Sinful Sunday: Two Pairs
Jack slid my blouse and my bra over my shoulders, freeing my breasts. He leaned down to suck one of them, beckoning our friend over to have a taste of the other. After a few glorious moments with two mouths on my nipples, he stopped, and suggested that he and I have some fun with her instead. He threw off her top, and I unhooked her bra. While I stroked and kissed her magnificent breasts, he kissed her neck and her shoulders. My hands wrapped around her body, kneading her soft, supple ass with eager fingers.
We moved her to the bed and began to caress her through her remaining articles of clothing. Then Jack turned her onto her back, and as I kissed and touched her, he stripped her to her sheer black panties. He climbed onto the bed and we ensconced her between our bodies, our mouths traveling along her sweet flesh as our fingers came together inside her. We had fun tantalizing her warm, wet pussy, but it wasn’t long before the panties simply had to go. As I undressed I looked up and saw Jack stepping out of his boxers.
He settled between her legs and began to devour her. I was really turned on as I watched him lick her lips and suck her clit, knowing the overwhelming sensations of pleasure she was experiencing. And while I wish I could remember every lick, every stroke, every orgasm that happened over the next two and a half hours, the simple fact is that for a number of reasons including a pervading air of unbearable excitement, threesomes are often a blur once they’re over.
However, I do vividly and fondly recall a number of hot details from that evening: Kissing our friend on the lips for the first time, tasting her tongue against my own. Jack fingering her and then bringing his hand up to my mouth so I could enjoy a taste. Our friend brushing the hair out of my eyes as I sucked her breasts. She and I sucking Jack’s cock together. Watching her legs wrap around his head as his skilled tongue brought her to a powerful climax. The wonderful, intense sounds she made as she came.
We even got a picture, hence the title of this post.
Formspring Friday: Sexual Healing
Jill- you’ve spoken more than once of your abusive past. What is it about JACK that has enabled you to heal in ways you couldn’t on your own? I’m sure you did a certain amount of work on your own. All survivors must, but what about Jack?
The Naughty Hangout: Click!
Here’s Jill with my Canon PowerShot Pro. I’ve had it since 2004, and it’s accompanied us on virtually every vacation we’ve taken together. This camera has photographed the Grand Canyon, Blarney Castle, Mendenhall Glacier, Hollywood Boulevard, Times Square, Space Needle, and Red Rocks Amphitheatre, among other noteworthy places.
Wicked Wednesday: Election Night
We’d been planning it for weeks.
Actually, that’s not true. It had been months. It was in summer – our anniversary, to be precise – that she sent us a message to let us know she’d be coming out to San Francisco in November and ask if we’d be interested in getting together. We were pleased by her inquiry, so much so that we took a break from toasting to our marriage and wrote back to let her know that, yes, we were definitely interested.
Three weeks ago she wrote again, this time to give us her itinerary. We had already arranged to have my parents look after our daughter for a couple days during her visit. Leaving our child with a babysitter is always dicey. Typically the relatives we trust to look after her are unable or unwilling to watch her past eleven PM or midnight, and while this is helpful on those occasions when we want to meet friends for drinks or perhaps see a movie, we had no intention of rushing through our evening. So the fact that my parents were able to take her for as long as they did was quite serendipitous.
She told us that she could meet on Tuesday or Thursday evening, though Tuesday was preferable. Of course, Tuesday was Election Day in the United States, and a flurry of thoughts ran through our heads. We tend to follow election coverage pretty closely, moreso during a Presidential election year. And while we were certainly excited by the prospect of finally getting together, we weren’t sure how this very important election might affect our plans for the evening. Obviously we didn’t mind skipping the Election Night coverage for once. Also, the overall stakes of the election had us pretty stressed out. It would be nice, we agreed, to distract ourselves with a little adult fun.
On Tuesday night we drove out of our suburban paradise and headed up to the City. The traffic was considerable as expected, but we listened to the news on the way, and it kept us optimistic. We met her outside of the bar in her hotel; she wore a black dress, boots, and a red sweater. We’d admired her for months, quite openly, on her blog and on Twitter, but neither Jill nor I were prepared for just how stunning she was in person. The first thoughts that crossed our minds did not involve dinner or even drinks, but rather taking this beautiful woman upstairs, stripping her clothes off of her, and having our way with her before letting her have her way with us.
It had been a long day, however, and we were all hungry. After perusing the menu at the hotel restaurant, we decided to take a walk. We settled on a nearby spot called John’s Grill, tempted by its promise of 63 Cocktails. Once inside, we found a mere ten cocktails on offer – actually nine, since the one I selected was unavailable – and the waiter explained that the number 63 is the restaurant’s address on Ellis Street. Despite the misleading come-on, the food was good.
As we waited for our dinner, we discussed politics among other topics, and it occurred to us that given the importance of the election our evening would have been much different had our dining companion been a staunch Republican. In the middle of our meal, as I tried to check election results on my phone, a friend texted me that Obama had won. I confirmed it, and we all exhaled. The stress lifted. We had one thing and one thing only on which to focus for the rest of the evening, and it didn’t involve politics. Or clothes.
We found ourselves in her hotel room, sitting across from her on the sofa while eyeing the comfortable king-size bed not far away. I started by releasing Jill’s breasts from her top, doing my best to distract the two women from their conversation. It worked, naturally. I asked her if she’d like to have a taste of one of Jill’s nipples, but quickly retracted the offer. No, I didn’t want to keep both for myself, though it was tempting. Rather, I was preoccupied with thoughts of Jill and I spoiling our lovely new friend instead.
I stood behind her, nuzzling her neck, as Jill kissed and caressed her from the front. It didn’t take long at all before I began to undress her, revealing first the sexy black and white bra featured in her Twitter avatar, and then the full and tantalizing breasts we’d seen so often in her online self-portraiture. They stood close, pressing their breasts together and noting similarities between their respective pairs. My hand settled between her thighs as Jill began to lick and suck her nipples. Eventually I suggested that we move things to the bed. She and Jill lay on the bedspread as I removed the rest of her clothes. Jill was next to undress, and then I.
We lay naked together, Jill and I each sucking one breast as our hands traversed her fine figure. Her arousal was evident as we parted the lips of her pussy. Our fingers worked together, circling her clit and feeling her orgasm build. But I needed a taste, and I kissed my way along her body before settling between her legs and devouring. As Jill continued to work on her breasts, I lapped as though I’d never tasted a woman before, and sated myself on her sweetness.
The exquisite debauchery that followed was eventually cut short by our friend’s need for an early start the following morning, as well as our need to claim our car from the garage before it closed at midnight. As Jill and I took our leave, it occurred to us that we never would have predicted that our candidate’s victory would be only the second greatest part of Election Night.
Retro HNT: Crescendo
TMI Tuesday: November 6, 2012 – Movember
2. The say ‘putting on the beared’ means going down on a lady with a full bush. Do you prefer a bearded, trimmed or bald pussy?
Putting on the beard, huh? I can honestly say that I’ve never heard that expression. Normally when I want to refer to going down on someone, I simply say “going down”. In the event that my meaning can be misconstrued for, say, use of an elevator, I have been known to favor the less ambiguous “eating pussy”. I’ve never been a fan of “eating out”, because it sounds too much like going to a restaurant for dinner. Anyway, I hate to say that my preference is to go down on a completely-shaven pussy, because I fear that it makes me sound shallow. It’s not an issue of taste or even of cleanliness; it’s simply easier. I strive to do a good job where oral sex is concerned, and it’s a bit easier when some gardening has occurred.
3. What’s your preferred style of ‘tashing on’? (snogging)
This question came close to breaking my brain. While I’ve heard the expression “snogging”, “tashing on” was a new one for me. I did a Google search, which returned among other results the following, from Urban Dictionary: “Local Geordie dialogue for getting off with, ‘pulling’ or ‘Snogging’ with another person”. Needless to say this didn’t clarify anything. I understood “snogging” to mean kissing, but decided to do a search in order to not sound completely out of my depth. One site likened the term to what others call “making out”, i.e. kissing, caressing, fondling, etc. So essentially this question seems to be asking for my favorite way to make out. I wanted to give an answer along the lines of “while bending Jill over the sofa and fucking her from behind”. While I do enjoy this sort of makeout session, it’s not my favorite. I tend to prefer one of those ridiculously-sexy standing-up-face-to-face snogs, complete with hands fumbling at belt buckles and shirt buttons.
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Mounted Monday
Sinful Sunday: Happy Halloween!
…here is Jack in his scary ghost costume…
Formspring Friday: Fisting Fiesta!
How did you get into fisting?
(Submitted by Cougar in Training)
Jack’s Answer
I’m fairly certain that the first time I fisted someone was around age twenty-one or twenty-two. The woman was a casual fuckbuddy who sustained me through a couple otherwise dry spells during my twenties. During a long and very exciting session of foreplay one evening we found ourselves naked and making out on her bed. She was playing with my nipples while I fingered her pussy. I’d slipped two fingers in, but she wanted more. Soon I had four fingers inside her, my thumb rotating slowly on her clit. Then she asked me, somewhat awkwardly as I recall, to give her my thumb, too. I was aware of fisting, though I’m pretty sure I regarded it as the stuff of urban legend; still, I did as I was asked.
I didn’t get my hand all the way inside her, i.e. all the way to my wrist, but for all intents and purposes my entire fist made it in. Having already found her G-spot I resumed stimulating it. She climaxed almost immediately, her intense moans during the buildup the perfect encouragement for me. When she drenched my hand and my arm I was fascinated. I’d found a couple G-spots in my life, and I’d made a lot of women very wet in doing so. But nothing like this! When I’d seen women squirt in porn I wasn’t sure whether it was some sort of camera trickery, or a talent only a small number of women possessed. And now I’d made it happen!
Being a geek, I’d read up extensively on female sexual response and was aware of the debate over whether female ejaculate was urine or something else altogether. I was pleased to learn that it wasn’t urine. She, on the other hand, was mortified. She apologized profusely, insisted that she’d never done that before, and hurried to get me a towel. I did my best to assure her that she had nothing to worry about and that I was in fact totally turned on by it. It didn’t help. Continuing to apologize, she tried to clean me off, not that I necessarily wanted her to. At this point I’m pretty sure she was near tears, and I went into full-on aftecare mode. I suggested that we take a shower together, and as we huddled close under the water she relaxed a bit. I told her how exciting it was for me, and she admitted that it was the hardest she’d ever cum in her life. Still, I’m not sure that I ever fisted her again.
Jill’s Answer
Jack was the first person to ever fist me. He found my G-spot pretty early into our sexual relationship, and I loved the sensation. It led to very intense orgasms and always resulted in me squirting. As we continued to experiment with G-spot play, Jack would put more fingers inside me at my urging. The first time it happened he was stimulating my G-spot with two fingers and my clit with his thumb. I asked for more fingers, and he put in the other two, and continued to use his thumb on my clit. Eventually he took his thumb off my clit and replaced it with his very eager tongue. As he licked me, I could feel him slip all five fingers inside me. I felt so full, and I knew my orgasm was near.
I loved feeling his fingers undulate against my G-spot at the same time that his tongue danced over my clit. I knew I was going to cum very quickly, but I wasn’t prepared for just how quickly it happened, and for that matter how intense the orgasm was. I’d never felt anything like this before. My orgasm was earth-shaking, definitely the most profound I’d ever had. My ejaculation was torrential as well, and I soaked Jack’s face, chest, and hand with my juices. I wasn’t expecting it, and I worried that he was going to be turned off by what I had done, but he didn’t even slow down. It was very enjoyable, almost too enjoyable. Definitely not something I was used to experiencing.
G-spot orgasms are my absolute favorite kind, but I can’t always handle them, and sometimes I actually cry from the intensity. I have to be in the right frame of mind in order to relax and get the most out of them. If I can do that, it makes it much easier to allow Jack’s fist all the way in. Of course, I suspect that Jack loves fisting me even more than I love being fisted (which is saying a lot), and sometimes he’ll pull it out as a party trick when we are camming or performing for a live audience.
We’re down to our last sexy question and we need more if we’re going to keep Formspring Friday going! If you’ve got one to ask, please drop us a line on Formspring, or use the handy Formspring widget on the right-hand side of our blog. (While you’re at it, be sure to check out Cougar in Training, and thank her for consistently providing such awesome questions!) To see who else participated in Formspring Friday this week, search #FormspringFriday on Twitter! If you have a Formspring account and you aren’t already participating, feel free to join in the fun!

















