Quit laughing, I am serious. I am not talking about sliding a few fingers in here and there to gauge her wetness or you adding in a little finger play while going down on her. I am talking about fingering and nothing more.
Stumped? My guess is (depending on your age) it has been some time and probably goes back to your teenage sexual exploration years during some hot and heavy make-out session. It seems that fingering drops off the menu once you “advance” to other acts and it is a damn shame. Maybe the issue is the name of the act. Unlike oral sex which has a degree of foreign allure with terms like cunnilingus or fellatio, which elevates blowjobs and eating her out it to a sexy degree of sophistication, fingering has no other terms and just sounds juvenile or worse invasive like a pap smear. It holds no taboo and it is one of the few sex acts she can do all by herself, so men tend to forget all about it.
Well time to quite overlooking this underappreciated act. Fingering her can feel quite refreshing and often unexpected. Most women haven’t been THOROUGHLY fingered in a very long time. Fingers can give much more focused, deliberate, and intense stimulation than any other body part. You can also use one hand inside of her and the other on her clitoris. The combination of internal and external sensations does wonders.
Sounds easy, huh? Well, now I am going to tell you how to make this even better.
This isn’t just a foreplay move with the hopes of advancing to other stuff. I’m talking about fingering as an act all in itself. Don’t worry, you’ll get rewarded later. Trust me.
Let’s start with some basics. Make sure your nails are trimmed and filed. Avoid spicy foods on your fingers and obviously, wash with soap and water. Do not use hand sanitizer!!
Ok, now this will all seem basic but it is key so spend time kissing her, slowly removing her clothes, and running your hands all over her body. Don’t rush it, build up that anticipation. Get yourself comfortable so you can use both hands. I like to get myself sitting up next to her as she is lying down on the bed. I love to trace my hands around her lips and pump my fingers in and out, slow and gentle, and build up the intensity while using my other hand to brush and tease her clit.
Unlike oral sex, fingering allows you to look into her eyes as you are in charge of her pleasure. You can watch her respond to your every touch and when she makes eye contact as she feels that you love giving her pleasure and making it all about her…that look never gets old and an amazing turn on.
Craig and I couldn’t help but notice her. She stood out, unlike the line of boring soccer moms standing in line for coffee that Monday morning, this woman looked fun. We commented to each other that she looked sexy and frankly couldn’t help but notice those large full breast hidden under her blouse.
We watch as she ordered her coffee and to our surprise, she sat next to the table beside us. Craig and I talked among ourselves and I noticed she was looking at her phone pics. I caught a glimpse of a picture of her with her breast peeking out of her blouse. She looked up at me and I was caught. I smiled and could tell she was embarrassed. I joked, “That is nothing to ashamed of”. She nervously laughed and sipped her hot coffee. Since I had broken the ice, we pulled her into our conversation and eventually laughed at me catching her looking at her naked selfie. Craig laughed, “Hey Tom, I haven’t seen the picture you are talking about. Not fair’. She giggled and said. “Perhaps I’ll send you both that picture and more when I am out of here to avoid further embarrassment”. We talked a bit more and then we all left. Craig and I pondered if she was toying with us and thought nothing of it.
Later that evening, my phone goes Bing and there was that picture followed by some more. Each displaying an adorable brunette with luscious full 42DD breasts. Wow, I thought. Craig sent me a text, “Holy shit, you were not kidding, those are amazing.”
I sent her thanks and said we should hang out sometime. She responded back, mentioning her busy schedule and that the only time she had free coming up was Wednesday. That was the day that Craig and I were supposed to go skiing, but her slopes looked far more inviting that the ones we were planning to hit and I thought of how I might weasel out of hanging out with Craig.
Craig was an old college friend and was back in town for a week and one of the few guys whom I can even tolerate hanging out with for any length of time. It would be really shitty of me to blow him off, but damn, I was tempted.
I told her of Craig and my plans and suggested we get together another time and then she mentioned that she would love to come along. I said I’d run it by Craig and he was more than happy to have a ski bunny joining us.
We like to hit the slopes early and end by noon, so told her we would pick her up at the coffee place and then head up to the resort. We arrived and she looked super cute. We quickly realized that we didn’t know her name. “My name is Sherri”, she said. We made no mention of the naked pictures of her, but both Craig and I couldn’t erase the images of her as we drove to the ski resort.
We arrived and Craig and I got our skis from the rental place and asked Sherri what her skiing level was. She laughed. I don’t ski? Oh? I was puzzled, did she want lessons? She then told us she was a freelance travel writer and this was a new resort so she was going to see if she could get a tour and check out the new luxury suites they built for guests.
We skied thru the morning and arrived back at the base. I picked up my phone and had a text from Sherri:
“Guys, you have to see the suites here at the resort. I was able to get us a room. Meet me in room 404 and relax. I’ll have drinks ready”
Wow, this beats hanging out at the bar and so we made our way to the room.
When there, we were greeted by Sherri. The room was large, with the big window overlooking the mountain. Sherri had snacks laid out and poured us a drink. Not bad way to end a morning of skiing. We snacked, drank and laughed and the conversation started to get frisky with jokes about making full use of the room. Sherri then stood up and kissed me and pulled Craig behind her and he kissed her neck, then her lips. His hands on her hips, kissing the back of her neck, I was in front, hands on her ass. She was now feeling the heat of us both.
He unbuttoned her blouse as I kissed her passionately. We stepped back to look at her standing there. She was flush, her blouse unbuttoned revealing her bra covered breasts. She moved towards us and removed our shirts and pulled us towards her. My bare chest was on hers as he slipped off her blouse and unhooked her bra revealing those delicious breasts. I moved down to suck on her nipples and caressing a breast in my hand as he moved to do the same with the other. She looked down at us both working her tits and the gentle moans fell from her mouth getting Craig and I more and more turned on.
Craig moved up to kiss her lips and I took both breasts into my hands and rubbed and pulled slowly on her hard nipples. He then moved up behind her and she felt his hardness in his jeans against her pants and held her breast in his hands feeding them to me.
Eventually, we lifted her up into our arms and carried her to the bed. We laid her down on the bed and pulled off her jeans leaving her in just her panties. She sat up as we stood before her at the edge of the bed, she noticed us straining in our jeans and finally reached over and pulled off our pants and underwear revealing two huge erections.
We stood before her, stroking our cocks, telling her how sexy she was and how much she was turning us on. Her hands soon replaced ours. She stroked us each and moved her mouth from one to the other. Our hands softly pulling her hair and playing with her breasts. She licked up and down my shaft then back to him and then looked at us with lust in her eyes and rubs our wet cocks over her nipples.
We reached down and pulled off her panties and Craig moved between her legs and started to lick and suck as she worked my hard cock with her hand and mouth. She laid back on the bed, pulling me with her. Craig continued to eat her out as she sucked my cock. I started to kiss down her body as she took me deep into her mouth and I pulled her legs apart for him as he continued to lick and we took turns tasting her sweetness. We then both started to finger her together as she gasped, followed by a small tremble as she squirts.
I slipped my wet fingers out and cradled her head in my lap feeding her my fingers as he slowly entered her with his cock. My hands softly caressing her face and breasts as he fucked her slow and deep at first. I watched him fuck her as she pulled him in deep with her thighs. Sherri’s hand then reached back for my cock and she stroked me in unison matching his cock’s rhythm. He then looks at me and I read that non-verbal signal. He pulls her into his arms, cock still deep inside and lifts her up. I assist and cradle her ass so she can comfortably ride him while he is standing up.
She riding him hard and it is making his knees weak, so he turns and falls on the bed with her on top of him. She keeps riding him hard and I sense he is having a hard time not cumming as she bounces on him with those big tits shaking in his face. I lift her ass slightly which causes Craig to slip out and I quickly replaced his cock with mine filling her deep as I take her doggy style.
I feel my cock plunge into her as she moves to take Craig into her mouth. I fuck her as she moves her mouth up and down his shaft. We continue to work her from both ends and our desire increases and we all begin to feel that combined heat. I slap her ass as I fuck her harder, pulling back her hair as I leverage and watch his cock going into her mouth.
She screams out that we are getting a tad too rough, so we respond to her plea and slow down the pace and I begin to feel her twitch and grasp my cock with her tight pussy.
Not wanting to cum yet, I slip out and move down and start to eat her ass. She continues to suck him and her moans get louder as I tongue her butt. I then begin to finger fuck her pussy that is still pulsing from my cock.
Sherri is screaming with pleasure, so much so, that she can’t suck Craig’s cock, so he gives her a rest and positions himself under her and licks that swollen clit as I work that ass. He is sucking her clit and those lips as our fingers explore her. I pull her ass cheeks apart to fully tease that ass with my tongue. We slowly work our way back up to her face. Massaging her ass and back as we move up her body. We take turns kissing her, she tasting her creaminess off our lips. We roll her over. All of us glistening and aroused as our hands work her breasts as we kiss her. Our hard cocks throbbing at her side.
We ponder a bit of what to do and Craig and I smile at each other. Craig looks at me and I laugh. I pull her legs apart and start sucking her toes as Craig moves and slides his cock back into her wet pussy. I hear her moan and his moans as well. I watch a bit, stroking my hardness rubbing my cock over her nibbles and lips. He is fucking her hard and deep. She pulls her tits together and he tells me to titty fuck her as he fucks that wet pussy that is soaking his cock.
Ever since I saw that pic at the coffee shop on Monday, I had visions of my cock between those beauties and it looked and felt more fabulous than I imagined as my cock was sandwiched between her breasts and as I glided between them she would lick the head of my cock and grab my ass. All the while I could hear Craig fucking her and I could feel the warmness in her chest as he was getting her close to orgasm.
She clinched and pulled Craig in and no longer were we in control. She was fucking him, rocking her hips while squeezing her tits together as I fucked them while she teased my cock with her tongue and licking her nipples. This was now sending me over the edge. We could no longer hold back and I heard the deep moan from Craig as he came, her pussy milking every drop. Her face flush and in the throes of orgasm was just the sight that had me releasing my load all over her breasts.
We laid there, our bodies tangled as we came down from the incredible sex high, tenderly touching and kissing. Craig then got up and started to run the shower to clean up. Sherri and I made out like high school kids as we lie there, her body still warm and sticky with my cum.
I took Sherri’s hand and we joined Craig in the shower to cleanse the sex sweat and cum off of us. As we soaped each other up, I decided I need that pussy one more time, so I glided my cock into Sherri and Craig worked her soapy tits. The water continued to cascade down upon us and Craig dropped his knees and I positioned myself so that he could lick her clit as I fucked her.
My cock was deep inside her once again and my hands grabbing on her tits, his tongue darting over her clit as the warm water and steam surrounded us. It didn’t take long before she was once again cumming.
She quickly dropped to her knees and took both our cocks telling us she wanted to reward ourselves one last time. We smiled and she licked and sucked us each pulling us closer and looking up at us with devilish intent. She felt us getting close and worked us just right to the point where we both came all over her at the same time.
We get out of the shower, spent and get our clothes back on. She had to be back home that evening so we checked out of the room and hit the road back filled with smiles asking ourselves when we are doing this again.
I’ve always been aware that I have had (and continue to have) a more adventurous sex life than many of my peers. I’ve known this for quite some time and have only occasionally questioned it. I have been told that I’ve been blessed with good looks, but I am humble and anyway that alone doesn’t cut it. Small doses of minor fame have occurred, but in this day and age, hasn’t that happened to everyone? Most people would agree that I am basically a quiet and private person, yet I readily seek and indulge attention. Just looking at my careers and circle of friends reveals this to be the case. I have always been comfortable with myself and never sought to be part of the popular crowd. One could conclude that it was the years of leading a nomadic life, moving around the world, that led me to become comfortable and self-confident with my individuality and somewhere along the way my shyness morphed into some kind of mysterious appeal.
My sexual exploits have always been fairly private and only alluded to in certain forums. Fear of character misinterpretation, judgments, shock or even worse, construed as gloating have prevented me from opening up and exposing this part of me until now. I’ve decided to share my revealing and sorted, yet exciting and apparently adventurous, torrid tales here. The stories I will share are true and any opinions I might express are solely mine. Only names and places have been changed simply because nobody is innocent.
Early on, even before I knew what it meant, I was very interested in sex. My parents were not some wild and crazy sex fiends, but they weren’t prudes either. Dad subscribed to Playboy and they weren’t hidden under the bed or in a closet. It was there for the reading and I would page through them at a young age, not knowing anything more than these were just pretty naked women. I recall fantasizing about licking the whipped cream off the model on the famous album cover by Herb Alpert & the Tijuana Brass. I had no clue this was a sexual thought. When the girl who looked after me when my parents away wore a pair of jeans with a patch on it that said “kiss my ass”, I remember thinking to myself that might be a fun thing to do. I didn’t know she was wearing it as an insult.
Eventually, I became aware of what sex was and I quickly began filling my head with everything I could about this topic. My parents had divorced so no longer was Playboy an easily available research tool. My major source material was now Mom’s subscription to Cosmo. Weird as it may sound, I learned a lot from that magazine. What woman wanted sexually from men, what annoyed them about my gender and lots of tips on how a woman could get more out of sex. One article I committed to memory was on female masturbation tips. This was like the holy grail of my early studies. This article was the education I needed. Now I was confident I could jump start that engine once I got under the hood. I was quite fascinated by this. I shoplifted a copy of The Joy of Sex and read it as well as digesting every bit of information I could from a paperback copy of The Hite Report. This information was never shared with others nor was it discussed among my friends. I was keeping this to myself and I was slowly starting to put my education to work.
When my family moved yet again, I was almost 15 and I had already applied some of my schoolings at my last two residences but nothing like would happen when I met Lisa D.
The D. girls lived down the street in the huge house with the pool. Liz was a senior in high school and her younger sister Lisa was my age. I didn’t get to know Lisa until about a month after we moved in and that was the first day of 9th grade. I was once again the new kid and Lisa introduced herself to me. We would talk at the bus stop, but I was the kid with the I don’t give a shit attitude who early on made a few flippant remarks to John Jerkanellis scoffs and insults that were hurled my way and had safely cemented my status as the “outsider. Lisa, it turned out was part of the elite popular gang and dated John Jerkanelli, so acknowledging me in her social circle was taboo.
I didn’t hold this against Lisa as she was nothing but nice to me at the bus stop and occasionally would invite me over to her house to study and listen to music. Unlike the rest of the rah- rah gang, Lisa shared some of my music taste and we would often listen to records together. It was during one of these listening sessions that the topic of sex came up and I suddenly discovered that I was far more sexually experienced than Lisa and was even more shocked at how unaware she was of some things. I began explaining things to her and it clearly caught her interest. I revealed what I had studied and I was pretty receptive that perhaps more than just having me explain this was on her mind. She scooted over to kiss me one day and soon this progressed into me being “her little secret”
When summer began, our secret sessions consisted of me applying everything I read about manual and oral female stimulation to my willing friend. Suffice to say, I spent much of June with my face between her legs. I would make mental notes of her bodily spasms and clenches. I would pay attention to not just her clit but also the other parts of her genitalia that she liked to have touched. I would have her show me and tell me what she liked. I’d mix up the paces with light and strong touches, knowing that contrast was paramount. I quickly learned that to really give head meant learning how to incorporate her *whole* body into the act. I would caress her breasts, the inside of her thigh, and the small of her back. My goal was sensory overload and not just beating the crap out of that one-inch area of genital flesh. I loved it and couldn’t get enough of it…even if it was a one-way street. Lisa had made things quite clear that she was only going to do those thingswith Jerkanelli and then when the moment was this fairy tale perfect setting. I was baffled a bit, but I accepted that and didn’t complain, as I was quite enjoying my tasty pudding treat.
One steamy July afternoon, I made my way up to the house only to be informed by her sister Liz that Lisa had gone with John Jerkanelli down to the shore with his family. Thoughts of exploring Lisa’s naked body were silenced and I had planned on turning around and heading back home when Liz offered the invite to use the pool.
It was a stinky hot day and the idea of a dip was inviting so I ran back home, changed into my swim trunks and promptly returned. There was Liz with her friend Lori sitting around smoking pot and as usual, the parents were never home (I never saw them and I question to this day, whether they existed). It didn’t take long for the girls to begin the inquisition.
Liz knew for a fact that something more than listening to Cheap Trick records was going on between me and her sister and she seemed to relish in the fact that her sister was being bad. I still didn’t tell Liz anything, but apparently, she knew something was going on with me and her sister. She must have told her friend Lori because when Liz went inside to take a phone call, Lori told me what they had assumed I had been doing. I confess to Lori that things had not progressed to the degree they assumed and it was pretty much me making out and orally pleasuring Lisa and nothing more. Lori gave me a look and made it quite clear that she could make me a very happy young lad if I was game. Hmm, I wasn’t Lisa’s boyfriend, so why not and let it be known that anytime she wanted to start down that road, I was ready.
The conversation continued and then Lori made the move. I was now kissing her and exploring her body in the pool and vice versa and then Liz returned.
What are the two of you doing? Liz yelled and then jumped into the pool with us. There I was naked with Lori in an obvious state of arousal and now had Liz with me as well and she starts kissing and fondling me as well.
This was way too much for my 15-year-old brain to handle. What is going here? Is this a cruel prank? Are you girls sure you should be doing this? Liz and Lori just laugh and rubs their breasts in my face as the both stroke my cock.
I was stunned and in shock. Lori grabbed my hand and assured me everything is fine. She proceeded to take me into the house and up to one of the rooms in the home. Liz and she resumed what we started in the pool and there I was, naked with two women. Each taking turns Lori fucking me. It was turning into one glutton filled feast of pleasure.
I knew this was a one-time thing and I wasn’t going to ruin it by begging for more. I thought I peaked and how can I ever top this? I’ve peaked at 15!! Little did I know that there was a lot more in store in my future.
I would occasionally get together with Lori, but Liz, being Lisa’s sister, wasn’t going to hook up with me again and I knew it. I would still get together with Lisa, but they soon grew less and less frequent as I was expanding my circle of friends and she was feeling guilty about having me as ‘her little secret.” I don’t think she ever found out about that afternoon. Years after I had graduated from college, I ran into Liz again, but that is a whole other chapter.
I’ve been the other man, the guy on the side, your girlfriend”s little secret and your wife’s favorite sex toy on more occasions than I care to mention. With the exception of one instance, I would not classify any of these intimate friendships as a full blown affair, nor did they constitute a “one night stand.” While sex was the obvious core of these trysts, there was a definite friendship and dare I say feelings of care and compassion.
I didn’t wake up one day and say to myself, “I think from now on, I am only going to fuck attached woman.” These instances just happened. Believe what you want…I was never the initiator of these flings, so don’t think I sat around at night plotting whose wife or girlfriend I was going to seduce. I could have been the “better” person and politely declined, but I rarely did. I was cool with the situation. I wasn’t looking to replace the main squeeze and I always made sure to know exactly why she wanted to pursue this possibility. If she was looking for a no strings romp with a friend who knew how to keep his trap shut, then I was the ideal playmate for the woman seeking a little something extra.
These rendezvous relationships would start out strong. Initially lustful intent would blur the vision of reality and the sessions would be frequent. Eventually, I would find myself scheduled into their social calendar where I would spend afternoons and weekends frolicking under the guise of “studying” or “meeting for lunch”. Lunch took on a whole new meaning. My place, her place, hotels, her girlfriend’s place, offices, and various locations were converted to dens of sin. Once I was even flown to a hideaway in Napa for a week of “service” (that is a whole story in itself). Occasionally feelings of guilt (or worse discovery) would bring the flings to a halt or my “novelty” would wear off. There were the few times that the boundaries of emotion were crossed. In most cases, a serious evaluation would occur with the relationship questioned and placed back on course.
I don’t know if being the “other man” is different than being the “other woman.” I wasn’t spoiled with jewels or fabulous vacations (that trip to Napa doesn’t really count). I had no grand illusions that she was going to be “mine.” It was simple. She would call and say “I have this time free and I want you in my bed.” I saw no reason to say no.