Last Night in Paradise

Buildup: Our last night of vacation — once again, we over-indulged in food and drink at dinner. I was determined to have one last tropical romp, and when B came to bed in only panties, I was sure she felt the same way.

Foreplay: B fell back on the bed — her arms and legs spread in a sleepy, drunken, inviting way. I leaned in to lick each of her nipples in turn and she let out an audible moan. Encouraged, I started to rub her pussy lips through the lace of her panties, but she surprised me by asking:

“What are you doing?”

Main Event: I pulled her panties down her legs and off her ankles. I positioned myself between her spread thighs and as I entered her in a swift stroke, I answered:

“Making love to you.”

I guess the sounds she made as I tongued her nipples into stiff points were an indication that she had some idea what I was up to. The way she pulled her knees up and let me drive into her with drunken abandon tipped me off, too — and when she used her powerful Kegels to squeeze my rod inside her, she got me off as well.

Afterplay: Having learned my lesson the other night, I tried my hardest to make sure I could return the favor and make B come. I tried every combination of fingers and positions that I could, but while each new touch got an appreciative squirm, nothing led to the kind of rhythm that would finish her off.

I went to fetch something outside the room, and when I returned I decided that the final night deserved one more try. I slid two fingers into B’s still-slippery slit and spread them side by side, earning a welcome grunt from B in her sleep. Keeping her filled, I stroked her clit in a constant light motion — she was awake now. I hooked her with three fingers — my thumb between her labia as I rubbed her button with two fingers. With my left hand I spread her ass and let my other thumb rub her juices over her taint before plunging deep inside her. B was gasping and squirming now as I stroked her clit from side to side with two fingers. When I felt her about to come, I strummed her clit in double time and brought her to a double-strength orgasm.

Afterglow: We had nothing left — we fell asleep hard, our sweat-slick bodies cooling in the noisy hotel air conditioning.

Rating: ★★★

Dessert

[That was quite an appetizer, no? Over two months between entries! Hope you find this nourishing---]

Buildup: On the way to dinner, B and I discussed the legs-over-the-shoulder position we had just tried — I thought that the angle of penetration might have been better for her (it put some interesting pressure on me) but she confessed that she needs the contact as well as the penetration for it to be good for her. “Or is that too much information?” B asked.

I surreptitiously pulled her hand to the swelling in my pants. “No, that’s the perfect amount of information!”

There was powerful sexual tension during dinner — our dining companions knew exactly what we had been up to, and very shortly worked out that B had been left hanging. After dinner, we stopped at a poolside bar with swings(!) instead of bar stools. At one point in the evening, B was straddling me on the swing — a fun scenario, but maybe not so much with everyone else at the bar (we obviously weren’t so shy as to avoid getting our picture taken.)B was over the two-drink limit, but I could tell it wasn’t going to be a problem — especially when she pulled up her top to flash me as we walked back to our room.

Foreplay: Back in the room B changed from her tank top to a thin camisole, still wearing pink lace boyshorts, and lay back on the bed. I knelt between her legs and pulled her panties to the side so that I could lick her glistening pussy — she let out a moan. I lingered there with my tongue as she sighed, then I crawled up to give the same attention to her nipples. I grabbed the bottle of massage oil at the side of the bed and began to spread it over her chest, feeling her rock-hard nipples in contrast to her pillow-soft breasts. I straddled her waist and shifted my hips forward to bring my throbbing shaft between her cleavage — squeezing her boobs together and pinching her nips as I rode back and forth. I didn’t want to come on her neck (and leave her hanging again) so I frantically pulled off her panties.

Main Event: B threw her legs in the air around me as I started into a hard grinding missionary position — I was determined to give her contact and penetration! Her breath came in gasps as I pounded her into the bed, and I asked whether this was working for her. She shook her head and I asked, “What do you need?”

“Get behind me,” she growled.

I flipped her over and she got on hands and knees as I slid back between her folds and started fucking her doggy-style. After slamming into her for several strokes, I slowed my pace — keeping my hard shaft inside of her — and reached around to stroke her clit. B pushed back urgently against me, trying to take me deeper inside. I took the hint and resumed pounding, finishing yet again before she had come.

Afterplay: B rolled to her side and fell asleep, ignoring my initial probes with my fingers. Soon she awoke again and started clenching as I brushed against her clit. I used the thumb-in, fingers-strumming right hand hook, and all of the previous activity of the evening had her ready and working for her O. When I brought my left hand down her ass crack to tease her from behind, she exploded — throbbing and clenching on my fingers.

Afterglow: Sweaty and sated.

Rating: ★★★★★

Appetizer

Buildup: We hadn’t had an opportunity to make love for a couple nights after our Christmas morning quickie, and after a sunny, hot afternoon of sightseeing we were both warmed up. B was wearing a simple black tank top that framed and displayed her boobs invitingly, and we each playfully felt the other up on our tour bus. We found ourselves with a little bit of extra time before our dinner reservations, so….

Foreplay: Back at the resort, B quickly took off the day’s clothes and lay on our hotel bed. Truthfully, I was not yet in the mood — thinking ahead to the night — but B was obviously ready, and as I looked at her displayed on the clean white sheets, showing an even-more-tightly shaved landing strip, I decided she looked good enough to eat.

I knelt between her parted legs and brought my face between them — starting by licking along the smooth skin just inside each of her thighs and releasing a hot breath over her pubic hair as I moved from one edge to the other. Next, I ran my tongue lightly along the edge of her outer labia, which were still pinched together — but not after the next stroke of my tongue, which parted her lips from bottom to top (back to front). I settled in to tease her clit with flat strokes of my tongue and brought two fingers between her legs to fill her as I licked. B was squirming under my attack, punctuated by electric jolts when my tongue found a particularly favorable angle. She tried to pull me up, but I held her hips down with my arms and tasted her a litle longer before climbing up.

Main Event: B’s legs were spread wide and I entered her in one wet thrust. We pulled a pillow under her ass and I pounded into her with her legs high in the air. Inspired, I took her ankles and lifted them over my shoulders — grasping her thighs and pulling her against me as we fucked from a steeper angle. It worked well for me and soon I exploded deep inside B’s pussy.

Afterplay: I knew B hadn’t come yet, so I immediately pulled out and returned my face between her legs to continue licking her. Again, she twitched as my tongue flicked her clit but a rhythm was eluding her. I switched to using my hand instead, and tried several combinations of fingers and positions to see if I could make her come as hard as I had.

Too late — B’s mind was already on our dinner reservations and whether our dining partners would notice that we were late. (I knew that they had already granted us extra time but B didn’t realize that.) I begrudgingly stopped my caresses and promised to finish what we started after dinner.

Afterglow: None. Time to catch up with our friends!

Rating: ★★★★

Open Me First

Buildup: Christmas morning, we found ourselves in a tropical hotel room. I had slept in a little bit and B was already in the shower. We were supposed to meet people for breakfast, but B surprised me by suggesting a quickie!

Foreplay: None. The proposition itself was enough to arouse me — and obviously B had been thinking already!

Main Event: B unwrapped her towel and lay back with wet hair on the hotel linens. I rose above her and pumped slowly and steadily, as I looked down at my cock sliding in and out beneath B’s trimmed landing strip. B moved me along with well-timed Kegel squeezes, and I leaned forward as I came, grunting my approval into B’s ear.

Afterplay: None. We were late for breakfast.

Afterglow: I lay back on the pillow while B got dressed and realized I was hungrier for sleep than food — she went on without me and I caught another hour of rest.

Rating: ★★★

Old Faithful

Buildup: The reason I had been able to catch up on last month’s sex life was that I had been sent to a week-long seminar out of town. Of course, writing about the sex I was no longer having is a recipe for blue balls, and an undercurrent of unfulfilled horniness ran throughout my business sessions during the day, and my dreams at night. To make matters worse, B and I never seemed to be able to sync up our schedules to talk on the phone, and when we could, never had a decent mobile phone signal. To make matters more intense, I decided that I wasn’t going to come unless and until B was directly involved (as opposed to merely being the object of a solo masturbatory fantasy.) On my last night of the trip, I had visions of doing some kind of joint cam show. I set up my laptop and webcam at the edge of the tub in the hotel bathroom and waited, absent-mindedly stroking myself.

And waited.

And waited.

His Turn: While I waited for B to log on, my mind (and hands) kept drifting back to our last time together in our tub — in particular, the “continuous handjob” that B gave me during foreplay. I poured some of the hotel’s shower gel onto my hands for lubrication, and tried the same trick — bringing my hand on a downstroke from tip to base, then following with the other hand in the same motion. Without B’s words of encouragement, though, I was having a hard time staying hard. (A soft time?)

And when B finally logged on, a) she was fully clothed at our home computer, and b) the connection kept dropping. Undaunted, I told her to turn the camera off on her side to conserve bandwidth, and I offered to forge onward. I started describing for her the scene I was playing in my mind. I kept listening for her to pick up the theme and talk me through it, but her head was not in the same place and she wasn’t as ready to go as I was ready to finish.

They say a stiff prick has no conscience, and I guess that’s true even for self-control. If B wasn’t going to do the coaxing, she could still be involved as a voyeur. Instead of thinking about B at the other end of the line, I closed my eyes and remembered B at the other end of the tub. Suddenly, my dick swelled and I realized I was moments from coming. Down, down, down, down, my soapy hands came over my engorged cock, and then — a geyser.

The first spurt was hot and clear, and shot nearly four feet into the air. The next spurt of white spunk also fired a foot or two into the air, followed by three or four more spurts exploding and receding over my hands and into the bath water. B couldn’t help but laugh out loud. I just kept saying, “Oh, wow” — even as horny as I had been, I had no idea how much pressure had built up.

Now B wants to nickname me Old Faithful.

Cam Girl

Buildup: Several days into my business trip, I found myself endlessly replaying the visuals from our night in front of the bathroom mirror in my head — I went to sleep with a raging hard-on, but not before leaving B a desperately horny email begging her to call for some phone sex if she was feeling the same way.

I wasn’t there when she called, but her voicemail said that she had been prepared to do a webcam striptease. (We tried that once before with mixed results — I kept pushing for on-screen vibe action, instead of being happy with the bouncing boobs on my computer screen. This time I vowed to appreciate whatever B had to offer.) I whipped off my bathrobe and IM’ed back, hoping I would catch B at the computer and in the mood.

His Turn: I got a window on our bedroom with a minimum of technical difficulties, and in no time B had already peeled down to a pink bra and matching lace boyshorts. There was no shyness or reticence in her voice — she was there to get me off, and I was going to let her. B did a few dance moves and reached behind to remove her bra, then lay back at the edge of our bed like the morning of the very first entry of this diary. I took my turgid cock in hand and began stroking as B pulled a pillow under her head to watch me.

“I wish you could touch me,” she said, as she wriggled out of her panties and spread her legs wide to give me a view of her landing strip. She wasn’t touching herself, but she squeezed her legs together, crossing them back and forth to provide friction on her button. I watched, and remembered all of the times I had taken her in that position, creating my own friction with my hands. I had given up replying and coaxing her, instead pumping my shaft violently.

“If you were here now, I’d put my legs up over your shoulders,” she sighed.

Five nights of semen burst into a hotel towel.

Stiff As A Board

Buildup: During our vacation, we joined another couple for a night of drinks and games. B and I shared a scorpion bowl at dinner and B added a planter’s punch for good measure — back at the shack, she poured herself a healthy shot of Gosling’s dark rum as we played Trivial Pursuit and some other board games. After a so-so session, it was good to be laughing and flirting during the game, and B’s friend teased that we would be making out soon. Well after midnight, we finished our rum drinks and retreated to our room.

Foreplay: In the strange bed, B found my lips in the dark and we began kissing and making out, just as her friend had suggested. B took off my T-shirt and started licking and touching my nipples with her fingertips while I grabbed her breasts through her thin cotton shirt. We kissed some more, and B began squeezing my erect shaft through the fly of my boxers. She slid down my torso as I pulled her shirt up to expose her boobs. She took me in her mouth with long soft strokes, alternating with dragging my saliva-soaked dick between her tits, while I reached beneath her to tweak her nipples and squeezed her boobs together. B’s sexiest new twist on blowjob technique was to grab my ass with her palm and pull me into her mouth.

Main Event: I scooted further down the bed from my position high on the pillows, and B moved into place to make love to me on top. I slid my hands up the back of her legs but she elbowed my arms out of the way before I could play with her taint. I decided to play a submissive role and let B ride me — which she did, good and hard. I couldn’t resist the tits in my face and lavished attention on them with my tongue and fingers, distracting B from her rhythm. I put my hands on her hips and held her so that only the tip of my cock parted her lips, then slammed her against me.

I flipped B onto her back and propped myself above her. Just as I had done from below, I teased her pussy lips and clit with my dick head before plunging in to the hilt. B encouraged me with her hands roaming on my ass — I tried to give her a little extra stimulation with my right hand holding her pussy lips tight just above her clit. I lasted a little longer than usual thanks to drunken numbness, but B’s hands teased me to a long-awaited orgasm.

Afterplay: Given the late hour and the copious rum consumption, successful afterplay seemed unlikely, but I gamely laid my finger and thumb along the line of her lips. B squirmed a couple times but didn’t have the stamina to finish, and I moved my hand to peacefully palm her ass instead.

Afterglow: We feel asleep (passed out?) fairly quickly.

Rating: ★★★★

Red Red Wine

Buildup: Vacation time — I had been in a non-stop low-level state of arousal since the magnificent sex of the landing strip revelation and the usual allure of vacation beds. B not so much — the bed at this place was not so comfy, and in any case she was looking forward to catching up on sleep. As a result, the first two nights passed with no nookie. On the third night of vacation, I got a little anxious and impatient, drinking a glass or two of red wine to get in the mood, and another glass or two after B turned in for the night.

Foreplay: I stumbled to bed — TDTF, but determined to try. B was already asleep, and when I began pawing at her, she was “antsy“. The tried and true method of arousal is to put her hand on my crotch, and she squeezed my hard shaft until she was ready to feel it inside her.

Main Event: Straight missionary — B wasn’t very responsive. I began pumping just to get off, and the combination of the wine and oncoming guilt for waking B when neither of us were that into it caused my hard-on to get progressively squishier. It was at that moment that B started moving her hips and rising against me — that made me come in a semi-soft state and left her high and dry (or high and wet.)

Afterplay & Afterglow: None. Back to sleep for B — me lying awake in the dark, knowing this would be a dreaded 1-star entry.

Rating: ★

Hot Fun in the Summertime

Buildup: Even by the standards we’ve lifted ourselves to (and the blog is still chronicle, not inspiration) this was over the top. [I'm pretty sure this has the most tags of anything I've posted so far!]

Our last day at the beach, still hot from the past couple nights (and days) and we found ourselves with an excuse to leave everyone else at the shore while we returned to the house. A quickie was implied in our eyes, but we had already washed the sheets in preparation for checking out. We needed a clean, possibly vertical, location.

“How about the outdoor shower?” B asked.

Foreplay: We turned on the shower spray and removed our bathing suits. My erect cock glistened in the afternoon sun as I admired B’s tan lines. Unfortunately, there was no bench or other surface to sit or lean on. We tried several configurations of B straddling me while I leaned back, or me holding her up while she propped a leg against the shower wall, or slipping between our intertwined legs. Nothing was working, so B turned off the shower and kissed me while stroking my cock with her hand. Even that wasn’t working — no soap or conditioner in the shower to use as a lubricant.

“Use your mouth,” I implored, and B bent down and took my tool into her mouth. It was mind-blowing (as well as dick-blowing) watching her head bob up and down in the sunshine as she worked her lips and tongue on me. When she pulled off to stroke me again, I nearly exploded in her hand –

But then my neck convulsed in pain.

Several times in my life — always standing in the shower — I’ve gotten a horrible headache/pinched nerve thing when trying to come, either by my own hand or B’s. I had to stop, but I was too close to coming to give up.

Main Event: I twisted my head around to clear the pain, then told B to bend over and prop herself against the shower door. I positioned myself behind her and slid my still-hard rod into her slit. Again, seeing myself pumping into her in the sun was fantastic. Our wet thighs slapped together with each thrust, and I could feel her squeeze down on my shaft when I came.

Afterplay: None.

Afterglow: Less than none. We rinsed off and out our suits on. When we walked to the side of the house, we saw that the housekeepers had come to the house while we were in the (exposed) shower! We ran to the beach before we could find out what they had seen or heard.

Rating: ★★★ (average 4 stars for location and 2 for execution)

Vacation Beds

Buildup: All day long, we’d convinced ourselves that we’d need a night off after a couple of good times the night before — after all, it’s one thing to be fortysomethings having the sex life of teenagers, but it’s quite another not to have the, er, resiliency of teenagers.

No matter. As soon as we got into bed, I was hard and B was wet. There’s something about being in a strange bed in a strange room that is erotic to us.

Foreplay: Some mutual fondling as we each lay on our backs. The immediacy of our responses meant that we didn’t need to spend a lot of time arousing each other.

Main Event: I climbed on top of B and held myself at her entrance while she guided the tip of my dick between her lips and over her clit. When neither of us could stand the teasing any longer, she let go of me and I sank to the hilt inside her. B brought her leg up around my waist and pulled me in with it. I leaned in to kiss her roughly as I thrust in and out quickly. B brought both of her legs up in the air so that I would penetrate her more deeply. Our bodies rocked back and forth as I spurted into her, still kissing and biting her neck.

Afterplay: I rolled over, panting, and placed my fingers where my cock had been. At first, I got no response, but when I drew a slick finger along B’s perineum she began to clench and unclench her muscles. When my fingers went too deep, she lost interest from the excess stimulation, but she liked being teased with just a fingertip parting her pussy lips. I brought my other hand down along her ass to tease her rosebud and strummed my thumb back and forth against her clit hood until she came.

Afterglow: “There’s something very wrong with us.”

Rating: ★★★