The funeral was officially a thing of the past. That didn't mean that the mourning was over, but Thomas was happy to have the last few weeks done with. The death of his father, Glen, and subsequent events surrounding his sudden illness had exhausted both him and his stepmother. Despite the kindness of friends and neighbors, the preparations for the funeral and memorial had been emotionally and physically draining for both of them.
It also highlighted that nothing in life should be taken for granted. His father had seemingly been in good health until he began having headaches that turned out to be warning signs of an eventual aneurism. When the vein in his brain burst, the emergency surgery was too late, and just like that, his father was gone. Now it was the two of them as a family: Thomas and his relatively new stepmother, Janet. In the course of his youth he had now lost both parents: his mother to cancer and now his father.
Fortunately, money was not an issue. His father, a financial professional, had invested well. Thomas's college fund was enough for even the best schools, and his stepmother was likewise well taken care of. She was younger than his father by almost a decade and still had her good looks. They had been married for seven happy years, and Thomas had grown close to her over time, despite a rocky beginning. The replacement of his birth mother with a relative stranger had been a difficult transition, but Janet had slowly won his heart with her kindness and understanding. It didn't hurt that she was a knockout, even into her early fifties. Thomas had to admit his father had good taste and had found a gem after his first wife finally succumbed to cancer.
Now, though, they were starting a new period of their lives. Thomas was prepping for his second year of college, but he had reservations about it. He was thinking about taking a year off and maybe finding a job and letting things settle. His father would not be happy with that decision, but his stepmother supported him.
"You're old enough to make your own decisions, Thomas. I understand. I would only advise you to think carefully and not make any rash choices. We are both still grieving your dad's loss. It will take some time. Everyone has their way of facing things like this, and if you want some time on your own, I would understand. You're only nineteen and you have a good head on your shoulders. I trust any decision you will make."
As Thomas listened to his stepmother's support, he realized how lucky he was. Janet was open-minded and sensible. It was clear that she and his father were deeply in love, and at no time did she appear to be a gold digger, something that had crossed Thomas's mind when he first met her. In addition to her fantastic good looks, she was an excellent homemaker. The fact that she had a killer body with slim hips and large breasts had initially struck Thomas as a stereotypical bimbo, but she had turned out to be a rock in the eventual marriage to his father. Thomas had not been able to call her mom, but he cared deeply for her, nonetheless.
So, in the days that followed the funeral, they spent much of their time with each other, telling stories about Glen and comforting one another. On several occasions, she had shed tears during their talks, and he would comfort her with his arms around her.
"You've grown to be such a wonderful man, Thomas. You look more like your father every day. You're going to make some lucky woman a great husband...oh, I know...not for a while. You still have many years to prepare for that, but you are so level-headed and handsome. You are mature beyond your years, Honey. I'm happy to have watched you grow into a man."
Thomas did look like a younger version of his father. His dark, good looks were the envy of his friends and the desire of both women his age and older friends of the family. At 6'2" he was lean and fit. He had excelled at several sports, like his father, but despite his good looks, he had always been shy around women. He had dated a few girls but had not had a serious or steady relationship with anyone. That didn't mean there was a shortage of admirers. Studies and athletics seemed to be his focus instead of relationships. And his father and stepmom knew it was only a matter of time before he would get serious with someone.
A couple of weeks after they had buried his father, he noticed travel brochures for warmer climes lying on the counter.
"Thinking about traveling, Janet? I noticed the flyers for tropical locations."
"I was going to mention this to you. I think you and I deserve a vacation to someplace warm, away from snow and sleet that often accompanies our northern spring seasons. What do you think?"
"You don't have to ask twice. That sounds wonderful. Surf and sun! Just where did you want to go?"
So the decision was made. They poured over the brochures and picked a vacation spot on a fairly remote island in the Caribbean. It was expensive, but just what they were looking for: solitude, warm sun, and white beach sand. The bungalows were thatch-roofed and quaint but had all the amenities. The area they chose was limited to only a handful of people at any given time, and the reservation came with kayaks, snorkeling, fishing gear, and crystal-clear water.
"This looks fantastic. The bungalows are well stocked and we only need to submit a list of grocery preferences and everything will be waiting for us. In two weeks we'll be eating fresh fish and drinking mai tais. I can't wait."
"Likewise," Thomas added with a huge grin.
And two weeks later they landed at a small airport in shorts and flowery shirts where a van picked them up and took them to the pier. A large catamaran awaited them and once aboard, they inhaled the warm sea air and enjoyed the hour-long ride to their home for the next three weeks. Their smiles were ear to ear.
The captain of the boat was a local. His dark skin was highlighted by the white uniform he wore. His pearly white teeth were visible in a perpetual smile accompanied by the calypso cadence of his speech and a deep, hearty laugh. As Janet and Thomas relaxed in the back of the boat soaking up the sunshine, he remarked to his first mate about the couple.
"I'm not sure who is in charge, the criss gyal with the large ti tis or the mon with the muscles, but I'd be happy to service her if he's not up to it."
The mate nodded and smiled. The Jamaican slang was not lost on him.
"Ya Brudha. She has big boobies, fer sure. More than a mouthful, eh?"
They both turned and smiled at the couple. Janet's halter top was stuffed with her flesh and Thomas struggled to avoid staring at her chest. His nylon shorts gave credit to his thoughts, however. The bulge between his legs was not lost on his stepmother. The thought of three weeks alone with her created wayward ideas he had trouble dismissing.
Janet's smile belied her own preoccupations. The bulge her stepson was wearing was not lost on her.
I wonder if he's as big as his father? she mused. A dampness formed in her groin. She reached over and kissed him on the cheek.
"I'm so excited. Aren't you, Thomas?"
*****
Soon they were entering a small protected inlet with Bungalows scattered along a stretch of white sandy beach but set back into the jungle growth. Each bungalow had privacy fences on either side even though the bungalows were a good 50 yards apart. The catamaran pulled directly up on the beach and the captain and his mate jumped out into the thigh-deep water as the vessel came to a crunching halt in the soft sand.
"Come around to the bow of the boat, Missus. It is shallow there, and I'll help you."
Janet realized she was going to get wet and removed her shoes. She scooted to the gunnel as the captain stood in front of her with arms out. As she slid off the gunnel, she lost her balance, but he caught her and for a few seconds they were locked in each other's arms before he lost his footing and fell backwards. The water broke his fall and Janet landed on top of him, their bodies pressed together for a few seconds until she could separate herself, but not before she felt a large bulge develop under her.
"Oh, I'm so sorry. That was clumsy of me."
"No worries, Missus. The water is warm. Are you okay?" He shrugged an apology and smiled.
After several reassurances, all were fine. It was only later, after the boat was unloaded, that Janet realized that her nipples were prominently displayed in her wet halter top now clinging to her large breasts. She was thankful she was wearing a bra, something she had considered leaving off due to the heat.
Thomas made no attempt to look away at first. When his stepmother noticed his expression and then realized her large nipples were the cause of it, she automatically covered them with her hands.
"Oh my god. Sorry Thomas. I didn't realize I was putting on a show. You don't want to see an old lady's boobs. I'll change in a minute once we get a bit settled."
"No worries, Janet. It's not like you're naked. Just a bit nipply. Sorry, I couldn't help but stare." Of course, Thomas had seen prominent nipples before, but these were shouting at him. I bet dad had fun sucking on those puppies, he almost said aloud.
Back on the boat, the captain grinned at the mate. "Yes, Mon. They be real enough. Just like my cock." They both giggled at his joke. "We be checking on her all de time."
Meanwhile, Janet and Thomas examined their new home for the next few weeks. It had everything they needed...a refrigerator well stocked with food, beer, and a bottle of white wine. a freezer likewise stocked with food for several days, all the necessary appliances including a washer and dryer. Everything was a bit older but appeared to be in good order. The storage room had extra everything, including alcohol. Janet liked her toddies.
They inspected the rest of the premises and put away their clothes in the two bedrooms. Janet shut her door and then emerged wearing a two-piece swimsuit. While not exactly a thong, it was more revealing than anything Janet had worn in front of her stepson before.
Thomas was similarly attired in a pair of bright red Speedos.
"Ta-da!" My clothes for the next three weeks, unless I decide not to wear any!" She giggled at the thought. "Don't worry, Honey. I won't embarrass you. We're here to relax and have fun. Come here and hug me."
Thomas embraced his stepmother, and she whispered in his ear, "I'm so happy to be here with you. I wish Glen could be here, too, but you're the next best thing. You remind me of your dad so much."
And with that, she squeezed him to her and kissed him, first on the forehead and then on the mouth. Just a peck. But it caught Thomas by surprise. He was unsure how to respond, but instinctively he kissed her back. This kiss lingered just a bit longer and he was aware of her large breasts mashed against his bare chest with only a thin layer of cotton between them.
Grinning, Janet broke apart from her stepson.
"Careful, big boy. Don't get any ideas just because I'm wearing skimpy attire. I am your mother. Okay....stepmother. But I have to admit; it is nice having a handsome stud around to share such a beautiful place. What do you say we go for a swim? Last one in is a rotten egg."
Janet ran out the door with Thomas in hot pursuit. She hit the water and dove in without hesitation, and he was right behind her. There was no cold water shock to worry about...only the blood-warm clear water. that felt wonderful in the heat. Thomas caught her and grabbing her by the shoulders, pushed her underwater. She came up giggling and then did the same to him after first wrapping her legs around his waist. Of course, he could have resisted due to a huge size and strength advantage, but he played along and let her have her way. They frolicked in this way for some time, playfully splashing and grabbing each other until both had had enough and they retreated to lounge chairs.
They were dry in minutes. They lay there soaking up the sun and relaxing in the soft Caribbean breeze.
After a while, Janet looked at Thomas lying next to her and got a started look on her face.
"Oh, Honey! You are already showing a tinge of red. The sunblock must have washed off. I probably look the same way. I'll get some more block so we don't look like the lobsters they call langosta."
Janet ran into the house and came out with a large pump bottle of SPF 50 lotion and after pumping a handful into her palms, began applying it to her stepson's shoulders and back. She worked it in and had him roll over onto his back. Thomas's eyes were closed under his sunglasses, and as she rubbed the lotion over his torso, she couldn't help but steal peeks at the area between his legs. She hadn't had sex in over a month, and like it or not, her stepson was making her horny.
My boy has quite the package. I think he may be even bigger than his father.
Thomas caught her looking but said nothing. When she was done, he offered to do the same for her.
"Ok, but no taking advantage of your old stepmom. Do my back first.
She lay on her stomach, her fleshy breasts flattened to the sides of her torso, and moaned softly as Thomas worked in the lotion.
"Mmmm. that feels so nice. I think I was just starting to burn. We'll have to be careful here. The sun is intense. We don't need to go home looking like we've been radiated."
As Thomas pumped lotion on the back of her thighs, she spread her legs and a whisp of blonde pubic hair peeked out from her bottoms.
"Don't look too closely. I'm at that age where old ladies get cellulite."
"No worries, Janet. Your skin is like a baby's." Thomas worked the lotion around the backs of her thighs and imagined her ass without the bikini bottom. His fingers strayed close to that area a couple of times without eliciting any warnings from his stepmother. She moaned softly.
"You have wonderful hands, Honey. Like your father."
As he worked the lotion in and massaged her calves and even her feet, he felt an uncontrollable erection making its presence. Quickly he walked around to the head of the lounger and massaged the back of her neck. As he started to work that area, Janet reached up and untied her bikini top strings from around her neck. She let the strings flop to the side.
"No peeking at my boobies, Thomas, but I don't want any string marks. I want a proper tan if we're paying all this money."
She rolled over and holding her top to her boobs, smiled. Even flattened, he could see they were huge. Her top only barely covered her nipples.
"I know you've probably seen lots of boobs on younger girls, so I'm not going to scare you with mine, even though I am quite proud of them. But go ahead and rub lotion on the rest of me. Your hands are like magic, Honey. Like your dad's. He gave great massages."
Thomas stood at the head of the lounger and rubbed lotion on the exposed areas not covered by Janet's bikini top. Her eyes were closed and she wore a beautiful smile. He massaged her temples and then her shoulders, daring to extend his fingers to the tops of her boobs. Her breasts jiggled with his motions and he wanted desperately to remove her top but knew better. He imagined her nipples, large pink areolae capped with pencil eraser nubs.
She briefly opened her eyes and realized that her stepson had a huge erection dangling over her face. The urge to reach up with her lips and gently bite it was almost too much. She closed her eyes and momentarily envisioned herself with his cock stuffing her mouth. She imagined it was like Glen's: a fat mushroom-shaped helmet head on the knob-end of a thick shaft, and suddenly she felt a warm tingling between her legs. As Thomas reached over her to put lotion on her stomach, she started to say something and briefly raised her head. As if by accident, her mouth came in contact with a nylon-covered, rigid cock.
"Oops, what have we here? Hello! Nice meeting you!" she giggled. "Oh Honey, you'd better stop. I think you're getting a little too excited. Make that a lot excited. My goodness! I think the snake is trying to escape."
"Oh, shit, Janet. Sorry. Yeah. Sometimes parts of me have a mind of their own. God, this is so embarrassing."
"No worries, Honey. I'm flattered. It's been a while since I've seen a reaction like that. But maybe we'd better go inside and cool down. I can finish with the sunblock. You'd better tend to that thing. I know how men are. Would you like some privacy?"
"No, I'm just going to go and hit the head. You know...the bathroom. I really have to pee. I'll only be a moment. You want a drink or something?"
"Take your time. And, yeah. a glass of wine sounds nice. But I'll get it. Would you like one?"
"Sure. I'll just be a few minutes."
Janet watched as Thomas limped inside the bungalow holding his crotch.
That boy's gonna have blue balls tonight. She giggled, but then she imagined him between her legs as she slowly guided a fat cockhead into her pussy. It had been so long since she had been properly fucked. Thankfully, she had brought something to ease that pain a bit: a well-used dildo. Even at her age, she had needs. She preferred the real thing, of course, The captain of the boat had possibilities, but then so did Thomas.
Janet, you are so nasty. She smiled devilishly.
