This was not a trip I had looked forward to taking. Mother's Day was approaching and I was due to fly out of Long Island for Tampa-St. Pete to visit my mom in the Alzheimer's wing of the residential hospital where she has had to live (if you can call it that) for the past ten years. At least my visits to her would be merciful insofar as my time with her would be relatively short. Her best, most lucid periods occur in the morning to early afternoon and by then, she becomes tired and begins to hallucinate. Besides that, she might or might not recognize me. Still, I planned to spend my mornings with her and to even take her outside pushing her wheelchair. And, without going into the exhausting details of my visits, that is exactly what I did. Unfortunately, she had declined rapidly since my last visit a few months ago and I dreaded to see my mother in this pathetic condition.
I had another problem that was upsetting me. I was having a problem with my penis. It began not long after my very difficult and upsetting divorce. I went through several years of deep depression. I understood my penis problem to be psychological but I couldn't seem to overcome it. I just couldn't seem to get hard when I needed to be hard. I realized that at my age, this problem can occur but even with those little blue pills, I wasn't able to keep my mind focused lomg enough to fuck. Oh, I had no problem jerking off. Believe me when I tell you that I jerked off plenty, at least once a day. But when in bed with a luscious beauty, I couldn't stay hard enough to slip it in. In spite of this, I always hoped to find a woman with the stamina and patience to get me off. If only...
My evenings looked to be more entertaining. My dear friend, Alvin, owns some investment properties on Longboat Key (off the coast of Sarasota) and he suggested I stay in one of them while I do him the favor of eye-balling his other properties on the island and reporting back. I have only been to Longboat Key once before and while it is a sleepy little island, it does have some cool bars and restaurants lining its pristine, white powdery shores. It's very close to the action on Lido Key, Siesta Key, Anna Maria Island and Sarasota and it has a spectacular sunset...right on the beach in front of the house. This had all the earmarks of being a much needed vacation.
I flew in on a Wednesday, picked up my rental car (fortunately, a convertible black Corvette) and headed over to see Mom. After my depressing visit, I drove an hour further south to Longboat. The house was quite beautiful. Sitting on the northern tip of the island where the Gulf of Mexico meets the bay channel that separates Longboat Key from Anna Maria Island, it was a large house with three bedrooms and an infinity pool gulfside. This house had some incredible view and I was certain that the sunset would kill. After settling in, I rolled up a joint and strolled out onto the beach where I met a young woman sitting on a blanket in front of the neighboring house. I politely introduced myself.
"I'm Caren. I don't live here. My friends own this house and suggested that I stay here for a few days to relax because I am ending an ugly divorce and I need some r-and-r. Whew, that came out in a rush! Where did that come from? Maybe I need a hit off that." I smiled at her and handed her the joint. I thought I felt her tremble when she took it.
"I'm Ray and I don't live here either." I explained the purpose of my visit and suggested that perhaps she might like to join me for dinner. She was hesitant at first but when I explained that it was nothing fancy, just a short trip over to Anna Maria to one of the best barbeque joints on the planet, Mr. Bones, she accepted and we made a date for six o'clock. In my short time chatting with her on the beach, I made a detailed perusal of her fineness. Also, I quickly became enamored by her sense of humor, her easy conversational way and her seemingly lack of inhibition. She was a breath of fresh air blowing in off the Gulf.
During the superb dinner we got to knew each other a bit more. I found her to be wonderful company after she loosened up with a couple of margaritas. She was entertaining and fun with a good hearty laugh. She talked a blue streak and while I didn't care a whit of what she said, I enjoyed watching her. I discovered that she was 34, was married seven years and just ended an ugly three-year divorce; she was from Baltimore originally (which she hated) but now lived in Chicago; that she was a legal secretary; that she caught her ex having an affair with an old girlfriend; that so far her trip had been uneventful and that she spent much of the day meditating on the beach and doing yoga exercises and, oh yes, she hated her ex (did I mention that?). Visually, she was stunning; small and thin, lithe, long brown hair, and a perfectly proportional body. I especially liked the way her cleavage opened into pretty round breasts. She was quite beautiful and looked like a smaller version of Sandra Bullock. But she babbled. A lot. Maybe it was some nervousness or some anxiety about being with me. I let her roll along and stayed interested in what she was saying, asking a lot of questions and then listening intently to the answers.
After dinner, we drove back to the house and I invited her over for a nightcap which she readily accepted. I poured myself a glass of cognac and poured her a glass of white wine. We sat down on the moonlit deck and continued our conversation. She produced a large, thick marijuana joint and we spent the time pleasantly. The combination of the pot and the cognac had a fast affect as I watched images shift around me. Fortunately, it had the same affect upon her and soon Caren and I were laughing, singing, giggling and becoming very touchy-feely familiar. She walked over to the pool and dipped her toe into the warm water.
"The water is so warm. At my house, the pool is broken and empty and waiting for the repairman. I admit to sneaking over here before you arrived and skinny-dipping a couple of times. It was spectacular at night in the darkness. Please don't say anything, okay? I wouldn't want anyone complaining to my friends."
"On the contrary, I'm glad it was here for you to take advantage. I'm only sorry I wasn't here to see you naked! I skinny-dip all the time."
"Wanna? I love to skinny-dip in the dark. I'm not shy! I'm on vacation!" she said as she untied her wrap and stood in front of me in her dark blue bra and bikini panties. She looked over at me, "So are you going to sit there and stare at my tits or are you going to join me?"
Snorting, I stood up and pulled my shirt over my head, I dropped my slacks and, as per my usual tropical attire, that is, not wearing underwear, my seven inches popped out erect. I was not concerned about hiding it and I made a big show of jumping into the pool. I watched as she pulled off her bra and stepped out of her panties. Her breasts were so beautifully young and firm and her nipples pointed up to the starry sky. Her pussy was trimmed in a narrow landing strip. She undressed quickly and jumped in.
"You know, for someone who is 25 years older than me, you are in terrific shape."
I mockingly flexed my bicep and she wrapped her arms around it in order to hang from my arm. I felt her breasts brush alongside me and it felt fine. We splashed around the pool teasing each other. I grabbed her once and ran my hand up along her leg, over her ass and onto her back. She was very receptive. After a few minutes, we were huffing and puffing as we made our way to the shallow end. We leaned against the side while she inspected my body.
"I like the way your...," she searched for the right word for a moment "...cock...looks." She smiled at herself and then repeated, "I like the way your cock looks. My ex was my first and only so looking at you is kind of educational. My ex had a small, thin penis with a foreskin. I never really liked the way it looked and I could hardly feel him inside of me. You, on the other hand, your cock is…"
"Yes, speaking of the other hand…" I took her 'other' hand and wrapped it around my thick cock. "There, is your curiosity satisfied?"
"No, not yet!" She used both her hands to feel and fondle me. "So big and thick..." I pulled her over to the pool's edge where it was shallow and let her explore. Meanwhile, I began to explore, too as my fingers danced over her breasts and her nipples, occasionally tweaking them.
"I know you won't mind but I just have to do this." She lifted her legs up and wrapped them around my waist. I leaned back against the coping while she slipped me inside. She felt tight and I liked that but, to be honest, I was really hoping and praying that I could stay hard. So far, so good.
"Oh… oh… oooh… now that's how a cock should feel… oh my goodness… oh, that is good." She looked up at the sky and shook her head. She had a look of amazement.
"What is it?"
"What is it is that I just met you today and now your cock is inside me. This is so unlike me, I swear. Usually, I push men away but you...you make me feel different - maybe a little crazy and maybe a lot horny. I feel so loose with you. Really, I'm not
like this." She seemed to have second thoughts when suddenly she smiled. "Shit, I'm on vacation. Why shouldn't I get a little crazy..." In response, I began to bounce her on my dick. She hiccuped and gripped my body. She swooned. "Please… don't stop… please make me cum… please…"
I took her nipple between my lips and energetically suckled it. Her response was to tighten her pussy around me. She was grinding me when she began to cum in squeezes, tight clinches and soft moans. Her tight little vagina wrapped around me like a velvet glove, albeit a very wet one. Within only a few minutes, she was bucking me and luxuriating in the throes of an oncoming orgasm. I felt her insides warm up as I arched my back and shot a small load. It was more like a low-caliber shotgun shell. Spent, she clung to me. I felt her heart pumping. More to the point, my penis stayed hard through it all, I had a small orgasm and I was still hard! Thank you, Lord.
For the first time that night, I kissed her. She responded by inserting her tongue and swabbing my throat with it. We must have kissed like that for a while because our skin began to prune up. Taking my hand, she led me up the pool steps. I took her hand and led her into the house where I pulled some towels and dried each other off. I refilled the glasses and she relit the joint. I dimmed the lights and the huge floor-to-ceiling windows revealed the twinkling starlights. We lay on a large throw that covered the large leather couch and made small post-sex chat.
"I never came before that way…I mean, with a dick inside me. That was a first and it was wonderful." She leaned up to ear and whispered, "Thank you" in a husky, sexual tone. She turned quiet and lost in thought. "My ex just couldn't make me cum - and this goes back to when we were still in college. Either he didn't have enough patience or maybe he just had no skills. I know that my skills were minimal, at most. But I used to fake orgasms to make him feel good. I figured that this was how sex was supposed to be. What did I know? The only way I've ever had an orgasm is either with my fingers or with my vibrator."
I cradled her in my arms and sensuously ran my hands along her, touching and caressing ever part of her. My fingers diddled her clit and she responded enthusiastically. I did this several times until I began to slide my way down. She lay back and looked positively delicious with her long hair spread along the couch. I kissed and licked her breasts for the longest time. One of my favorite things is to lick under the breast along the line where the skin meets the chest. I find it to be one of the best and most responsive parts of a woman's body. Caren responded the way I hoped she would, by arching her back and pushing her breasts into me.
I licked down to her navel and spent some time there until I got to the top of her landing strip.
"Do you like my design? I did it just before I flew down."
"Yes, I like it… but I like this better." My fingers spread her labia to reveal her little pearl of a clit which I then gently sucked in between my lips.
"Oh! Oooh! Yes!...I like that better, too. Yes."
The tip of my tongue traced circles around it and I could feel it fill with blood and stiffen up. Oh, that felt good.
I concentrated on licking and nibbling every inch of her pussy, her canal, her taint and every-so-often around her pucker. Each time I did that she pushed her butt against me and allowed me to prowl around a little deeper. Then I worked my way back to her cunt and began to seriously appreciate it. Her pussy was small, tight and compact. With my lips around her clit and my nose in her cunt, it was a good fit. She squirmed around my face and when my tongue began to lash circles around her stiff little man-in-the-boat, I began to drown in her gushing cunt and her orgasmic groans. This woman had just cum, really cum, I mean, buckets of cum… and I was glad.
She crawled onto my chest and began to kiss and lick my face. "That was the best orgasm I think I ever had. You can go down on me anytime, mister. That was fucking awesome."
"Thanks, that's a nice compliment. I must say that your pussy is especially delicious."
"My ex didn't think so. He hated going down on me as much as I hated going down on him. He used to make me feel dirty and smelly. You, on the other hand, just made me feel exquisite."
"And I'm only warming up... But you have to stop comparing me to your ex or even reliving past injustices. Forget about the jerk. For you to really enjoy this, you have to just close your eyes and it flow. Like the Beatles said, 'Relax your mind and float downstream.' Let the orgasm wash over you. Then we'll see how good it is."
I rolled her onto her back and quickly rolled on top of her. Her legs spread wide as I slipped into her, pushing my still stiff cock as far as I good. She gasped and pulled her muscles in, sucking me deeper. "Oh, that feels so good… your cock feels so good in me… so this is what it's like. And here I was thinking of going lesbian."
I laughed. As I continued my leisurely fucking of this oh-so-sweet cunt, I made a suggestion. "You should try it, I mean, having sex with another woman. It will be good for your head and your self-esteem. It will make you a better lover. And you'll love it."
She rocked under me, her vagina gripping me and sliding me deeper as she rotated her as under me. "You'd like to see me eating pussy, huh? Maybe I already have..." She paused for a moment. "Me and my college roommate played together a few times..."
"All I'm saying is that as long as you are now divorced, live out your fantasies. Do whatever you want and who cares? Be who you really are and stop worrying about what was. You ever hear the saying 'When your past calls, don't answer. It has nothing new to say.'"
She smiled. "I like that." She persued the conversion, "So I take it that you've lived out your fantasies ever since your divorce, am I right? Did you go to an orgy... or have two girls...' She thought a moment. "You've experienced a man?"
"Indeed, I have. I've done all those things and you know what, it was all great. It added new skill sets. Caren, I've done it all."
"Well, do it all to me. I'm loving this. Let me kiss you."
I leaned down and we began to do the horizontal bop. Our kisses were torrid. Her body was writhing beneath me, wrapping a leg around my ass and pulling me deeper to one side. Sometimes, she seemed to be climbing me. I began to hump harder as I felt my cockhead swell up and slide over her g-spot. We were both panting and sweating; our fucking was animal. She seemed so feline, crawling around my body and finding her way into every private crevice. I pumped hard until her pussy squeezed and pulsed around the shank. I began to explode volleys of viscuous jizz into her. Her velvet walls pulsed around my meat as she was cumming, too, and cumming hard. I had some difficulty holding on to her and staying inside. Together, in the good-old missionary position, we'd orgasmed at the same time...again, this time only better. Holding each other, with her legs wrapped around my waist, we slowed down. Bathed in sweat, we kissed again, only this time with a deeper passion.
Finally, we came up for air. "That was the best fuck I ever had. Honest. One hundred percent true. Even better than the last one, which was great. Even by myself, I never came like that. We came together, it was so good. I let myself go... go with you. I just love sex with you, Ray. For an older guy…"
"Don't go there, Caren. I've been feeling my age lately but tonight, right now, I feel like a kid again and I'm almost ready to fuck you again."
"Really? Again? I like the sound of that but you need to give me a rest. I need time to recuperate from that. My vagina is still pulsing. And I need to clean myself up down there before…"
"No, no, no, dear girl. I will clean you up."
"You would, with all that cum down there."
"I would indeed. It's delicious. Maybe you'll clean me off, too."
"Hmmm… maybe I will. With you, I feel like I can do anything..." She nuzzled into me and we lay there entwined and quiet for quite some time until we felt her begin to drip onto our legs. I quickly spun around and buried my tongue into her pussy, lapping and sucking out our cum. I licked and bathed her upper thighs as she squirmed and rolled around. Finally I fell back onto the bed.
She touched my semi-limp penis and gently caressed it. My eyes were closed as I enjoyed her tender touch. Then I felt her tongue begin to lick and swab the head. I reacted by arching up and pushing it in. She began to explore my cock and each time she got to the head, she took me in a little deeper. She seemed to be experimenting by the way she buried her face in my nutsack and sucked in my balls, first one and then the other. Her tongue traveled up to and near my asshole but never got that far. Her index finger did however find its way in a little bit which only made me harder inside her mouth. She was now stroking me up and down while sucking on the head.
"Keep doing that and you'll get a mouthful of cum. I'm getting close."
"That's what I want. I want you to cum in my mouth. I want to taste it. Cum in me."
"Just keep stroking and sucking on me… and push your finger into my ass some more. Yeah, like that. Uh, huh… Oooh, that's good." I began to fuck her mouth with a distracted intensity. Her lips sucking on the head and her tongue whipping around it was too much for me. She had turned this blowjob into an art form and and I let forth another volley of cum. This orgasm was not as voluminous as the last but she was rewarded with several large globs of my goo. I quickly pulled her to my face and mashed her into a kiss. Her mouth was sloppy with my cum and I licked around her tongue and her palate. She moaned softly as we sweetly kissed and gently caressed each other.
"You're so good."
"Ever think that maybe it's you?"
"No, it's not me. No one ever told me I was a great lay." She spoke quietly while nestling in my chest. "My ex said I was the worst, like a dead woman in bed, that's what he called me. And since then, to be honest, sex hasn't been so great. I have more fun with my vibrator." Her voice trailed off in a sad way.
"Well, for one thing, it seems obvious to me that your ex didn't know what he was doing. You are a great lay and that was some excellent blowjob. Your ex was probably more concerned with his own orgasm and then rolling off you and going to sleep. Most likely, he used you to get off and then left you high and dry. You didn't marry the man who cared enough to learn how to do you the way you like. But that was then and this is now. You are a great lover so don't sell yourself short. Your pussy is like apple pie and your ass is like ice cream. You do it right for me... and I'm a connoisseur."
"I'm so glad that are you so different. You certainly do me right. And really, we don't even know each other...so maybe you're right. Maybe it was me, too." Her smile covered her face truely from ear to ear.
"Well, of course, that's what I'm saying. The fact that I'm an older guy probably was not intimidating to you. Plus you were a little drunk and stoned when we first skinny-dipped. Your guard was down, your defense mechanisms weren't working at full strength and you fell prey to my manly wiles. I had to have that body. Admit it. Admit that I seduced you, an innocent waif."
"No, I think I first wanted to fuck you during dinner...way before dessert." She grinned.
She got up off the bed. I reached for her but she backed off. "No, no more for me. I'm going to find my way back to the house, take a shower and pass out. I have some things to do before I crash, too. What's your schedule like tomorrow?"
"My schedule is the same for the next week. In the mornings, I go up to St. Pete to see my mother. Then I head back or wherever I feel like going. Why?"
"Well because I'll be busy tomorrow. I'm meeting a girlfriend in Sarasota who is taking me shopping. But I want to see you again. I want you to fuck me limp again. So here's my idea. Tomorrow, I'll pick up a bottle of wine…"
"…red wine and Chinese food and I'll meet you here for dinner and dessert." She was getting dressed.
"That's rather presumptuous, don't you think? Maybe I'll have company, maybe some strange tail…"
"I don't care. I'm here for five more days and I want more of your cock, your mouth, your hands, your man-ness, the whole package… and I want it every day. I'd even agree to sharing you but you won't want anyone else. You're going to love fucking me, admit it."
"What nerve!" I jumped out of bed and chased her out of the bedroom into the living room where I caught her and spun her around into my arms. I held her close and looked into her eyes. "I'm gonna fuck you silly, little girl. You'll fly home limping, your pussy will be on fire. I promise, you'll remember this vacation."
She kissed me ferociously and I responded in kind before she turned toward the front door. "That's just what I want to hear, Ray." I wrote this story for a girlfriend who asked me how I viewed love. This was my response.Is there more to come? Like Mr. Fox's Chocolate Syrup, U-Bet! Stay tuned for Part Two.
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<a href="https://www.lushstories.com/stories/love-stories/a-gulf-coast-welcome-i.aspx">A Gulf Coast Welcome I</a>