I was married for 16 years and have been divorced for about 3. We just saw our lives in different places. As soon as it was over, I knew I was going to do some things I had always wanted. (More on that later)
I have always been relatively successful-nice house, good neighborhood, few financial worries, good life. But, as I progressed through life, I decided I would live more on my terms. So, the fact that I ride share occasionally usually surprises people. But, it's a way to get out, the people watching is fantastic, and sometimes you even get a great conversation. So, when a notification told me it was getting busy on Valentine's Day, I thought, "Hmmm! Let's go see what this is all about."
I had been giving rides for about 5 hours. It was early in the evening. I had been picking up girls from boys' houses all day. They would kiss him goodbye and pile in with their armloads of balloons, flowers and promises of eternal love. I was totally entertained by the absolute cheesiness of it all.
I had also picked up several single women and delivered them to their girlfriends' houses, swearing off men for the night and heading to the perfect Galentine's Day.
My several hours of travel had landed me in a not so great section of town, but the cheesy Valentine rides were just as prevalent. I rolled up to an older brick home and a young lady got in the back. I really didn't get a good look, but I saw she was carrying an overnight bag. I triggered the app and off we went to the first stop, a shady liquor store. I backed in from across the door and in she went. She appeared from the door in short order, carrying a bottle of "wine" ish. She stepped into the street light. This was the first time I had really seen her. She was wearing blue printed flannel PJ bottoms and a white T shirt, obviously no bra. Yep! There's a story here.
She got back in. People had been saying, happy Valentine's Day," all day. So it was a common topic of conversation.
"Headed to see your Valentine?"
She gave me a drawled out, "Nnnooooo. No Valentine this year. Headed to spend the night with my girls."
It was almost a 30 minute ride to her stop. We joked about Galentine's. We laughed about the cheesy Valentine's rides.
She told me she had graduated college last spring and was about 4 months into her first real job. She told me she had only had one boyfriend in college. She told me it had taken her a while to figure out what she wanted to do, so she was 25 when she graduated. But, she had a legit degree, from a legit university, and was just figuring out how to do life.
She was witty and fun to talk to. Somehow, we got back on the topic of cheesy Valentine's and joked about being single. I joked,"We should just be each other's Valentine. We could be as cheesy as we wanted." We jokingly planned bad balloons, horrible cards, half dead flowers, and a dinner that may or may not be edible.
We were about 10 minutes from her stop. "Would you really do it?"
"Would I do what?"
"Would you really have like a super cheesy Valentine's with someone you don't know?"
I thought about it. I have always been bit of a free spirit and up for an adventure. "No stress? No expectation? No we have to be in love? Just cheese for the sake of cheese? Sounds fun."
"Let's do it! Super cheesy stranger Valentine's Day!" she quipped.
We planned it out on the way to her stop. $25 maximum on cheesy gifts, since I love to cook, I would make dinner. We would watch a cheesy Valentine's movie, and then I would get her back to her friends. She called them and told them the plan. They were expectedly concerned. I told her to turn on her location so they would know where she was. We stopped by and she dropped off the "wine" with a promise to be back in a few hours.
She got back in, this time the front seat.
"There is one thing. You can't make fun of where I live."
"It isn't like you picked me up from a mansion. Why would I make fun?"
"You'll see."
We stopped by a local grocery. We ran in and separated. When we returned to the car separately, about 10 minutes later, I had gotten her a tiny teddy bear holding a rose, and a flowery card declaring completely unrealistic love. She had gotten me a potted succulent and a box of those gross candy hearts with the ridiculous sayings on them. The cheese was in full swing.
About 20 minutes later we pulled up to my gate. I had already learned she could be snarky.
"Oooohhhh. Gated community?"
I chuckled as we pulled into a parking space. Then, she noticed. "You live on a lake?"
"More than you realize."
We began walking down the dock until we arrived at slip #81. I stepped on board.
"Oh my God! You live on a ship?"
I chuckled. "It's not a ship."
"Its bigger than a boat!"
"Technically it's a yacht. A very, very small yacht." And it is. It is only about 43 feet and not anywhere near the size of the big boats at my marina.
I slid the glass door open. She almost shrieked, "It has a living room?!"
"Salon."
What?"
"The living room on a boat is called a salon."
"Sallllooooonnnnn" She mocked me. It would set the tone for the banter for the rest of the evening. "What are you going to cook?"
"Well, since it is cheesy Valentine's it has to be chicken Alfredo. Isn't that what everyone is eating tonight at Olive Garden?"
She giggled. "How are you going to cook anything?"
I pointed down the forward stairs.
"It has a kitchen too?!"
"Galley."
"What?"
"The kitchen on a boat is called a galley."
She, of course mocked me. "Oh. It's a galley. Where is the bathroom?"
"Head."
"Ahead where?"
"Not ahead. The bathroom on a boat is called a head. Through that door to port."
"What's port?"
I acted frustrated. "Lefffft. Left is port."
She shot me a bird and disappeared through the door.
I finished the Alfredo. We sat at the table and ate, and drank way better wine than she gave to her friends. We talked and joked. It was light and fun.
"I can't believe there is a full sized bedroom"
"Stateroom or cabin."
She faked being annoyed. "How do you sleep on that bed? It is full of stuff."
"Berth. And I don't. I have a different one. It's in the back."
"I need to go to the, she emphasized, "Heeeaaddd" again."
"Hit the head."
She flipped me another bird. "HIT the head."
"Do you want a cocktail?"
She turned on her best smart ass. "Is there a different word for cocktail?"
"Yes. Gin and tonic," I said dryly. "Do you want one?"
"Absolutely."
"Great come up to the bridge when you are finished."
"The what?"
"The bridge is the... Nevermind. Climb that ladder when you're done."
A few minutes later her head popped up onto the bridge. When she looked out she froze. I saw the wonder on her face. There were a few lights bobbing in the marina and out on the lake. The moon reflected off the water. It was a view few people will ever know. She clued into it immediately.
I sat with my back to the stern of the boat. She sat, leaned on the sun chaise, facing me. We chatted some more, enjoying the beautiful views. At one point she put her feet up and leaned way back. "What would a Valentine's Day be without a foot massage?" I gladly obliged. We were having an amazing time.
We each had 2 more cocktails taking our total to 3 cocktails each and a split bottle of wine. We weren't drunk, not even really tipsy, but nothing I would take a chance with.
I picked up my phone.
"What are you doing?"
"Calling you a car."
We descended the ladder that led back into the salon.
"Well, I knew you were lying to me, anyway!"
I was taken aback. "Huh?" was all that came out.
"You said we were going to watch a cheesy Valentine's movie, and I haven't seen a single TV on this whole boat!"
At that, I actually laughed out loud. I walked over to the port side credenza and pushed the button on the side. Slowly, the TV lifted out of the credenza.
She was both shocked and embarrassed. It was all over her face. I explained, " It isn't about luxury it's just simply a lack of space." We had had a great time making fun of Valentine's Day. We bought cheesy gifts, we had met someone new- a win on all accounts. I had to get one more jab in. I slowly flipped her a bird off the end of my nose.
She looked nervous for the first time of the night. "I need to ask you a question."
"What's that?"
"Where I inquire about a topic with the expectation of a statement in return." I laughed. She couldn't have been too nervous.
"I have never seen a boat like this. I don't know if I will ever have this chance again. I would really like to stay on the boat for the night."
I quickly thought about it. There really wasn't any reason she couldn't. More than one friend had had a few too many and ended up in the forward state room.
"You need to text your friends."
She sent the text and her phone immediately rang. She described how her night had gone up until that point. Her friends ribbed her a little. "It isn't like that," and then she hung up.
"Can I take a shower in the forward (she emphasized sarcastically) head?"
"Sure." She started down. "Towels are in the locker to the left."
"I don't see a locker."
"Closet. The closet on a boat is called a locker. Push the button and it will open."
"Got it" she called back.
While she showered I made 2 more gin and tonics. I found a cheesy romcom. I sat down leaning on the left arm of the sofa. When she walked back up, she had changed clothes. I teased her.
"Did you have to change from pajamas to pajamas?" I was still in my golf pants and t shirt, barefoot as usual. She got brave, "Kiss my ass!"
Her pajamas were pretty, exactly what you would expect girls to wear to a sleepover. It was an ivory short set with a camisole and satin shorts overlaid with lace. It laid beautifully, complimenting her dark skin.
I handed her her cocktail. This time when she sat down, she did not sit away from me. She sat leaned up against my right side. I started the movie.
My arm eventually grew tired and I raised it up to rest on the back of the couch. She leaned back further, now nestled into the crook of my arm. She rested like that for a while. After about 15 minutes, she reached up and grabbed my arm pulling it down over her, my forearm laid against her chest and my hand rested on her stomach.
I had forgotten she hadn't worn a bra all night, until that moment. Her camisole separated slightly from her chest. Her nipples were puffy with a perfect point, pointing high, and the breast round and heavy underneath. They were darker than her skin. Her breasts were no bigger than a B cup.I was embarrassed for noticing.
Eventually, she slid down further and rested her head in my lap. She brought her right arm to rest under her head, which had her hand resting on the inside of my thigh. She softly began to rub. At, first, I wasn't sure that I actually felt what I felt. But the rubbing continued, softly.
I felt the electric shock of testosterone and adrenaline course through my groin. I began to grow hard and erect. I was terrified. We had been having great time. I didn't want it to end in awkward embarrassment. I knew if she kept rubbing, she would feel it.
Not long after that, I swelled to the point of obviousness. I don't know if she felt it on her head or hand first. But, she placed the tip of her thumb softly on the very tip of my erection and rubbed in slow circles.
I felt myself begin to drip. My golf pants were thin... and khaki. There would be no way to prevent an inevitable wet spot. She slowly rubbed my tip with her thumb. After a few minutes I knew it would be there. I faked having to shift. She lifted her head, and there it was, a small wet spot on the front of my pants about the size of a nickel.
She looked down and saw it there, in line with where the tip of my now very erect cock pushed into my pants. She slowly leaned down and kissed the wet spot. I don't know if the world moved in fast forward or slow motion. She reached for my zipper and slid it down. She reached inside and the button fell open. She reached through the opening in my shorts and my erection unceremoniously popped out.
She slowly placed just her lips on the dripping tip, and pulled slightly. The drip stuck to her lips and left a string as she backed away. When it released, she softly cleaned her lip with an index finger and licked it off of her lip. I was everything, shocked, amazed, in wonder.
She slowly grabbed the shaft and squeezed slightly. Another drip emerged. She began licking softly at the base of the shaft. Her tongue was wide and soft. The pink contrasted her dark skin. It occurred to me I had never seen that before. She let the tip of my cock rest on her tongue. The drip fell off onto it.
She opened her mouth and took the head in. She let it sit there for a few seconds then pulled away slowly. "I'm not very good at this." She slid off the couch and kneeled in front of me. I slid down slightly further. The movie played in the background.
Again, she opened her mouth and took me in, not really deep but past the head. She squeezed slightly on my shaft while her mouth slowly worked up and down. I had to be dripping more now. She had to be aware of it. As the moments past, she got braver taking a little more and letting her hand slide up and down on me. I felt her intentionally squeeze the base and pull the pre cum up into her mouth.
When she spoke next, her cheeky confidence had turned to insecurity. "No one has ever, you know." She looked shy with her head cocked to the side. "You know, in my mouth. But you can if you want." My brain was on fire. I briefly remembered her telling about her awkward experiences with the boyfriend. I didn't. I wanted to see what would happen next. It didn't take long.
She stood up. "I thought you would."
"Are you disappointed?"
"No. I just know guys always want to be the first at something."
"I'm a little beyond that."
She giggled.
She stood up and pulled my pants off. She straddled me, sitting on my lap. My forearms rested comfortably in the crook of her hips. She leaned toward me. First our lips, then our tongues touched. I loved the feel of her thick lips and soft tongue. My left hand dropped onto a firm, round ass. She scooted closer. I raised my right hand letting my thumb caress her nipple like her thumb had my cock. She didn't seem to mind.
Then, I reached my right hand across my body and between us caressing her right thigh. My hand moved higher up. I whispered, "Tell me no." Through our kiss she said, "yes!" Then she leaned into my ear, "Yes, yes, yes!"
I first placed the palm of my hand on the top of her mound against her clit. I pushed a little. She moved her hips against it. I stretched my fingers down deep between us. It was damp and warm. There were 2 distinct wet spots- one where she was getting damp and one higher up where I had dripped on her pajamas. I let my fingers come in full contact with her pajamas. I grasped slightly, filling my hand with her entire pussy from clit to opening.
My fingers began to explore through her shorts. The satin was soft and the lace added texture. Her lips felt full and wide. I let the side of my index finger trace up and down her slit. It slid easy. I drew the picture of her lips in my mind.
Her pajama legs hung slightly loose against her thighs. I reached up under the left leg with my right hand. Then, there she was, unobstructed, soft, full. I rubbed gently. She got wetter. Then, it happened. Her lips opened for my hand. She pushed slightly. I allowed my middle finger to slide into her while I continued to press gently on her clit with my palm. Her opening got wider. My index finger slid in as well.
She moved against my hand, a slow forward to back circular wave that continually had my fingers moving inside of her without ever actually pulling them out. I curled my fingers slightly, rubbing against the back of her pubic bone. She moaned and continued to circle. She went from damp to wet to soaking my lap. Our kiss never broke.
She stood up and pushed her shorts down over her round ass. They fell to the floor. She straddled me again. She reached under my shirt placing her hands firmly against my chest. I retreated my arms, allowing her to lift my shirt over my head. It landed on top of my pants in the floor. She crossed her arms and removed her top. For the first time, her breasts were completely unobstructed.
"I want to feel you against me," I whispered.
She pressed her chest into mine and I felt her nipples against me. She wrapped her arms around me. I stroked the back of her head.
"Do you have anything?"
It took me a few moments to even realize what she meant. I cracked the slightest smile. "No."
She looked only a little discouraged. "I've never not used protection."
I processed it.
"Never?"
"No." Then slowly, " I need you to tell me I can trust you."
I cupped her face in my hands. It was the first time we had really locked eyes. They were full of life, and excitement, and passion, and surrender. I could see her thirst for knowledge, her cheeky sense of humor, her desire to love and be loved. "You can trust me. You can absolutely trust me."
She had been sitting with her pussy pressed up against the base of my cock, her lips surrounding my shaft. She shifted and slid herself higher on me. Then higher. My head landed between her open lips. I could feel the slight pressure of her opening. Then, she moved downward. She penetrated herself with my cock. In one smooth easy motion she took me all the way in. She was soft, warm and amazingly wet. I felt her full lips against me as she settled onto my cock.
When she hit bottom she stopped for a moment. We both inhaled deeply. My hands naturally made their way to her hips. Again, she began the slow rolling wave motion. I caressed her nipples. We kissed deeply and passionately. Her pace quickened. She began to pant softly.
Her movement became less circular and more linear, more forceful. There was a defined stop of each thrust as she would push into me and I would come up to meet her.
After several minutes, she took my right hand in her left. "Hold me tight." She leaned back. She reached deep between us. She caressed the base of my shaft for a moment. Then, she began rubbing her clit. Slowly, then faster. Her hips were now thrusting, her small squeaks had intensified to moans.
She forced herself down on me, hard. She tensed her entire body then collapsed against my chest. She wrapped her arms around my shoulders and pulled into me. I thrust hard into her pussy. It tightened at the base of my cock and she squealed. We sat suspended in time for a few moments. I felt her wetness all around me.
"Well, that was embarrassing," she mostly giggled.
"Not at all," I replied. "But, it was hot."
Her voice got raspy, fun and flirty. "Now you," as she began the slow roll again. "Just reeeeemmmemmmbeeeeerrrr..." her voice got soft and trailed off.
Her wet pussy continued to massage my cock. She was still closed tight at the base and wide open inside, one of my favorite sensations. She kissed me deep and then blew softly in my ear. I shuddered.
Her hands were on my chest and my hands were resting in the curves of her hips when I first felt my own orgasm begin to build. "I know you're close. I can feel you," she whispered. She looked into my eyes. "Do it. I want you to." Her pace didn't waiver. Her hips moved over me.
She looked back into my eyes, "In me. Do it in me. I want to feel all of you. I'll take care of it in the morning." I realized the irony she never could, but now was not the time for conversation. "In me," she repeated, softly.
She quickened her pace again. Again, it became more linear. I tensed. Her words were decisive, "Don't pull it out! I want it in me." As I felt my orgasm begin, I pulled hard on her hips. She relaxed her thighs and let her weight rest on me. I slipped in ever so slightly deeper.
I began to pulse inside her. She moaned and threw her head back, then kissed me deep.
She sat in my lap for several minutes, me still inside her. The credits rolled. We kissed. She lifted off of me slightly. My cum came flooding out of her. She stood up. "I will take care of that in the morning."
"There is nothing to take care of." She looked at me, puzzled. "I can't get you pregnant. Shootin' blanks since 2007." She smiled then giggled. The mood immediately returned to light hearted and fun.
"Well, I guess I'm sleeping in your bedroom tonight."
"Stateroom, it's called a...." my voice trailed off. It didn't matter. She was already halfway down the aft stairs. My cum, running down the back of her thighs shimmered in the moonlight shining through the salon windows.