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The friendship between Tommy and Jillian began simply enough but grew in complexity. A chance encounter waiting in their college bookstore checkout line, evolved over five years when they worked at the same promising software startup in Boston. Despite the evolving nature of their relationship, Tommy remained stuck within the “friend zone” no matter how he tried to negotiate for something more with Jillian.
“I think it’s best for both of us, to keep things as they are right now,” she explained.
In Tommy’s first job out of college he joined a fin-tech, software company as a programmer developing a retail payment processing platform. He became entirely preoccupied with creating new, interesting features and learned how to improve his coding, quickly debugging, getting the algorithms more efficient and becoming an essential part of the team. He prided himself in understanding the real purpose of code and then finding novel ways to optimize it. Jillian was the office manager, a key role in any startup, because she kept the employees fed, caffeinated and the office running smoothly. She was very good at her job. Tommy and Jillian loved the small company atmosphere and excitement of being on their own for the first time.
Boston worked with business to encourage locating in the city, bringing jobs for new graduates, and enticing them to remain, despite the pressure of accelerating rents. This was before covid so the economy was booming and tech companies were plentiful. Jillian and Tommy’s company was still just a core group of employees and everyone knew everyone’s business, so Jillian believed it inappropriate to date Tommy. Tommy thought it just another excuse in a long list of excuses, to not hang out. He was also very mindful that Jillian was transitioning from cute college coed to sexy woman and couldn’t bear the idea of her going off with another guy. She embodied all the qualities Tommy found irresistible. She was 5’6”, slender with subtle curves, very sexy boobs with a seductive shape. She had long black silky hair, always perfectly styled even when it wasn’t and she was always meticulous groomed. She had a habit of looping her long locks behind her left ear with one finger that made Tommy want his own fingers in her long strands. Her face was lovely, mysterious and looked like she kept secrets she wasn’t sharing. Though not a model she cared for herself like one. Tommy life was very simple, efficient software code and Jillian and maybe pizza and beer.
In the previous past five years, Jillian had repeatedly declined Tommy requests for dates. Her favorite excuse was “she wasn’t looking for a boyfriend but she absolutely needed Tommy as a friend.” In fact she said she couldn’t imaging her life without Tommy. What could he say to that? Jillian didn’t have boyfriends, so she wasn’t being disingenuous, even though he knew she slept with other guys occasionally. The software team was mostly smart guys and she could have her pick. They traveled in the same circles, went to the same parties, the same work events, and always ended up hanging out together. He hated the friend zone with a passion but feared being cut out all together would be even worse.
They never discussing jobs after college but coincidentally landed a job offers at the same Fenway startup. The Fenway is a group of neighborhoods in Boston laid out by architect, Frederick Olmsted and made up of brownstone townhouses, brick walk-ups and small apartment buildings. Rent is sky-high in these trendy neighborhood, filled with hip restaurants, newly renovated apartment buildings, numerous companies plus Fenway Park, home of the Red Sox. As a software engineer with a minor in data analytics, Tommy commanded a decent salary and could easily afford a two bedroom. A comfortable Fenway apartment and its proximity to the company made it an irresistible perk. Jillian’s meager income, on the other hand, forced her to live with three young women in Charlestown. It was a 5 mile commute that could take a half hour, considering the typical Boston commute that wasn’t bad. They saw each other daily and being in the same office became closer friends. Jillian frequently went with Tommy after work for dinner. He had a sense Jillian might like him differently than college but he sensed there was still reservations. Tommy waited for any signal that indicated she liked him more than a friend.
As the sun sunk below the horizon on a Friday afternoon, it was common for Tommy to seek out Jillian, to talk about her plans for the weekend. The company’s monthly all-hands meeting had just wrapped up and she was collecting the leftover handouts and beer bottles littering the meeting room. It was just the two of them, and they chatted about the recent meeting and the company’s glowing prospects ahead of their product launch but there was a palpable nervousness to Jillian.
Out of nowhere, she asked Tommy an unusual question. “Why didn’t you try asking me out again after our fatih escort junior year. I don’t understand why?” As the words left her mouth, Tommy’s heart sank and his mind scrambled to understand the reason she was asking this now. “What are you talking about, he thought to himself, “you discouraged me at every turn? You made it very plain.”
Tommy felt like he was being ambushed and took a moment to gather his thoughts before speaking. “I remember you were very clear about not wanting a boyfriend, specifically me,” he replied. “I didn’t want to be a jerk and pressure you. How many times does a guy have to hear, were just friends before he believes it?”
Her next question was again unexpected. “Do you still like me? You know…that way?”
His mind sensed he was being lead into a trap but there was really only one answer to that question. Do I still have feelings for you? Of course I do but if I tell her that, I can’t be sure of her reaction,” he thought.
“I guess,” he said, trying to play it cool.
There was an excitement in her eyes as she pressed him. “So there’s a possibility you still like me. I mean like, like me?”
He smiled at the junior high school phrasing, reminiscent of two kids standing by a locker. “Yeah, there’s a possibility,” he conceded.
He heard a slight sigh before she continued. “Good. Because lately, you’ve been on my mind a lot. Even if you don’t believe it, you’re pretty special to me and we get along perfectly. I’m lucky your in my life.” Her words suggesting interesting possibilities but Tommy kept silent and listened.
“Hypothetically,” she began, her voice quiet, “Would you consider asking me out again?”
I couldn’t believe the question. After all these years being exiled to the friend zone, Jillian was suggesting a change to the relationship.
“Yeah,” I replied, not wanting to sound too eager. “It might be possible. I don’t get it though, what’s different?”
“Good to know,” she said, pushing the last chair into the conference table, deliberately not answering the question. Tommy’s gaze followed Jillian as she left the room, her ass swaying just a bit more than usual.
“See you round, Jillian,” Tommy called after her, definitely perplexed, and with no plans before the long weekend.
Jillian looked over her shoulder, “A girl can change her mind, you know,” she stated. Tommy was flummoxed. Jillian just said, she wanted Tommy to ask her out and escaped without even acknowledging the tectonic shift in the ground they stood on.
“WTF am I supposed to do now,” he thought? He’d leave everything where it was and wait out the weekend. He’d get some pizza and beer and watch some movie. He’d survived five years of chasing Jillian, what was another weekend. Maybe things would look so weird on Tuesday.
Thomas J. Robertson was 22 years old, a data analytics software engineer who was called Tommy all his life. His sisters repeatedly told him he looked like a Tommy, not a Tom. As far back as he could remember, he’d been infatuated with Jillian and despite having other girlfriends, none came close to making him feel the way she did. She’s was smart, funny, and beautiful, all in one amazing package. He felt a pit in the middle of his stomach whenever he looked at her boobs. Jillian looked more like a girl than any girls he’d ever met. She was his first thought when he woke up in the morning and his last before he drift to sleep. The way she looked, the way she smelled and the imaginary sex he had been having with her for five years kept her always just a thought away. He spent more nights than he could count, fantasizing about sex acts with her and all the things he loved about her. Just imagining the smell of her body could make him hard. “Is that fucking weird,” he wondered? Perhaps. But for Tommy, it’s just another reason to want to be with Jillian.
At 6’2″ Tommy was decent looking, with an understated lean muscular build and neatly trimmed brown hair parted on the left side with a well managed beard. His go-to attire was a plain black t-shirt, clean jeans, a quarter zip and any footwear other than sneakers. He loved loafers which were old school or any slip on shoe. His true passion lay in the world of computers, coding and solving complex math problems which endlessly fascinated him. In terms of relationships, he’d several relationships with women but none seem as exciting or dangerous as Jillian. Susan was a previous girlfriend, a Bohemian, who was very confident and spent a lot of time schooling Tommy in just how to please her sexually. She loved lounging around, naked and didn’t mind that he spent hours, obsessed over her body, which were adorned in tattoos. She’d spend Sunday with him, lying on the bed or couch, legs spread offering complete access to her pussy and ass without any desire to cover up. Tommy loved how free she was, that she wanted him to look at her naked body and the delicious çapa escort aroma of her pussy. She’d insist he spend hours, slowly bringing her to orgasms, over and over. Once she made him eat her ass which turned him on because Susan adored feeling his tongue tease her asshole. Once she called him into the bathroom and told him to strip and get in the tub. She climbed on top of him and began french kissing him. She peed a huge stream on his cock.
“I just wanted to see how that felt,” she told him. She was a “one of a kind” highly sexual girl and she didn’t seemed to know or care the effect she had on Tommy but even Susan couldn’t make Tommy forget his desire for Jillian. More than anything Tommy wanted to take all he had learned and use it on Jillian.
Jillian was more than attractive to Tommy; she was everything he could imagine a woman might be, she was the pinnacle of femininity. They had fun together, their chemistry was obvious to any observer. Tommy felt their relationship was always on the verge of becoming but it never quite made it. He obsessed over her body, thinking about every curve and imagining the exploration of her “secret places” even though he had never seen them. Tommy had come to believe Jillian simply didn’t have that spark for him but he definitely had the spark for her. More recently he stopped holding back and began expressing his thoughts to her face, feeling there was nothing to lose. Most of the time she gave him funny looks or said, “You’re bad, Stop it,” just laughing it off. He knew she enjoyed the attention even if she protested.
This weekend, Jillian looked forward to alone time in the apartment. Her two roommates, each planned a visit home, for the long weekend. She came home after work with Chinese food in hand and a bottle of red wine and slipped out of some of her clothes. At 7 pm, Jillian casually walked through the apartment naked, a glass of red wine in hand, lighting candles and waiting for hot water to fill the tub. She loved the complete freedom. Bath oil fragrance slowly drifted through the apartment causing her to relax while the candles created a comforting, warm glow. She teased herself and got in the mood by playing with her right nipple. It felt delightful and her manipulations went straight to her pussy. She was unconcerned with being seen naked in the apartment’s large bay or any other windows as she glided unbothered through the apartment. It actually made her even more excited thinking someone, right now, might be looking at her tits and pussy. She could feel herself getting wet from the thought. She looked with pleasure into the night, wishing some nameless boy with a big cock might be right here, to appreciate her gorgeous body and fuck her silly. Everything was so tense lately at work and she felt the need for several orgasms. Then she thought of Tommy and wished she could have invited him over. He would have gladly done anything she asked for the chance to be with her. She could have made him serve her all night without the slightest obligation to fuck him. She smiled at the idea of Tommy as her naked slave washing her, doing her toenails then orally pleasing her as many times as she wanted. She walked back to the bathroom to check on her bath.
Jillian saw everything ready and she placed the wine glass on the tub’s edge. Slowly she eased several toes in the steamy water, adjusting to the temperature before letting her whole body submerge. The hot water felt amazing as it filled the space between her legs and felt so good on her labia. Her mind remained on thoughts of Tommy and their last conversation. She loved that he found her pretty and enjoyed even more that he lusted after her body in the worst way. She knew he wanted her in the worst way. Her pussy began tingling from the hot water heating up her labia and made her imagine it was the heat from Tommy’s tongue. She really needed to get fucked but it needed to be the right situation. Tommy was going to do it, though he didn’t know that yet, and she would insist he do the one thing she always fantasized about. She took another sip of wine and a wonderful warmth and contentment spread through her insides.
Her boobs floated in the water with just her nipples breaking the surface. Her legs stretched out letting her toes touch the opposite end of the tub. She looked at her buoyant boobs and loved her petite and pretty body. She reached down and spread her ass cheeks allowing the hot water to surround and warm her asshole. Later she would make sure she was completely hairless but now her large inner labia lips and clit felt like they were growing fat from the hot water and thoughts of Tommy. It was the thing she was most looked forward to sharing with him. He knew she had nice tits and ass but her big, stretchy labia lips were going to be a pleasant treat. She circled a finger tip around her left nipple feeling the sensitive flesh react. It was just the second güngören escort time since she had the apartment completely to herself and this time she was going to indulging her masturbatory pleasures. She took a small sip of wine and the rich roundness of the juice coated her tongue. She imagined feeling Tommy’s lips pressing against her receptive mouth. She could feel her own tongue pushing into his mouth. She thought of Tommy sucking both nipples to hardness and the little devils grew in response to her thoughts. She knew she would soon feel the overwhelming desire to have her pussy completely filled. It would be a terrible ache best satisfied with a warm, hard cock. Her eight inch, silicon dildo would have to do.
Her imagination was well practiced in taking her to these sexy place, and there was now very little separating her thoughts from an imagined reality. She really could feel Tommy’s hands on her hips like he was right there squeezing her supple flesh. She knew he was crazy for her and that would be enough to make him do anything she wanted. She felt his hot breath against her neck tempting her with all kinds of naughty things. His hands shook as he caressed between her legs, lingering on the now fat, lips between her legs. She knew her large, hanging lips would be a surprise. How many girls had something so impressive. They were very sensitive and pleasurable and she hoped he would like them. Jillian was self-conscious about that part of her anatomy.
“Bob that fuckin’ asshole.” she thought. Bob Trumble, her short lived high school boyfriend, fumbled with a condom in the back seat of his car while Jillian waited, naked but for her tiny underwear. When he removed them and saw her big labia, laying there he said, “Holy shit, those are fuckin’ big. What are they?” That was the summer between high school and college and her inner lips had a growth spurt, along with her boobs. She loved them for how it made her feel but Bob’s words were very hurtful. Fuckin’ Bob’s words were always lurking in the back of her mind, making her cautious and unsure of men, never wanting to feel like she was some kind of freak, again.
She wanted Tommy to unzip her dress and let it fall to the floor. He’d kiss her collarbone just before trailing his fingers along the goose bumps on her rib cage, releasing the bra clasps so it popped open in the back. He slowly peeled the bra from her boobs and pinching her nipples to erection. Jillian forcefully twisted her own nipples in the water in time with her imagination. Tommy knelt in front of Jillian and slid her panties from her body. Right in front of his face was her full, meaty mass of her fragrant, labia for the first time.
“My god your pussy is unbelievably…gorgeous. It’s so wonderfully…big,” he exclaimed. “I didn’t know it could be like this, I love it.” Every sensation built upon the last in her mind, as he leaned in to gently press his lips to her labia, making everything perfect. Treating them just as she wanted.
“I’ve always wanted you to like them,” she said.
“Thank you for letting me see you,” he said lovingly then quickly licked her very sensitive lips, tasting the moisture he found between them. “I adore your body. You’re perfect.”
She imagined Tommy’s firm hand on her ass, driving his fingers between her cheeks, palming the lobes like a basketball. His other fingers smeared lubricant generously over her wet folds and circled but didn’t touch her clit. Her girly aroma filled Tommy’s head. The tension in Jillian’s belly was overwhelming with the first sensation of an orgasm, then she imagined Tommy inserted two fingers deep into her pussy. “Touch my clit she was begged in her head.” Her body quivered with the imagined thrusting of fingers firmly over her g spot. She wanted, no, wanted him to take her. Jillian’s heart pounded, her breath came in short spurts, on the verge of screaming out Tommy’s name.
She needed this cum. It was beginning to radiate throughout her body. She wanted to let it happen because there would be plenty of time for numbers two and three tonight. She imagined Tommy pressing her body into the bed, trapping her beneath him, unable to move. She adored the idea of being trapped beneath him, buried in the smell of a man’s body, feeling like his penetrating cock was being done to her. Their lips crashing together as he forced open her legs and pressed his fingers into the slick folds. He stretching her labia and pulled them from from her body. She thought they might rip off. Then he released the squishy flesh letting the beautiful folds snap back. He thrusting two fingers inside her cunt pushing firmly towards her stomach. She’d let Tommy to do what ever he wanted because she now was aching for his cock inside her. His fingers, her fingers, they were one in the same, plunged inside her body as far as they could reach. Her pussy was a wet, squishy heaven.
“I love your labia. They’re so fucking, big and delicious. I want to suck them every day,” she imagined him saying, just music to her ears. He determinedly pulled and stretched her labia lips till they hurt but it hurt so good way. Her clit swelled to an unexpected size and demanded it own attention. She pinched it between her fingers and she winced from the exquisite pain and the pleasure.
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