesome look. Even her voice was intriguing with a silky smooth tone of maturity. Offering to take Jesse's coat revealed her pristine buttoned white top tucked in her jeans. Amy complimented her attire and led her to the kitchen table. “So, you lived here.” she said while loading the coffee machine. Jesse explained it was twenty years ago. At the age of fourteen, she and her younger brother were taken by child protective services due to her mother's alcoholism, who was evicted a year later. Jesse now lived two hours away. Eight months earlier, her mother also passed and she'd been thinking about the house ever since.

Thunder and rain began as the coffee brewed. Amy offered a walk through the house. “It feels weird.” said Jesse, describing how it felt familiar but looked strange being so clean, having different furniture and how it was arranged. “The floor still creaks right here! I used to step over it at night to not wake anyone!” she said as they passed by the door to the side porch. The last room to revisit was her old bedroom, now the guest room Amy was in earlier.

“Wow. Huh, my bed was in the corner, desk over here where you're standing. I used to close the door and listen to loud music when mom was drunk...”

Returning to the table, Amy grabbed two mugs, cream and sugar. “Thanks. Mmm, that smells so good, I love coffee in the evening.” The storm carried on as they shared tearful reminiscence of their mothers, then moved on to brighter topics, laughing together. Their connection was seamless, like old friends reconnecting. They realized their similar age, with Amy one year younger at thirty-three. She talked about her career as a grade-school teacher. Jesse had a practice as a psychotherapist, specialized for trans people. “Oh, are you trans?” asked Amy, immediately apologizing for the rude question before Jesse could answer. She chuckled and confirmed that she was. Amy was stunned at her transition. With the arguable exception of her height at 5'10'' there was nothing indicating any history of masculine features. Her voice, face, hands, shoulders, nothing hinted at how she was born. “You are gorgeous!” Jesse was appreciative and returned compliments, of Amy's slim figure, long brown hair and blue eyes.

They continued their conversation as thunder struck loud enough at times to cause them to recoil, before laughing about it. Amy felt increasing attraction to Jesse the more they talked and was now deeply intrigued by her, including whether she was post-op. She wasn't rude enough to ask but never personally knew a trans woman before and was curious about everything that made Jesse who she was. By the time they realized the weather was calm, they'd spent nearly an hour together and Jesse felt she'd overstayed her welcome, hearing crickets and seeing it was now dark outside.

“Well, the storm is over. I've kept you long enough. I'm...so glad I came here today and met you, this has been great. Thank you for letting me look around. Here, take my number, call me anytime. I mean it.”

After updating their phone contacts, Jesse stood up and asked to use the bathroom. Alone at the table for a minute, Amy felt anxious about letting her leave. Back from relieving herself, Jesse thanked her and headed for the door, putting her stylish trench coat back on. Amy felt the looming absence. She was single and hadn't felt such a connection to anyone in years. Still she feigned being okay with parting ways and walked her out. She stood on the porch after they hugged and watched Jesse walking across the lawn, then was overwhelmed by the need to stop her. “Wait.” she said. Jesse turned around. “You can always stay in your old room if you don't want to drive tonight. I can order a pizza.” Jesse perked up, having hoped Amy would try to keep her around. “Well, are you sure?” she asked. Amy pushed the door open and rested against it, letting her body language answer. She smiled and replied, “I guess I can stick around for a bit.”

Amy offered some wine as they returned to the kitchen table. With their shoes off and glasses in hand, they sat down and continued talking, about Jesse's brother not supporting her transition and them no longer speaking. Eventually they talked about hobbies, travels and interests. When music came up, Amy started Spotify through her Bluetooth speaker. Jesse stood up and invited her to dance. Their moves became more sensual, eventually grinding against each other face to face. When Amy went to turn the speaker down a few minutes later, she felt Jesse's arms on her waist. After enjoying the warm embrace of their bodies touching, she turned around and the kissing began. While twirling their tongues, Amy finally had her answer to a burning question, as she felt something poking into her leg. She became more excited and rubbed her hand over Jesse's bulge. Their kissing intensified as she released Jesse's belt and zipper.

As she knelt and pulled her jeans and underwear down to her ass, what flung outward was a semi-erect penis Amy wasn't ready for. “Oh..fuck” she said while gently touching it and taking in the visual of the most beautiful one she'd ever seen. The skin of the shaft was smooth, with one thick vein along the left side. The head was large and shaped of a mushroom, with a vivid pink color, no curvature, and circumcised. The size was in the sweet spot between exciting and frightening. She wasn't sure how many inches, but knew her ex was about six, and he seemed average at best compared to Jesse. It was imposing enough to make Amy wonder if she could take all of it and still walk the next day. The challenge only aroused her more, despite the uncertainty.

The area was shaved to perfection, as If waxed that day. There was a smell of fragrance with a slight sweaty musk of being tucked all day. Amy found the smell exciting, and the immaculate presentation a welcome surprise. She caressed it with both hands, then pulled her jeans down further to reveal her balls. A large and loose pair hanged low enough to seem burdensome for clothing, but a novelty for sexual encounters. Amy waited no longer and slid her lips around the head. In the past, she gave oral mostly due to feeling obligated, but with Jesse, she wanted to suck it. With one hand on the shaft, she used the other to massage Jesse's scrotum. Her efforts were working. Jesse moaned and couldn't keep a straight face as Amy sucked with vigor and aggression. Saliva dripped from her chin. She stood up and they removed each other's tops, seeing they were a similar size C. Amy licked Jesse's nipples while stroking her erect shaft.

Their hearts raced with arousal as they held hands on the way to her old bedroom, turning on a small table lamp in the corner. With all clothing off, they were in bed. Jesse laid Amy on her back. She kissed down her body, and found herself eating pussy for the first time in years. She was neatly trimmed to a landing strip, and had a sweet, earthly aroma. Jesse was thrilled to return passionate oral pleasure. She usually preferred men, but was bisexual and couldn't remember the last time being into someone so much. Her tongue was precise with the right amount of pressure and softness that few women could resist. With three minutes passed, Amy had her first orgasm. Veins showed in her neck as she gripped the sheets.

Jesse mounted in missionary as Amy was still twitching and penetrated a few inches without a condom. The moment was too intense for either of them to care. She was reminded how good it felt being inside a woman. “Are you okay?” she asked in a gentle tone, knowing her size was often painful for her partners. Amy smiled, confirming she was fine and wanting it deeper. They stared into each other's eyes as Jesse pushed further in, using her length for long slow strokes. Before long, she was getting more assertive. A dominant side of her nature came out that was nothing like the timid person she'd been earlier. She thrust hard and fast. The sound of their hips slapping and bed thumps against the wall became louder. Amy felt stimulation to depths of her vagina never touched before. Vibrant pleasure pulsed through her torso, legs and fingers. Her moans were primal. Her legs were soon shaking as she came hard enough that Jesse had the mercy to pause for a moment after seeing her expression. They laughed and kissed in the reprieve. Barely eight minutes since they entered the room and sweat was already running. They breathed as if having run a fifty-yard sprint. Jesse began again with long strokes. Amy was so wet they could hear it. “You want me to come in your pussy?” Jesse asked in a quiet dominant tone. “Yes, come in me. I want it.” said Amy as her body began to tingle on the way to another climax.

Outside, a young man named Randy arrived to deliver their pizza. A knock on the door yielded no answer. He then noticed thumps, barely audible but enough that he suspected it was the sound of sex. Walking around to the side of the house he noticed light from the window. Amy unknowingly left the curtain open a few inches from when she first saw Jesse. Randy put his face to the window, finding two inches of vision to see their lovemaking. His pulse surged. The room was dimly lit, with only the table lamp's short reach and moonlight through the curtains. The contrast of shadows and illumination gave their bodies a serene appearance. He saw Amy's legs wrapped around Jesse's plump ass on top. He was gripped at the spectacle of her balls swinging back, into the light and then forth into darkness. He nearly dropped the pizza in the excitement. Another minute of their rigorous action and Jesse climaxed. She pushed deeper into Amy and stopped, clenching her ass. They lied still catching their breath. Jesse pulled out, with a pasty mess that slid down Amy's ass to the bedding.

Randy looked on for a while longer as they laid on their sides facing each other. He calmed his arousal and walked over to knock once more. “Just a minute” he heard from inside. Amy opened the door wearing a robe, nipples outlined through the fabric, and skin flushed. After handing her the pizza, Randy returned to the window for another peek, only to find the view inside covered. Jesse noticed the opening in the curtain and closed it while Amy was at the door. With his voyeurism canceled, he got back into his car and headed out, having secured a life-long memory delivering pizzas just before graduating high-school.

Jesse and Amy resumed conversation while eating in bed, still fully naked. They had more wine and were soon having sex again, that time with Amy in the cowgirl position. Having such a well-endowed partner allowed her to bounce freely as high as she wanted, without the annoyance of slipping off. She had another orgasm after five minutes of the most aggressive riding she could recall ever doing. Jesse took her from behind and again, ejaculated inside her. Sweaty, exhausted, full of pizza and wine, they were soon asleep. They awakened around eight o'clock the next morning to sunlight and birds, still embraced in each others arms. “I think my kidneys are sore.” Amy joked.

“Look, you've almost made me have morning wood again, haven't had one of those in years now...”

Jesse was surprised at her semi-erection despite estrogen therapy. Amy asked if she missed them, to which she confirmed not missing them at all. “Ugh...fuck no, you know how hard it is to aim a raging hard dick down to a toilet in the morning?” Following more laughter, Amy asked if Jesse could stay for coffee or if she needed to get back on the road. Grief about her mother now seemed so distant. She wanted nothing more than Jesse to stay but didn't want to seem clingy and understood their time together may have been over. She smiled and replied, “I guess I can stick around for a bit.”