Dirt-y Mind

Buildup: We decided to see if Courtney Cox’s new show Dirt to see if it was as “edgy” as previews claimed. Don’t know about edgy, but there was a fair amount of rear-entry sex and hair-pulling — however, we’d had a fair amount of rear-entry sex ourselves over the past few nights. B poured her sexy holiday drink, and I pondered a new position.

Foreplay: B lay next to me on the bed with her hand on my chest, while I rubbed the side of her breast through her nightshirt. She shifted her head down to lick the nipple closest to her, then proceeded kissing down my belly — I cupped her ass cheek with my hand as her head approached my fly. She gave me a quick blowjob through my fly, using her fingers in a tight ring around the base like the last time (it had been a while!) Surprisingly, when she came back up from sucking me, she did not give me the traditional sloppy post-BJ kiss.

Main Event: B hiked up her nightshirt and lowered herself on my shaft. I lifted my hips up against B as she pushed down hard on me. I reached up and grabbed her breasts in both hands while she continued to press down. I got the hint — I moved my hands to her waist and slammed her straight down on my rod instead of the back-and-forth ride we usually share from that position, and kept slamming her down until I came.

Afterplay: B fell to my side but kept me inside her until I softened and slipped out. I cupped her ass with my hand until we both fell asleep. I woke a little bit later (with my hand still on her ass) and started to rub her until I felt goosebumps. My fingers drifted to teasing touches of her pussy, spreading our juices along her outer lips. When I started to stroke B’s taint, she clenched her legs before losing interest again.

I tried the “hook” maneuver but without touching B’s clit, then thrust two fingers inside her — that regained her interest. I added a third finger and plunged them in deep, and I could feel her squeeze her inner muscles against my invading hand. I added my thumb on her taint and my pinky on her wet clit — as I strummed my pinky across her clit, B clenched harder on my hand inside her. Finally I went for the big finish — pinky strumming regularly across her clit, 3 fingers pumping in and out of her pussy, and my thumb pressing into her pink rosebud. B came hard — all of her muscles throbbing — until she couldn’t stand the stimulation and pushed me away.

Afterglow: “I’m done — go away now.”

“Why do you keep touching me? I’m done!”

Rating: ★★★★

Second Night

Buildup: B was tired/buzzed enough after the New Year’s Eve party last night that she didn’t recollect my attempts to finish her off. I promised during the day that I would reenact the previous night’s play for her. B came to bed in her satin pajamas with the tiny hole between her legs, carrying a delicious drink made with eggnog and butterscotch schnapps. We were both tired from the jet lag and the partying and were under the covers by 10:30. I gave B some pre-foreplay by rubbing her feet with lavender massage oil as we sipped her decadent concoction.

Foreplay: I switched off the lights and B lay on her back with her legs slightly spread. I started by rubbing her inner thighs, up to the smooth areas along edge of her landing strip. I applied teasing soft touches along her pussy through the silky fabric until my fingers found the small hole there. I reached one finger in to touch her outer lips pressed together, then parted them to feel her wetness inside. Another finger joined in, and I pressed two inside her cunt as my thumb brushed against her clit hood from outside her PJ bottoms. B squirmed under my strokes then rolled to the side — my hard-on was pressing against the back of B’s legs and she shifted her hips to try to feel me behind her. I released my prick from my own pajamas through the fly and poked into her pajamas from behind as B strained to get release from my fingers.

Main Event: I flipped B the rest of the way over to her front and worked my cock through the hole in her pants — it was a tight fit. Inspired, I ripped the hole open wider with my fingers and B gasped at the sound of the tearing fabric. With more room to move, I plunged into her from behind — me sticking out through the fly of my pajama bottoms. I reached under the waistband of her pants to stimulate her clit — the position was just like the night before, but with more juices to lubricate B’s clit. She pushed back against me — just like the night before — and I pulled her up to her hands and knees and banged her hard — just like the night before. The only difference was the absence of the slap-slap-slap of our thighs, muffled by the pants we were each still wearing! The explosion of my orgasm wasn’t muffled, though.

Afterplay: After I came, I quickly replaced mmy dick with my hand and hooked her from behind (through the larger opening in her pants) — thumb in and finger on clit. It didn’t take long — she was ready and juicy and her clit was a little marble under my fingers. I
pressed rather than strummed until she came, then strummed tightly as her spasms subsided.

Afterglow: I remarked that this was probably literally the most fun you can have with your clothes on!

After-afterplay: We slept a little, then started playing again. I pulled B’s waistband down to her thighs — the only time all night that either of our pants came off — to find her clit still as hard and round as a marble. (It’s rare that B can take being rubbed twice in the same session.) I touched her with a spread hook — two fingers on her clit and my thumb reaching all the way to her taint, with no penetration, and the second time was also the charm.

After-afterglow: Restless sleep for both.

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: ★★★★

The Memory of Persistence

Buildup: It’s hard to stay horny during the end of year rush, so B and I didn’t have time to send any sexy chats and I never got any real feedback on the morning’s quickie. In fact, the only turn-on during the day was an online banner ad pointing to www.shaveeverywhere.com that I found amusing (having an “optical inch” myself.) By bedtime, B was complaining of a headache and was tired. She wore a sexy thin cotton camisole top, but bulky flannel sweatpants — a mixed message like the previous night.

Foreplay: B lay on her side away from me. I curled in next to her and placed my hand on the side of her breast, rubbing in very slow circles. Those circles got bigger and bigger until my fingers reached her nipple with no objection from B. Emboldened, I reached down to stroke her ass cheeks through the (ugh) flannel, then brought my hand up under her shirt and spread it so that I could touch her nipples simultaneously with my thumb and pinky. B’s breathing quickened slightly, and both of her nipples stiffened nicely. I reached back down to her ass, lowering her waistband enough to slip two fingers into her wet pussy. I ducked under the covers to remove her sweats and stayed to lick her belly near her hips. B had been enjoying my caresses silently to that point, but she said “oh, no you don’t” and pulled my shoulders to bring me on top of her — I stopped to lick her breasts on the way.

Main Event: B spread her legs wide as I mounted her, then brought her knees up high under my arms, digging her heels into my ass as I pumped. Nothing fancy — just straight missionary pounding, prolonged by my added stamina after the morning’s activities. I had to shift angles a little bit when my calves started cramping. The new angle brought me closer — it also did a trick for B and she coaxed me to my climax with insanely tight (almost painful) squeezes of her inner muscles.

Afterplay: B told me that she liked that, as I lay panting at her side. I reached across her chest with my left hand caressing her tit as my right hand tried to coax her clit to come out and play. B said, “I’m going to sleep” and I decided that I was tired enough not to mind.

Foreplay, part II: I drowsily felt a hand on my leg a little over an hour later — it was B’s turn to massage my thighs. I was still asleep, but dreaming of B’s hands stroking my balls until I was fully hard. I grabbed at B’s tits in my stupor before waking to realize it was no dream — B’s hands were all over me!

Encore: Awake and aware, I pulled B on top and she lowered herself on my hard shaft. She moved straight to the X position — I held her slightly sideways, with one hand on the front of her right hip and other reaching behind to play with her ass until she told me it was too much stimulation. B was working hard to find her orgasm, but we felt it slipping away. I flipped her over, and drove into her again and again from on top — feeling my own climax come close and then slip away as my legs cramped again (three times in a day isn’t so easy at this age!)

After-afterplay: B got up to pee (maybe that’s why she couldn’t come!) and quickly returned, lying on her back. My fingers went to work, circling and spreading her lips once again while teasing her clit hood. While I felt her button against my thumb, B spread her legs to give me better access. It took a while to find the right rhythm and combination of stimulation, but I was finally able to bring B to a strong climax (but surprisingly without the usual pulsation around my fingers — only one hard clench as she came.)

Afterglow: B confessed in the morning that she wasn’t able to fall asleep without coming, and thanked me for my persistence. We talked about the complete role reversal — this time she was the one to arouse me out of a deep sleep, and I was the one to respond, enjoy the act, try to come myself, but still not quite “get on the board” to ride my wave.

Rating: ★★★★

Olive You, Two

[With this post, I am caught up to real time sex -- depending whether or not I score tonight -- for the first time in literally months!]

Buildup: B didn’t have a meeting on the calendar, but her friend invited her to a get-together with martinis afterward. Before I could complain, B pointed out, “You like it when I have olives” — hard to argue with that! Having just written about our last time and realizing B had been on top a lot lately, I made a promise to myself to drive the action. When B got home, she changed into a purple cotton nightie — not explicitly sexy, but there was something very fetching about the way she stood in the doorway and her silhouette with the bathroom light behind her.

Foreplay: We started by kissing, and I tried to set the tone by reaching for B’s tits. She pushed my hand away — it’s getting near her period and her nipples get too sensitive. Instead, B moved to me and pulled up my shirt so she could run her hands over my chest and my own sensitive — but not too sensitive — nipples. (OK, I thought, but I’m still gonna be on top!) As she licked my nipples, B’s hand wandered down to my shorts and she began to squeeze my shaft. I was still a little soft — maybe from having been shut down from feeling her up before? But when B moved her hands around my waist and came up from beneath my legs, cupping my balls along the way, I was as I hard as expected. B pulled my erection through my fly and played with it with her hands, then impatiently pulled my boxers down. As I kicked the shorts off of my ankles and spread my legs, B leaned over and began sucking just the head of my dick. I reached behind her and moved my arm so that I could massage her ass while she blew me — when I slid three fingers along her crack, she bobbed her head up and down my full length. With spit as lube, she took her thumb and forefinger in a tight ring and started stroking in the same rhythm as her lips moved up and down my cock. (I had told her last week during a discussion of how her jaw got tired that it’s not cheating to use your hands — she took the hint!) When she needed a rest or to catch her breath, she kept a steady stroking pattern with her fingers — I was concentrating hard to keep from exploding. I distracted myself by playing more intently with B’s ass cheeks, but that distracted her and she broke off the blowjob with a very wet, very sloppy kiss.

But she didn’t stop stroking me.

Our tongues thrashed, while she continued moving her tight hand up and down my shaft (now a full fist instead of the tight ring.) I began to panic — I was going to come in a matter of seconds if she didn’t stop, but there was a tight, wet, pussy right there still waiting to be ravaged!

Main Event: Fortunately, B stopped her handjob just in time and lay back on her side of the bed. I was still close to the edge, so I wanted to start slowly. I knelt in front of B and spread her legs wide, massaging her vulva with my hand before pointing my prick inside her. I moved in and out slowly, still using the palm of my hand on her inner thighs and over her mound — probing her clit with my thumb as I thrust. B’s boobs were bouncing invitingly each time I pushed into her, so I took both hands and grabbed on to them instead. B fetchingly grabbed the pillow behind her head. I was impressed with how long I was able to last (given how close I was to finishing before I started) but B had the look on her face that told me she wanted to be taken. I stretched my legs out behind me and sank in between B’s legs — which she lifted and wrapped around my waist. After a few strokes there, I leaned forward, putting all of my weight into my thrusts and pressing B against the mattress. She squeezed me delightfully and I came, HARD. I stayed in, grinding against her pubic bone, as my cock twitched with the remainder of my come.

Afterplay: I slipped out, slipping my thumb in, but B grunted and indicated she wasn’t interested (it seems to be true many times after a martini meeting — wonder why.) I was exhausted, too, and didn’t mind falling asleep.

Encore: I woke less than half an hour later and rolled from my side (facing away from B) to my back — so that we lay thigh-to-thigh. Although she pushed my hand away earlier, this time B rested her hand on my thigh — sproing! — and didn’t complain when I put my hand on her thigh. I quickly started smearing her juices around her pussy, across her clit hood and her very swollen outer labia, bringing sighs. I penetrated her with two fingers and she spread her legs wantonly. As I shifted to my side to get a better angle to finger her, she was shifting her hips to get closer to mine — I was fully hard again. Finally we aligned ourselves so that I entered her from the side, underneath her, as her leg crossed over my waist. She let out a sexy “Ohhhh” as I filled her from this new angle. As I fucked her from under her legs, I reached over her thigh and rubbed her clit with my right hand. Her soft moans let me know she was enjoying it, but I could sense she wasn’t “climbing on the board” to ride the wave.

B moved to her side away from me and I followed, taking her by the waist and continuing to turn her until she was on her knees. I took her doggy-style in a half-straddle, then spread my legs to straddle her hips. Like the last time in this position, I bottomed out a couple times before finding the right angle and depth. I shifted hands, trying to find the best angle to reach beneath B and fondle her clit while I filled her from behind. I thought I had found it — I held my dick still inside her walls, and bounced my fingertip in a steady beat against her swollen clit. B clenched tightly in a matching rhythm, trying to get off, but her angle and the effects of my second effort meant that I was softening, and the tighter she clamped down, the closer I came to slipping out. I had to get hard for her again even if it meant losing the rhythm, and I banged into her ass quickly. Her climax was fading from view after multiple attempts to find it, so I pulled up, pulled my legs between hers, grabbed her ass in two fists, and pounded into her, my thighs slapping against hers and my balls swinging into her. For an encore, my orgasm was awfully powerful.

After-Afterplay: I still wan’t ready to give up, trying various hook permutations — but although B’s sighs indicated pleasure, she wasn’t able to finish and finally told me it was OK to give up.

Afterglow: Exhausted sleep yet again.

Rating: ★★★★ (would have been an easy ★★★★★ if I could’ve made B come!)

Long Time Comin’

Buildup: A very long intersex gap — among the longest (when we were in the same place) since I started the diary. Sometimes too tired, sometimes fighting, sometimes both. In the meantime I had been posting entries from a couple weeks back, all of which had me on top, so I was thinking about being topped — not remembering that’s exactly how the last time went! We thought that Sunday night would break our drought with B’s offer of a massage after my game, but she was asleep when I came home. Today we fought again, but after my second game in as many nights B offered a backrub again. She came to bed with her favorite dark beer and signs looked good — I put on my lucky PJ bottoms. B lightly scratched my back while watching the end of a stupid TV show, then had me lying face-first on top of the comforter, pointing towards the foot of the bed. She finished the show with a rather vigorous massage of my ass through my pajamas — arousing more than my hopes — but she came to bed in a virginal ankle-length cotton sleepshirt. She may have felt the part, but she didn’t look it.

Foreplay: In spite of the lack of erotic lingerie, B still showed signs of lust. She went from scratching my back to a deeper massage, using our favorite lavender massage oil. I had switched channels to the football game while she was in the bathroom, and I made a point of watching Chicago drive down the field, even as B was driving my pants down my thighs. Her hands moved from my shoulders to my lower back to my ass — rubbing just as vigorously as she had before. When she moved to my ankles to pull my pants off completely, it was time to turn Monday Night Football off.

I stayed on top of the covers and B rubbed her way back up my legs, between my thighs, then directly to my taint. I pressed myself against the bed to see where she’d go next — she kept her finger right next to, but not quite on, my ass, and rubbed steadily. I heard her pour more massage oil onto her other hand, which she briefly ran over my ass cheeks before wedging it under my hip to stroke my cock from the front. I made no attempt to resist and raised my hips off of the bed — B ever-so-slowly ran her firm grip along my shaft like the night of her reacharound handjob. She stroked me slowly and steadily (but I didn’t want to come like that!)

Main Event: Just then B turned me over — my head at the foot of bed, still on top of the covers. She hiked her sleepshirt up around her hips and lowered herself onto my straining prick. I pushed my hips up against her as B turned slightly sideways — leaning forward with her right arm over my shoulder, but with her left arm at my side. I held my hands above my head at the edge of the bed and let her have her way with me. When she fell forward, with both arms above my shoulders, I reached to hold her hands in mine. B rode me with a steady, solid rhythm, and I broke the grip on her hands so I could run mine up her side and along the sides of her breasts. I started groaning with impending orgasm — I could feel myself come long before I actually ejaculated. B fell forward and lay on me with her head next to mine on the pillow as I twitched inside her.

Afterplay: We moved to our proper orientation on the bed and got under the covers. B was still in her long shirt, so I pulled the hem up to expose her buns. “What are you doing?” she asked. I let her rest for a moment while I simply lay my hand on her ass, then fell asleep myself. A little voice reminded me she hadn’t come and I woke, remembering to run my hand along her ass cheeks and inner thigh like last week. I moved my right hand under the covers to slide inside B’s wet lips, then went to the hook — thumb in her slit, finger on her clit. Her clit was still hiding, so I added my left hand pulling at her perineum from behind and worked my thumb out until it only teased the entrance to her pussy lips. When I could feel her nub harden, I went to a classic one-handed hook — my thumb flat on her asshole while two fingers toggled her clit. B began to gasp and throbbed on my hand — I gave her clit a quick hard strum and she throbbed twice, I strummed again and she convulsed again. Finally she was too ticklish and squirmed away as I squeezed her thighs.

Afterglow: I had a “hot flash” so I sat up and watched the end of the football game, then rubbed B’s nipple and boob through her sleepshirt (with no reaction) until I was ready to fall asleep.

Rating: ★★★★

Brilliant Disguise

Buildup: B had gotten her hair styled (she called afterward, telling me she looked like a completely different person) and she had plans to go out for a drink with her friends after a meeting — she pointed out early in the day that those were usually good signs for me getting laid. Later in the day, she called again to remove all doubt by confirming our date. I played on her “different person” comment from before and asked, “How will I recognize you?”

“I’ll be the one who’s wet for you.”

Oh. Hard to argue with that.

Foreplay: The meeting ran late and I was already in bed with the mood light on when B came home — tipsy, sexy, and silly. She really did look different. She kept grabbing at my crotch through the covers of the bed but wouldn’t let me touch her back, so I put my hands over my head on the pillow in a submissive pose. B came to bed naked (her hair looked different but I recognized that body!) She started with her hands on my chest, followed by her lips. As she licked my sensitive nipples, her hands roamed along my chest, belly and legs, but she carefully avoided touching my raging hard-on. She spread my legs wide apart by pushing on my thighs, then ran her hand over my pajama bottoms along my inner thighs, under my thighs, and up my ass crack. She still hadn’t touched my dick.

When she finally did, it was to fish my shaft through my fly so she could suck it. She gave me a deep, strong blowjob, pulling me into her mouth with her hand under my ass. Through the flannel, her fingers were tickling my asshole, making my dick throb and jerk in her mouth — she knew what she was doing! I wondered if she was going to finish me off there, when she broke contact for the classic sloppy post-BJ kiss as I kicked my pants off.

Main Event: B mounted me from on top — I slid in immediately and raised my hips high off the bed. B rode me so forcefully that I slipped out once — I brought my hands down from over my head and ran them along B’s side, using my thumbs to brush against her stiff nipples. Surprisingly, she asked me to stop, and she placed her hands on my chest while grinding hard against my shaft with her full weight. “You’re gonna make me come,” I warned, but that just encouraged her to grind harder and longer — I exploded inside her.

Afterplay: B was too tipsy to continue — before I could begin to touch her, she was already saying “Shhh” and “Go to sleep.”

Afterglow: Tried to sleep through sounds of moving air: B snoring next to me, gusts of wind blowing against the house, heat rushing through the registers from the furnace, and an airplane flying overhead.

Rating: ★★★★

Play Ball(s)

Buildup: We were on a new roll, and spent much of the day stealing little make-out sessions and dropping suggestive hints. Friends of mine were having a holiday party, and I offered to pull off at my exit instead for a quickie in my office. B didn’t decline, but said she’d rather have a drink or two to relax first, so we headed on to the party (where we had enough fun that we stayed through our window of office opportunity.) The horniness didn’t subside, though, and B offered to scratch my back as she read at bedtime. When she finished, I fell back against the pillows in an extra-sleepy, almost trance state.

Foreplay: She says I started it: she could feel my hard-on throb and twitch against her arm when she cuddled in against me under the covers. I say she started it when she reached over the erection and ran her hands down the back of my boxers to lightly scratch with her fingernails (the hard-on was going to be there any night she lay next to me!) B’s fingers tickled my taint through the boxers and she ran her hands along the V of my thighs, beneath my scrotum. As I lay there, she started to rub my shaft slowly with two hands through my fly, then used one hand to play with my balls. She worked my shorts off — struggling to get them over my strong erection — then went down on me, sucking long and deep while using her free hand to energetically tease my sack. I didn’t make a move to guide her and kept my hands to myself while she blew me. B’s fingers moved daringly along my perineum and when she touched my asshole, I groaned deeply. The groan told B to move to the next phase — she skipped the usual sloppy post-blowjob kiss and instead pulled down her pants and pulled me on top of her.

Main Event: I put a hand under B’s back and pointed my rock-hard rod between her pussy lips. B pulled her legs up high and I held her knees under my arms. I thrust into her — deep and hard and strong — then B reached below her ass to stimulate my scrotum. She used her fingers to tickle, strum and swat my balls as I continued to pump into her — the sensation was like heaven. I was groaning continuously as I thrust — pumping long with the stamina that comes from frequent sex and the delightful distraction of her ministrations on my balls. When I came, it was loud and hard.

Afterplay: I caught my breath laying at B’s side — I brought my fingers between B’s legs, only to have her intercept them with her own. She was too sleepy to come, so we quietly held hands.

Afterglow: We fell into a deep sleep; I had a dull ache in my balls the next morning from the rough handling, but the orgasm was so intense I would do it again!

Rating: ★★★★

Still “Wet”

Buildup: We were both still glowing about the previous night (though B warned me against “Monday morning quarterbacking — she’d rather do than talk.) On the other hand, over lunch she had very kind words for my endowment relative to (most) lovers past. She had borrowed some sexy bedtime reading, “Rapture” by Susan Minot, which describes a single blowjob from the point of view of both parties. Given the potential, I though the book sucked (so to speak.)

Foreplay: B had fallen asleep in white silk PJs as I finished the book — turned away from me. When I turned out the light, I began running my hands along her body over the silk — from her legs to her torso, back down to her butt, her inner thighs between her legs, and back to her chest, this time under the shirt. I reached beneath her top to fondle her boobs and B moved her arms to give me room. My hands worked back down to press on her pussy through the pajama bottoms, at the same time as I pressed my erection against her ass though the silk. I slid my hand underneath her waistband and got one finger wet — I pulled her pants halfway down and got two fingers wet, which I used to spread on her erect nipples. I pulled her pants off completely and teased her ass with my cock head poking out through my fly, then pulled my pants off as well.

Main Event: I ran the tip of my dick down the crack of B’s ass, then pushed it to the edge of her pussy. I held it in my fist and ran it around her lips without slipping inside yet — I was still a little soft after the anti-climactic climax of the book (again, so to speak.) Finally I slipped in from behind, both of us on our sides — B’s pussy was very slick from the foreplay. I rolled her to her stomach and B pulled the body pillow beneath her to straddle, as I stradded her right leg. With my left hand, I reached to cup her breast, then brought my hand between her legs to touch her clit. B clenched hard on my dick and was rolling back and forth, feeling me penetrate her from different angles. I could feel her getting close, and I switched from holding my dick still inside her to stroking into her — with each thrust, she sighed and moaned into her pillow. I spread my left leg so that I was straddling her legs with mine and switched hands to rub her clit with my right. I stroked slowly and B began bucking and rolling against me again.

“Can you feel that?” B asked as she came and her pussy spasmed against my dick inside. “Yes,” I growled in her ear from over her shoulder. I pumped again while straddling her legs, then pulled up and out to put my legs between hers. I pulled her up to her knees and entered her again. I pounded her doggy-style, my erection fully restored, and listened to my thighs slapping into the back of hers as I finally came.

Afterplay: None.

Afterglow: B commented, “We’ve never done that before”, referring to her coming from my hand while I was inside. Clearly she hasn’t been reading this diary! I pointed out that we had, just before my last trip.

Rating: ★★★★

Sunshine Daydream

Buildup: Continuing the Grateful Dead analogies to our sex life: the song “Sugar Magnolia” on record is actually two songs together — “Sugar Magnolia” and “Sunshine Daydream”. On occasion in concert, the Dead would play the Sugar Magnolia section early in the set, but not play the Sunshine Daydream part until the end — at least once in the 90’s, the Sugar Mag and SSDD sections were separated across several shows!

The point being: our nooner was like the Sugar Magnolia section, but B was waiting for the Sunshine Daydream closer that night. I wasn’t quite sure if I had more in me, and when B finally came to bed she was wearing a turtleneck and boxers shorts — not exactly an inviting look. B fell asleep early and went downstairs to watch a Tivoed TV show. I came back to bed and scratched B’s back lightly, then traced the underside of her breast with my finger.

Foreplay: B didn’t realize I had left already. She asked, “Are you back?” I mumbled yes –

– and then she attacked me!

Even half-asleep, she went straight for my chest, sucking on both nipples, then ducked under the covers and brought her lips down hard on my cock, which had sprung to attention. I pulled the covers over my head to make a tent for B to move around. She got up on her hands and knees and moved forward to that her boobs fell to each side of my shaft — I oblingly pushed them together, mashing her nipples, as we engaged in an upside-down titfuck. While I was thrusting between B’s boobs, I brought my knee up against her mound and felt her press against it.

Main Event: When I let go of B’s tits, she rolled to her side and pulled me on top. I was surprisingly hard, given that I hadn’t expected we would have sex after all, but had unsurprising stamina, given the nooner that day and two encore sessions earlier in the week. B’s legs were spread high in the air and I was holding her ass off the bed with both hands. With each stroke, B grunted “Oh my God, Oh my God.” I bent down to lick each of her boobs in turn, then pulled a pillow under her ass to keep it propped up. I can’t resist that look, and dove down between B’s legs to get a taste of her pussy, but she wasn’t having any of it — she wanted me back on top, driving harder into her. If possible, she brought her legs up even higher, and I followed by thrusting harder and deeper, putting my full weight into each stroke. I let her know I was going to come even before I felt it — B answered with powerful squeezes of her inner muscles like a vise on my cock until my semen shot forth.

Afterplay: I had my encore for the day, but B still hadn’t come. I put my hand over her pussy while I was still on top, but B brushed it away. I lay to her side while she stayed on her back, and tried the same extra-light touches that had worked the previous session. She squeezed her legs together briefly, then fell back to sleep. I was still turned on, and I played with her tits through her shirt — marvelling at how they made a perfect, full, just-more-than-a-handful, and feeling her firm nipples poking into my palms. I tried again to finger her — this time reaching beneath with my left hand and probing her from below. Again she brushed me away, and turned to her side facing away from me.

It would seem that turning away would be a rejection, but in our bed (and B’s physiology) it’s an invitation. I worked my thumb between her lips and let my long middle finger ride up her labia to settle on her nub hiding at the peak. B quickly clenched down and squeezed her legs together as her clit hardened under my touch. When she started a rhythm, I let my thumb slide out of her pussy and rest on her taint, making tiny circles. She squeezed more and more frequently, getting closer, closer, closer — then she held my hand against her clit with her own hand and I felt her pussy throb, throb, throb, as she finally came.

Afterglow: B thanked me for getting her off, but asked, “Don’t you get bored?”

Rating: ★★★★