When is the last time you thought about getting fingered? What? You haven’t thought about it in 20+ years? Me neither! It’s a sexual act that falls to the way side once the nuptials have been completed. Or in my case it was. Foreplay became nearly obsolete. The only thing entering my vagina after marriage was my husband’s hard cock. Occasionally, a finger in the ass. I can’t recall my husband fingering me (even in the early days!) I had no idea what I’ve been missing!
“Bad sex” has been in the headlines lately. You can count me as one who has definitely experienced my share of “bad sex.” And some of those memories are from bad fingering. Ramming. Jamming. Dry. Unpleasant. Horny teenagers and young adults who didn’t know how to talk about sex or pleasure or consent. Boys who didn’t know how to use their hands with finesse. I could see on the face of my lovers that they thought they were doing “it” right. I have this horribly vivid image of a guy in my head with his gritted teeth, sweat beads forming as he fingered the FUCK out me saying over and over in a thick Kentucky accent “you like that? you like that?” Fuck no, I didn’t like that! I couldn’t walk properly for days!!
Getting fingered wasn’t all bad. Sometimes it was good. But, like so many young women, I was naive and unsure of myself. I never spoke up or joined in by touching my clit while I was being fingered. I feared not knowing what was “normal.” I feared being called “weird” or “kinky.” I, for damn sure, NEVER had an orgasm from being fingered. And after 15 years of marriage those memories were very dusty and faded. Fingering isn’t something that had even occurred to me for years! It never crossed my mind that fingering can be as pleasurable and orgasmic as penetration from a cock! My husband and I had a pretty standard routine. We’d spiced it up a bit over the last year by adding in some anal sex, the purchase of a new vibrator (yep, my fabulous Shibari) and having sex more frequently. But basically it went like this: blow job, penetration, use my vibrator to cum, he cums on my stomach, good night. Yawn.
In November I separated from my husband. This was my ticket for more exploration, more escapades, more sex! The sex I had been so hungry for over the last year and a half. *A note to the hungry: It is unbelievably easy to have sex if you just want to have sex. * It’s as if I’ve been wearing a sign on my head (or ass) that says “Fuck me.” My pheromones must be enveloping me like a cloud. An invitation for the starving to be fed. And although I’m on Tinder and had a few Tinder dates, dating sites are not where I’ve found the majority of my lovers. Four of my recent lovers have come from being in the right place at the right time: proximity! And this is how I met Alex.
Alex is about 6’3″ with a slender build and great shoulders. He has light brown (probably blonde as a kid) straight hair that he keeps cut short. He has a very defined widow’s peak and his hair is always combed back or up. He has a dark beard that comes and goes, I’ve learned. Without the beard, his smooth skin makes him look 16. He has strong eyebrows and almost glowing light blue big eyes, surrounded by thick long lashes. He has a huge, full-toothed smile. His mouth is always slightly open when he’s smiling like he’s about to say something really flattering. And little creases form at the corner of his eyes when he smiles. Never patronizing, always genuine. The first time I saw him was the second week of December. It was a Sunday night. I was hung over and tired from being out late the night before at a holiday party. I was regretting having organized a get together for my preschool mom friends at a neighborhood bar. But, in truth and form, I do love being a good hostess so I showed up to the bar 15 minutes early to make sure everyone felt welcome when they arrived. When I walked in the door of the bar my eyes scanned the room. Alex, who was bartending that night, gave me a big welcoming smile and head nod. I didn’t know him. I’d never seen him before. But the air was immediately electric. By chance some friends of mine were at a table having drinks before dinner on their “date night.” I sat down with them. The table was centered on the wall about 20 feet from the bar. I chatted with them for a few minutes and when I looked up, there was Alex giving me that big smile again. I looked around to see if he might be looking at someone else, but we were the only people around.
What I came to love about Alex that night is that he makes every single person who comes up to the bar feel like a superstar. When he looks at you and takes your order, you feel special. Since that first night I have watched woman after woman after woman dazzled by him. I can see their imaginations, dreams and lust when he turns to pull the tap or grab a bottle from the glass shelf. It’s not a show. It’s genuine. He enjoys making people feel good. When my group of mom friends showed up we spent much of the night whispering about how “hot” the bartender was and how he seemed to fancy several of us. He was engaging.
For the rest of the night Alex and I caught glances of each other, but he never tried to strike up a conversation other than to take my order. Maybe he was nervous? I know I was nervous. He ended up getting off work while our party was still there. My friend and I had our coats on and were about to leave when I noticed he was looking at me again. We took our coats off, ordered waters, sat back down on the barstools and said goodbye to all the other moms. Alex walked toward the back of the bar with a full beer. I was certain this was a silent cue to follow him. We stood side by side in the karaoke room, an open invitation to start a conversation. Clearly we were both very curious about one another. Finally we started talking. I had promised myself I wasn’t going to stay out late. (I wasn’t even wearing cute underwear!!) Instincts told me that sleep depravation would be well worth it. We ended up talking for the next two hours intermingled with my friend and I singing some karaoke. Alex asked, “So are you with the preschool mom group?” I put my face in my hands, embarrassed that I’d been outed. He said, “No! They’re great! Really nice, funny ladies!” He wanted to know how old I am. I replied: “I’m old enough to have gone to college. I’m old enough to have traveled to 40 countries. I’m old enough to have given birth to 3 kids.” He persisted. I rolled my eyes and kind of whined, “I don’t want to ruin my chances of making out with you!” He said, “Oh, don’t worry! There’s no chance of ruining THAT.” After I sang Sexual Healing he said, “Wow, that was palpable. The sexual tension and energy in here is crazy.”
A little after 1am I found him in the main bar chatting with a friend. I was so exhausted from the night before and said I was going home. He rather enthusiastically asked if he could give me his number? My brow scrunched up. Really? What a lame way of saying “this was fun, but not interested.” I said “You could just walk me out to my car.” He said he didn’t think that was a good idea. He asked if he could have my number. I said, “you could just come home with me.” He kind of froze up and I realized that his friend (girl) was standing close by. Again he said, “I don’t think that’s a good idea.” With no expectations I gave him my number thinking he had no intention of using it. I felt depleted, rejected and bummed when I got in my car alone. The sexual tension had been so strong between us.
Minutes after I got home, my phone dinged. Alex asked when he could see me again. He apologized. He hadn’t wanted to leave with me because there were too many of his co-workers, customers and one of the bar owners around. Plausible. Ok, whatever, no explanations needed. I just want to kiss those lips right now!! I said now was a good time. 2am on a Sunday night. I felt just like Phoebe Waller Bridge in the opening scene of Flea Bag. Anxious, anticipatory, giddy, but wanting to totally play it cool. Uh, yeah, it’s 2am on a school night! Alex is 25. I’m 42. We were about to embark on a super hot night of sexual escapades. Yes!
I had just moved into my apartment a few weeks before. I had no furniture. Only a mattress on the floor and 2 lamps. I led him by the hand to my room. Both of us saying we’d never done this before. I asked how many women he’d gone home with after a shift. He said, “None. Really. You’re the first.” Whether truth or fiction, he’s damn good at making a girl feel special. I sat down cross-legged toward the top of the mattress. He was sort of sitting with one leg off on the floor. We talked for a few minutes. Then I said, “Do you want to kiss me?” He nodded a quiet “yes” and literally crawled toward me from the foot of the bed like a lion about to pounce. His beard seemed to be the softest hair I’ve ever felt. We kissed and kissed and kissed and kissed. His arms were so strong. He put his hand around my throat.* He kissed me hard and passionately. I loved running my hands down his square shoulders and through his soft hair. His body seemed so freshly formed. There’s quite a difference between the waist of a 25-year-old and a 49-year-old man. Everything was more smooth, more firm, more chiseled. I had no qualms about my body. I knew Alex wanted every inch of me. His hands felt so good on me. Perfectly formed hands. Not soft. Not too calloused. Long strong hands. He has tattoos, but not heavily tatted, at least not in comparison to many around here. He said he makes music and videos with his brother. And he’s sort of in a few bands, heavy metal bands. He’s just not one of those people you look at and think: heavy metal. Quite the opposite. My initial arm-chair psychological evaluation would be: perfectionist. His hair, his clothes, his hygiene/personal care.
Ahh, and this. This is where paying homage to fingering comes in. Holy shit. I guess being closer to your teen years than your mid-life gives you way more recent experience and time for perfecting fingering. When you’ve had to resist “doing it” on many dates, you finger instead. Fingering! Alex is a master (or, um, a perfectionist?)! I can see him sort of sitting between my legs looking at me as he placed his finger in my pussy. His mouth slightly open, tongue touching the bottom of his upper lip as he felt my wetness. He was really fucking good at licking and sucking it, too! He could actually penetrate me with his tongue in a way that I’ve never experienced before. He went down on me for awhile. And then fingered me with perfect rhythm and pressure and discovered something I didn’t even know I had: my G-spot. I was on the ceiling. I came from being fingered! I came so many times that night. I haven’t even mentioned his perfect cock. Large, but not too big and he used it very well. Smooth. Well-kept, like the rest of him. The best thing about having sex with the 31 and under crowd is their ability to go and go and go again. Because so can I. And the best part: we both did “new” things. That’s probably my favorite part about being a MILF. I’m not only willing, but LOVE, doing things their age-counterpart lovers/girlfriends won’t or don’t. For me, the “new thing” was a sexual position that I’ll call The Squat. I was on my hands and knees and he was able to squat over my behind and penetrate my pussy by doing fast squats. That takes a lot of leg and core power on his part! And the new thing he got to do is finger my ass! Dreams really do come true, Alex. It prepped us for our next adventure together that will have to be separate post.
I want to end with my new found appreciation for fingering. If you haven’t been fingered in years, do it tonight. It’s now something I crave. I’ve made it part of my routine with new lovers. It has become the main source of pleasure with a current lover which is a whole other topic and post. But I’ll say that with this current lover fingering has become not only a way that we connect physically, but also emotionally. I’m grateful for it. He can hold me and kiss me while he’s fingering me and it becomes this incredibly emotional moment when I cum that sometimes brings me to tears. I feel closer to him because of it. The intimacy of my lover cradling me with strong warm arms while pressing his face next to mine and feeling me cum is so deeply moving.
Dear fingering, I love you. And, dear Alex, thank you so much for showing me how incredibly awesome fingering can be! You do it so well. XO
*I seriously need a separate blog post for this part. That was my first time every experiencing being “choked.” It was new, unfamiliar and a little scary. But my feeling on that has completely changed over the past few months! It didn’t tarnish anything about that night. When we paused I just asked him not to do it again. And he 100% complied. And as is my way, the next time we were together I told him I’d changed my mind and now I DO like it. I’ve found that the 31 and under crowd is all about the choking. I had never ever done it or liked it or knew that it could be done in a safe, sexy way. Now I ask for it with boundaries in place.