This story is pretty long, so go to the ******** for the start of the romance!
It was a beautiful fall night when the citizens of San Diego’s business community gathered for a fancy gala to raise money for one of the city’s prominent charities. The ballroom was crowded with the power brokers and beautiful people of San Diego, but Ms. Lily only had eyes for one man.
Thomas James Jensen was a tall, handsome man whom people naturally gravitated toward. He was well known for his intelligence and kindness, but it was his warm blue eyes, easy smile, and infectious laugh that people remembered. And on that evening, Lily had decided that he would be her target for the night. Some way, somehow, she would know him better by the time the night ended.
Now for Lily, getting men’s attention had never been a problem. Standing over six feet tall in her Michael Kors heels, her long platinum blonde hair and form-fitting evening gown were the talk of the crowd. Combine that with model good looks and the confident strut of a former track star, and the result was a force of power women couldn’t ignore, and men couldn’t resist.
So getting a few minutes to chat with ‘Tommy’ was not a problem. They knew each other pretty well due to their activities in the local business community, and found they really enjoyed each other’s company as they talked that evening. In fact, Tommy was so enamored with Lily that he asked if she’d like a tour of his 30th floor office suites, to which she readily agreed.
As he was showing her around the office and they enjoyed the majestic view of the city and Pacific Ocean, Lily couldn’t avoid the magnetic pull of Tommy’s presence. She felt comfortable and aroused at the same time. Maybe it was the way he deferred to her and held doors open. Or his broad smile when showing her pictures of his kids. She couldn’t pinpoint it.
So after they finished the tour, it was an easy decision for Lily to accept Tommy’s invitation to join him for dinner the next night. He owned a nice home not far from the city, and wanted to cook for her. Oh, and one other thing, he had a heated indoor/outdoor pool. So if she wanted to bring along a swim suit, an after dinner swim would be an option if she were comfortable.
Later that evening Lily contemplated the situation. She was putting herself in a vulnerable position with a recently divorced man. But she found comfort in the fact that she knew how to handle herself in a tough situation, and from all accounts, Jensen was a true gentleman.
The next day when Lily arrived, she was greeted with a hug and a flute of sparkling wine. She thoroughly enjoyed sitting in Tommy’s kitchen, watching a skilled and creative cook prepare a four course meal (Tommy didn’t know it, but a man who could cook was near the top of the list of Lily’s turn-ons). The thing about him was that he was comfortable with himself, and unlike other men his confidence didn’t wilt in her presence. At times in the past, Lily’s stunning beauty, piercing blue eyes, and direct, flirty personality unnerved men, but with Tommy, it just seemed to increase his warmth and humor. He chopped and stirred, refilled her wine glass, laughed, and softly touched her hand on several occasions, all without thought. She knew right there, she was his for whatever he might have in mind that for evening.
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After a wonderful meal filled with good wine, intelligent conversation, and more laughs than she expected, they adjourned to separate rooms to change in to swim suits. When they emerged, Lily was pleased to see that Tommy still took care of himself. He had the physique of a former athlete, and she was not the least bit dismayed that the years had caused him to get a little thicker. In her opinion, it made it a bit easier for her to accept the negative thoughts she sometimes had about her own body.
As for Lily, she had put on a tasteful white two-piece suit, a bit more conservative than what she usually wore. However, it did nothing to hide her long, toned runner’s legs, flat belly, and just the right amount of sexy cleavage.
After swimming and floating around for a few minutes, Tommy grabbed Lily’s hand and lead her over to the far corner of the pool, where a fountain bubbled and soft music was playing from some hidden speakers. Still the gentleman, Tommy pulled her a bit closer, looked into her eyes, and kissed her. It was definitely not too aggressive, but it conveyed passion and subtle intensity. Lily was very adept at feeling a man’s energy, and Thomas Jensen had it in abundance.
To her delight and frustration, Tommy could play the tension game too, and he stopped at one lingering kiss. He told her he had set out body wash, shampoo, and moisturizer in the guest bathroom suite, so that she could wash the chlorine off her body and hair. Lily was impressed that Tommy had thought ahead that she might want a shower after swimming, and was flattered that he had already known he would want her to stay longer.
After a wonderful hot shower Lily joined Tommy in the family room, where he had made a fire in the gigantic fireplace. After guiding her to a seat on the leather love seat near the fire, he produced a tray of chocolate covered strawberries and a bottle of Maker’s Mark bourbon. After a toast to a new friendship and a couple strawberries, Tommy put his hand on her knee and leaned in for the second kiss of the evening, which Lily gladly accepted. As they were kissing she felt the heat radiating from his body and caught a slight scent of a pleasing after-shave, and she felt safe, and relaxed, and desired. Whereas last night she had set Thomas Jensen in her sights as a target, she had grown increasingly convinced that tonight the roles had reversed. And that caused her to tingle.
What Lily liked was that Tommy was not kissing like he had a finish line to meet. He was gentle and considerate, but still brimming with desire. When his hand went to her breast, and his mouth went to her neck, she was more than willing to help take her shirt and bra off. Now that the clothing was out of the way, Tommy focused all his attention on her boobs, which were just as full and round as they were when she was in college. Tommy was a man who appreciated a woman’s body, and Lily felt that deep in her soul, so she could fully lean in to the pleasure he was providing. He skillfully sucked and pinched each of her nipples, applying just the right amount of pressure to each of her breasts. And as he did this, she felt no hesitancy to let him ease her shorts and underwear off. In the past, she had sometimes been hesitant to offer herself to a man orally on their first night of intimacy, but there would be no hesitation on this night.
After Lily helped Tommy get his clothes off, he returned to where he left off. Starting at her belly button, he kissed his way down over her hip bone to a spot between her hip and pubic mound, which was beautiful, and smooth, and gave her shivers when Tommy kissed there. More than she could ever remember in her life, Lily was aching for her partner’s lips on her pussy, but Tommy wasn’t going there yet. When he passed by he lightly blew warm air over her vulva, but kept going down her leg. As he kissed her inner thigh, he would lightly trace her labia with his index finger, slowly working his finger inward as he kissed her calves and ankles.
When he made his way back up Lily’s leg, it was clear his efforts were having an impact. Every fiber of her being was begging for him to continue, and he eagerly obliged. Finally, finally, he lightly kissed up and down her labia, purposely lingering on each step.
Lily melted from the gentle force Tommy exhibited. His hands were firm on her thighs as he worked magic between her legs. His gentle tongue was stimulating her from top to bottom, and when he teased her clit it was like electricity ran through her body. As he monitored her body language, he gradually inserted two fingers in to her tight vagina and found that special spot that always sent her to the next level. With patience and determination, Tommy shifted his attention to her clitoris, and after a few minutes, worked her into a frenzy that culminated in a leg shaking orgasm.
After Lily came down from her high a bit, Tommy kissed her hungrily, and Lily was well aware of the hard cock nudging her entrance. As much as she wanted him to take her at this very moment, she was grateful for the pleasure that he had just given her and wanted him to experience the same thrill.
With that, Lily sat and and brought Tommy to a standing position between her legs. The whole experience of the moment had pushed her erotic energy through the roof, and she knew for damn sure that she was going to bring Tommy to the same place. She began to brush her lips along his shaft before taking the head into her mouth, and when she heard a soft groan she knew he belonged to her again. With one hand on his hip and one hand massaging his testes, she gave him head with a passion she hadn’t felt in a long time. As she was pleasing him, Tommy remarked that it had been a very long time since anything felt nearly this good, and with a guttural groan, he came in her mouth. While this was not something she normally did the first time, Lily gladly took all that he spilled in to her, and felt that she had just lifted years of sexual frustration from him.
As the waves subsided, Tommy lifted her from the couch into a long embrace, and asked her if she was comfortable with how things were progressing. As she enthusiastically nodded and laughed, their mouths met hungrily, each tasting themselves on the other’s lips. As they were connected this way, he reached under her and lifted her completely in to his arms and carried her to a blanket closer to the fire. It crossed her mind that this nearly 50-year old gentleman had literally swept her off her feet, and in that moment he owned every part of her being.
As they settled on the the blanket, she was overwhelmed by Tommy’s desire and felt like potter’s clay in his hands. They laid side by side for a long time in the fire’s warmth, with Tommy tracing lines up and down her spine as they kissed and giggled. Just as the intensity of their affections began to build, he rolled her on to her stomach and kissed his way down to her bottom.
Here, Tommy found his nirvana. Since her days as a college runner, Lily had known what men thought of her shapely legs and butt. It was a point of pride for her and she worked hard to stay lean and strong. Tommy kissed and squeezed every inch of her, almost greedily, forcefully grabbing and kneading just as she wanted, and just as she needed it to happen, he pushed a finger inside her, eliciting a deep groan. Eventually he moved one of her legs out to open her up a bit, and his finger was replaced with his skilled tongue. The feeling as he pinned her leg down and probed her with his tongue was sending her in to orbit.
At the time that Lily felt she couldn’t get any wetter, Tommy stopped and positioned himself between her legs. But then, she stopped him, and told him she wanted to see his handsome face for this. Quickly, he helped her turn over, got her a pillow to put behind her head, and eased himself into her. Once she fully received him, he relaxed and shifted more of his weight on the her. In this position they were free to kiss again, and Tommy told her this was where he had wanted to be for longer than he could remember.
As with everything else he did, his thrusts were a combination of patience and power. His cock was just the right size, and he seemed to know just the right angles to hit her sweet spots. And he was fully committed to her pleasure, which he proved by moving his hand to a spot where he could massage her clit as he fucked her. They continued this way for several minutes, until they approached a point where Lily sensed a climax.
But not yet! As Tommy was kissing her again, she softly spoke in to his mouth and told him that she wanted to ride him home, and in unison they flipped positions. From here, she was in control, and would be setting the pace for the final stretch. With increasing greed Tommy squeezed and sucked her tits and nipples, as she rode and grinded on his rock hard cock. As he approached his climax, Lily could feel him expand inside her, and that pushed them both to the final orgasm. As Lily collapsed on top of him, they could both feel their juices escape from her body, and they layed together in exhausted ecstasy.
As she remained there with him still inside her, lightly kissing his nose and lips, her hand came to rest on something that had been under the blanket…
Source: reddit.com/r/eroticliterature/comments/dvvrxs/tommy_m_and_lily_f