Steve's First Night Out

When we first started "playing", Monica and I were unsure where we were going to stand on the same room / separate room decision. Monica was leaning towards same room while I was leaning towards separate room but no final decision had been made.  At that time we were thinking that primarily our activities would be limited to swapping with other couples and the question seemed pretty obvious.


Fast forward to now and what we have found is that finding couples with whom to swap is hard but finding singles interested in one or both of us is, relatively, easy.  So our questions and decisions are now being made from a very different perspective than the one we originally imagined.


If you have been reading the blog, you will be aware that we have been heading down the "play alone" path for some time ever since Monica began meeting guys ahead of our play sessions to give them head in anticipation of the "main event."  A few weeks ago I finally got the chance for my own playing alone fun.


It was with my friend that I met online in "A Surprise Meeting", we had put our playing on hold for the holidays but we were both available now and Monica was able to stay home with the kids so that I could go out and play.


We made our plans quickly, I rented a hotel room near where she lives a town over, and headed over there around ten after the kids had gone to bed for the night.  I picked up a six pack of beer just in case it was needed but left it in the car assuming that I would not want to have it with me.  I also grabbed a Monster as I have been completely exhausted as of late and have energy for tonight's sessions is going to be tough.


My "date" arrived late having gotten lost trying to find the hotel.  I had a book with me so I was happily reading while I was waiting.  Not a big deal.


My friend came in the door and it was knock knock, "Hey, good to see you again.".... kissing standing at the foot of the bed.  No time wasted there.  I assure you I was ready for small talk but she jumped straight to tongue action and in under twenty seconds was stripping down ready to get it on.  She left nothing for me to do, her clothes were on the floor in a flash and she was climbing in to bed.


So I got undressed and joined her in the bed.  She turned on the television, I guess for background noise but with the talk shows that she was selecting it was a bit disconcerting as the television was so close to us.  Not nearly as good as having porn on, that is for sure.


It only took a minute of sucking our her firm double D tits before my right hand slid down her stomach, spread her legs and was pushing a finger or two into her very wet and very ready pussy.  Her pussy was shaved and eager.  It was only a minute more before her first orgasm.  It has been a long time since I was last with someone who comes so quickly and easily.  Monica is not multi-orgasmic so I have adapted to that mode of sex which involved a long buildup and eventually a single, hopefully massive, orgasm that lasts and lasts when done right.  But the orgasms tonight were fast and frequent.


Throughout the evening she probably came around twenty times.  My record was making a girl come thirty-four times but that was set in around 1997 with an eighteen year old blonde that I had practice with and she only had to stop from exhaustion (hers, not mine.)  It is a nice change of pace to have the rapid orgasm experience again.


And, like the blonde girl that I so adeptly pleasured all those years ago, tonight's playmate was a squirter.  Now Monica is jealous.  She has always wanted to play with a squirter and thinks that it is so hot that I had one fifteen years ago and she has been looking for one for a long time now.  And now that I am playing with one, Monica isn't here.  It will happen eventually, but she has been wanting to try it for so long now.


The squirting was not all that intense, it was just a little bit.  My old squirting partner from the late 90s was a real pro which is hot and sexy but really messy and difficult to manage when you can't avoid it.  But I'll cover that another time.  


We had a nice time.  For a women with a kid in her early forties her body was firm and her breasts were ample.  She was actually taller than me as well, just by a little bit, and I am no short.  I'm definitely not tall, but average for a guy.


The sex was good.  I made her come from fingering her over and over and then about three times when I went down and ate her pussy.  Monica will attest to the fact that my pussy licking skills have taken a leap forward in the last few weeks.  Some recent stylistic changes and yielded impressive results so it was nice to get to test these out on a very willing new subject.


It was not a late night.  Probably two hours of sex, tops.  Once she had come... a lot, I donned my condom and put her on her hands and knees on the side of the bed so that I could stand on the floor beside the bed and penetrate her doggie style - one of my favorite positions.


Sliding my cock into her waiting, black pussy lead me to discover how small her pussy was.  And I don't mean tight, it was probably average in that regards, but it was hard to fit my cock into her as her pussy interior was small and somewhat shallow.  I had to work to squeeze myself in but she enjoyed it and soon I was pounding away on her.


She came once while I was pounding against her little black ass and then when I came the force of my orgasm sent her over edge into a thrashing orgasm of her own.  Unfortunately she lost control of her back muscles and buckled which made it impossible for me to remain inside of her as she changed the entry angle so dramatically and squeezed me out as well with her pussy muscles.


We took a bit of a breather and talked for maybe an hour.  Then she asked me to make her cum another four or five times.  We called it a night and I got dressed.  She wanted to stay and use the hotel, which I thought was rather odd as she meant staying in bed and watching television not showering and getting cleaned up, but whatever, we have the hotel might as well get use out of it I suppose.  After I was dressed and getting ready to head out the door she grabbed my hand and slid it down under the covers and asked me to get her off one last time before I left, which I did.


And that concludes my first time playing alone.  The first of many such episodes, I hope.  This also was my first time having sex with a black women.  And my first time having sex with someone older than myself.  An adventurous night.


I got home and filled Monica in on the details.  It was really late and we were tired so we fooled around for a bit in bed but didn't have sex.  We saved that for the next day.


Now that both of us have managed to play alone... we can count the experiment as a success.  - Steve

Monica's First Night Out

Tyler and I had a lot of fun together during our car meeting, and during our 3some, so we've decided that he will be a regular for as long as it suits us both.  We thought it would be fun to meet just the two of us, so Tyler invited me over to his place.  I dressed in my black thigh-high suede boots, a black lace thong, a lace zebra print bra and a short, low-cut dress (This would later become my go-to seduction outfit, lol).  When I arrived, Tyler met me in his parking garage and walked me to his apartment.  He had just worked out, so he got me settled on his couch with the T.V. remote while he showered.  When he was done, he came out and took another look at me, then asked me to stand up and turn around so that he could get a better view of my outfit.  With a "Wow, you look sexy!" he invited me to sit down next to him again and we started making out.  He told me that I looked so good he almost didn't want to undress me, but then lifted my dress over my head to grant him better access to my breasts.  My bra came off next so that he could suck on my nipples hard, the way I like it, but when he began fingering me, my panties stayed on (Tyler has a thing for panties, and likes to play with them on for as long as possible).  We made out for at least an hour with him fully clothed and me in just my panties and tall boots, which made me feel oh so naughty and very hot.  At some point, Tyler pulled me on top of him so that I was straddling him while we kissed.  He began kissing my neck and it felt so good, that I was surprised when he pulled back, looked down and said "Oh shit, Steve's gonna kill me!"  He had left an ENORMOUS hickey right where my neck meets my right shoulder.  I told him not to worry about it, and I actually liked that he felt possessive enough to mark me that way.

We moved to the bedroom so that we could have more room, and that's when I decided to take off my boots, because I didn't want to wear shoes in his bed.  He took off his clothes and joined me on the bed, and I started sucking his cock, determined that he was going to cum more than once that night.  At this point I should mention that I had gotten waxed for the first time the day before, and then waxer was rather careless about it, and ended up ripping skin off of my labia minora very near to my clit on the right side.  This put a bit of a damper on our activities, because it was still rather painful to the touch at that point.  Tyler did attempt to finger me gently enough to make me cum, but I just wasn't able to because I couldn't relax enough due to my injury.  So anyway, I sucked Tyler's cock until he blew a large load down my throat which I managed to swallow.  

We snuggled for a while and talked until Tyler rolled over and took my panties off.  After donning a condom he spread my legs and proceeded to pound me hard in missionary.  I lifted my legs up higher so that he could go deeper, and his biceps bulging, he used his arm to hold my leg in place.  I found this to be an incredibly hot move and demonstration of strength, and he was hitting my g-spot with every thrust so it felt great, but I just couldn't cum in that position.  We decided to try me riding cowgirl, and after a long time of this, Tyler came again, but stayed hard so that I could keep riding him.  When I got tired, I decided I just wasn't going to be able to cum, so after a bit more snuggling, I got dressed and Tyler walked me back to my car.

When I got home Steve was waiting for me.  We climbed into bed, and after fucking in cowgirl for a while, I asked him to do me from behind until he came.  Finally, Steve made me cum by gently using my toy after which, we snuggled up and went to sleep.

Quick Update

Hi everybody.  Yes we are still alive and still in the swing set.  As a matter of fact, we've been quite busy little bees lately, hence the significant lack of posts recently.  As a quick recap: I met Tyler at his place for the first time, Steve met his new lady friend at a motel, Tyler came over for a 3-way, I met a new guy online and he came over for some fun in our driveway (OMG SO HOT!!), that same new guy came over for a 3-way and last but not least, Tyler is scheduled to come over tonight.  Whew!  Lots to tell you all, so please stay tuned! 

Stocking Filler

Merry Christmas one and all!  This is our official Stocking Filler post for HeelsNStocking.  So here goes...

In the Swing Set's most "wank worthy" posts... well this one is pretty easy for us as we just started recently so there are not that many from which to pick but the top ones would be:

• Mr. Uncut
• Our Very First Threesome
• The Head in the Parking Lot
• Our First MFM

And now for the Q&A:

1. What was your most memorable sexual moment? That is a tough one given how many firsts we experienced this year but I would have to say that the biggest one was actually the moment that I emailed Monica to tell her that Darla was coming home with me and that we were all having sex that night. That is a hard moment to forget. 
2. What firsts did you try this year? Wow, this is the big one for us. 2011 was the year of sexual experimentation. We had our first threesome (FMF) as a married couple and my (Steve's) first ever. We had our first threesome MFM. We each had sex with someone other than our spouse for the first time since we were married. And we each had "parking lot nookie" with people we had never met before. Monica made it to her first strip club. I'd say that those are pretty big firsts. I think that there will be quite a few more for next year too. Oh, and of course, we started a sexblog this year too! 
3. What would you like to try for 2012? More of all of the above ;) But of absolutely new things, we definitely hope to try out some swingers clubs this year and get into some foursomes with other couples. We have been sharing each other this year but have not actually tried swapping with another couple yet. Monica is very excited to try some bondage and spanking apparatus. We are still experimenting with the idea of having "regulars" in addition to having "ships in the night" threesomes. 
4. What’s on your sex toy shopping list for 2012? or what were your top sex toys you played with or reviewed of 2011? We don't do toy reviews but we do use our own regularly. This year the big toy for us was a double penetration "triple" vibrator that Monica really likes. She really likes the size and the variety of stimulation. We also played with a double dildo (with Darla) for the first time this year. That was fun. 

And now for some pics. Sorry, only Monica had pics ready to be posted.

A Surprise Meeting and a New Friend

Sunday evening I hopped onto one of the online communities that I frequent in search of new people to join us.  I often hop on and have low expectations - few people are real on those sites and those that are, women especially, are overwhelmed by people (read: men) trying to get them to go do something whether it be to send pictures, jump on the webcam, talk dirty to them or to head out to meet them right that moment.  So actually connecting with a real person that is willing to talk can be rather challenging.  I'm doing some searching online while Monica is out of town for a few weeks - hoping to find someone to line up for some fun when she gets back.  The secret is perseverance, of course.  You can't find someone overnight.  You have to put in the time if you want to actually find someone interesting.


I was happy to actually make a connection this evening.  A real, live woman to talk to.  Amazing.  We chatted for a little bit and it was clear that we clicked and that she was actually interested in something real, not just talking about it online.  There are ten people looking to learn more about their options for every one person actually looking to make something happen.  We talked about how Monica would not be available for several weeks and my new acquaintance was very disappointed to have to wait so long.  She asked if we could meet sooner to get the ball rolling, so to speak, and, of course, that was just what I was thinking.


She asked when I might be available.  I said most anytime this week, actually, even tonight.  She said, "Can you meet me in half an hour?"  Well now that was unexpected.  But I had nothing going on to keep me at home so I showered, changed back to real clothes (I was nearly ready for bed as it was) and ran out the door to run to the bar to meet her.  It was nearly a half hour drive between us so no time to lose.  It was after midnight when we decided to try to meet up.  This never happens, trust me.  Going from "Hi, how are you this evening?" to "Want to come out to the bar and meet right now to see if we'd be interested in a threesome?" all in a span of fifteen minutes simply does not happen.  Ever.


We met at the bar and had a beer together.  She is in her early forties so several years older than me and basically a full ten years older than Monica.  She would be, by rather a wide margin, the oldest woman I have ever been with both in absolute age and in relationship to my own age.  I've never been with a woman older than myself at all.  And I have never been with a black woman before.  So this could be a whole slew of new experiences for me ;)  She is tall and busty.  Just barely taller than me, and all legs, and nearly as chesty as Monica.


We met at the bar and each had a beer.  We talked for an hour before it was closing time.  We seem to hit it off reasonably well.  I walked her to her car and she asked if it seemed like this was something I was interested in pursuing.  I said, "Absolutely" and asked if she wanted to continue talking in the car.  Wink, wink, nudge, nudge.  I think we all know what "continue talking in the car" is code for around here.


We got in the car and the chatting was limited to just about one minute or less before we were making out and her clothes were starting to come off.  Her tongue was in my mouth in a flash and the buttons on her white blouse came undone very quickly.  She had on a tight black camisole that was pulled down to expose her thirty eight triple Ds almost instantly.  Who would have guessed when I hoped online at half till midnight in my pajamas that a few hours later I would be in the parking lot of a bar across town getting some?


We were stuck using the front seat of her rather small car.  Far from an ideal location for our activity.  When Monica has done this she had the convenience of an SUV with three rows of seats and blacked out windows, not to mention having planned out the location where the vehicle would be parked ahead of time.  We were stuck in front seat, no tint on the windows in a well lit parking lot right on a busy street.


Given our less than ideal scenario we kept our playing to only thirty or forty minutes.  We had a quite enjoyable time, to be certain.  She, like Monica, completely loves having her tits sucked on long and hard and Monica has trained me on how to do so quite effectively which, I think, left a lasting impression in this case.  She was concerned about how exposed we were and so did not want to remove her jeans so I was limited to pleasuring her with my fingers squeezed into her already tight jeans.  I did okay and she was insanely wet in no time.  So wet that she actually soaked completely through her panties, through her jeans and was getting the car seats very wet!


The bulk of our time was spent with me pleasuring her but I did get an opportunity, since I am generally unconcerned with getting caught in a compromising position, to pull down my own jeans and take out my cock on which she was eager to demonstrate her blow job skills - which were rather impressive.  Not as impressive as Monica's - Monica really does know how to suck cock better than anyone ever.  But tonight's sampling was better than most.  She took me deep and gagged on my dick several times while I just reclined and stretched out and enjoyed the feel of her throat.


It was not too long before she decided that she was so horny that if we kept on any more than she would absolutely need to have sex right then and there - which she has to wait for Monica to be available for.  So we called it a night but are hoping to be able to get together soon.  She is very excited to have Monica join us - she has never had a threesome before and is excited, and nervous, about having another woman.


So tonight was a complete surprise and an overwhelming success.  I have a feeling that meeting women interested in joining us may prove to be easier than we had anticipated.  I hope that this is not a fluke.  - Steve

A Few of Our Favorite Titles

So we like porn.  No big surprise there.  Monica was a porn watcher before we met and I have long been a big fan.  I got into it during my college years.  So we own a rather nice porn collection which is always growing.   It is hard finding porn that you really like.  Porn that you actually want to watch, like paying attention.


We use porn as "background noise" during sex most of the time.  Often we don't watch it at all, it just provides a soft flickering light and a little bit of sound.  But sometimes we want to sit down and really enjoy some excellent erotica - when we are looking for more than just hot, naked bodies but for erotic situations and stories.


We have found a few titles that really stand out:

• Pirates: everyone knows this one, the first real HD porn.  Huge budget.  A classic that you cannot pass up.  The sequel isn't bad but is nothing like the original.
• 1001 Erotic Nights - The Story of Scheherezade: This is a classic, sensuous movie from probably the early 1980s.  
• Looking In: Good story tackling voyeurism and spouse swapping.
• MILF Chronicles: Some great scenes and the storyline isn't too bad.

The Weekend Recap: Part 1

As you may recall, I had big plans for this weekend.  I was hoping to begin the festivities Friday at lunchtime, but alas, Steve did not come home for lunch, so that was a bust.  In fact, he got home from work rather late Friday night, by which time I was ready to run away to Bermuda due to the antics and general loudness of the 3 year old.  After putting the 3YO to bed, I decided that if we were going to get busy, I needed to unwind.  I put on my red plunge bra, black lace panties and my tall,  black suede, over the knee boots and after throwing a white button down shirt over the top, logged into my new favorite adult meeting site and turned on my webcam.    I immediately received a bunch of private messages, many of them asking me to start taking more off, but a couple of them were more conversational, so I stuck with those.  This being my first public camming session, I was feeling a bit shy, and wanted to warm up a bit before going topless.  When I did finally take my shirt and then bra off, I got so many private messages that I just couldn't keep up with them all.  Apparently a lot of guys like huge breasts, who knew?  Time passes quickly when a bunch of strange men and women are telling you how hot you are, and what dirty things they want to do to you.  Suddenly it was 2 am, I was extremely horny, and I could have cared less if I got any sleep at all that night.  After saying good night to my new "friends" I  went to the bedroom, collected a few toys and implements that I decided might come in handy, took off what little I had on (just panties and boots) climbed onto the bed and waited for Steve to get out of the shower.

When he came up to the bed and saw the things that I had spread out, he said "Oh, I see.  Get on your hands and knees."  I assumed the position and it wasn't long before I felt the welcome sting of the pleather paddle on my ass cheeks.  I jumped and sighed with every smack, and I could feel myself getting wetter by the minute.  There was a slight pause, and then I felt the sting of our rubber whip.  I really flinched when that hit, because it has much more sting than the paddle, which really barely qualifies as a paddle.  I took several more lashes of the whip until a really hard one landed causing me to whimper "Ouch!"  Steve felt really badly that he had actually hurt me, and that was the end of the whipping for the night.  We are new to spanking and are both trying to figure out how hard I want to be spanked, so as we test my limits, these things are bound to happen occasionally.  I wasn't upset about being whipped too hard, I just now know what my upper limit is for the moment, and I know that I don't want to come that close to it while we're playing.  I'm hoping that Steve will still want to whip me upon occasion, because up until that point, the sting of the whip was making me very wet. 

We switched back to the paddle, and after paddling me on my ass, thighs and pussy, and a few bare-handed spanks, Steve decided he wanted to finger me, so I flipped over, and between the hours of camming and the spanking, I was very wet and very ready and I came hard after just a few minutes of having my clit rubbed while my nipples were sucked.  I told Steve that I wanted to try for a second orgasm, so he suggested that I suck his cock for a while so that I would have time to recover.  I don't need to be asked twice to suck cock, so I eagerly moved down between his legs and licked and sucked and gagged on my very favorite cock until Steve told me to grab a condom because he was ready to fuck me.  

Since we knew that a second orgasm would take a long time to achieve, we decided to try a desensitizing condom.  We had never used one of these before, so didn't know what to expect.  I slipped the condom on then mounted cowgirl-style and attempted to ride my way to an orgasm.  At this point it was after 3am and Steve was exhausted since he had been up for 22 hours at that point.  I told him that he could relax and I would do all the work.  After at least 20 minutes, I decided to grab my rabbit vibrator and pressed it against my clit, while continuing to ride cowgirl, until eventually I came again.  Success!  I flipped over so that Steve could finish doggie-style, but it ended up that the desensitizing condom worked a bit too well, and we decided to finish with me kneeling on the floor while Steve jerked off until he came all over my tits.  After we cleaned up, we collapsed into bed and quickly fell asleep.