DILF Loving and Sharing – Part 1

This true story describes helping a DILF named, “Tammy,” recover from a nasty divorce. As well as regain some well-deserved confidence and finally explore her wild side. Basically, setting the stage for Part 2. I’ll gladly post Part 2 assuming Part 1 proves worthy of your collective time and effort.

I met Tammy on a dating site for older singles. I’d honestly posted that I was a late-50s married while male (MWM) who was temporarily separated from his wife due to a six-month military assignment. Thus, seeking a casual relationship. Specifically, a dinner and dancing partner while exploring the St. Louis, MO, area during the next several months. As well as, hopefully, more than the vanilla sex that I was getting back home.

However, I’d had no problem scoring some ass during previous visits. Mostly MWM cubs with paternal issues. Seeking a daddy bear like me to fuck their legally tender young faces and bottoms. Frequently for the first time or first time in a long time. Thanks to my goldilocks, meaning neither too big, nor too small, sized cock. Teaching them how to give far better head than I received at home. Specifically, edging, “good-to the-last-drop,” swallowing head rather than my wife’s spitting quickies. Thus, I was primarily seeking an ongoing female FWB rather than a fantastic fuck.

Naturally, my first several responses were from curious females seeking something far more long-term. Thus, they had no interest in a MWM. However, Tammy was an early 50’s Registered Nurse who’d recently divorced some bastard. Thus, she was far more interested in venting her frustrations than quickly dismissing my post. Obviously eager to discuss what happened with her marriage with a MWM like me. Perhaps gaining some insights.

Specifically, Tammy’s ex frequently visited several notoriously wild strip clubs and adult arcades in East St. Louis, IL. Yet, steadfastly refused to bring Tammy along. Claiming he simply watched the strippers. Nothing more. Implying she was too old and unattractive to sufficiently retain his interest or even accompany him. Yet, he’d become insanely jealous if she even looked at another man. Tammy reluctantly put up with it, rather than leave him, for the sake of their kids.

In addition, he rarely fucked her. Typically, only after visiting one of the adult places and apparently discovered a new toy or technique to bring home and try on her. Lots of DP and DV with the toys. Undoubtedly replicating what he enjoyed doing, or hoped to do, with other couples at the clubs. As well as over the edge of the bed deep throat fucking, ass-to-mouth, and occasional bondage and spanking. She’d submit rather than risk waking the kids. Plus, the occasional kinky attention was better than nothing. Of course, her submission secretly made my cock throb, since my wife typically waived off such attention.

In response, I explained that her ex undoubtedly did more than watch the strippers. Particularly after Tammy sent me a few of the XXX pics that her ex had taken over the years. Showing he was about 8 inches and thick. Thus, undoubtedly cruising for couples seeking an aggressive “bull” or cubs seeking a daddy bear. Likely coming home and banging Tammy particularly long and hard when he failed to score anything better. Unfortunately, the bastard used the pics as leverage during the divorce. However, they clearly showed Tammy’s huge tits and gorgeous pussy and ass getting pounded by his big dick. Thus, they secretly made my cock throb.

Tammy finally left the asshole after he began seeing another bitch. With fewer wrinkles and a younger ass. As a result, Tammy was extremely depressed and seeking a fresh start with someone far less selfish and controlling. With her ex quickly moving in with the other bitch and Tammy moving back in with her elderly parents. Thereby facilitating the sale of their former house.

Since then, Tammy briefly dated a guy who was super nice. However, he proved to be far too boring. Particularly after they finally fucked. With her waving off a few other guys since then. Worried they’d either be similarly boring or seeking a quick “one and done” piece of ass.

Thus, while I couldn't offer Tammy a new long-term relationship, I suggested letting me help her, “live a little,” before jumping back into another serious relationship. Promising to be around for at least several months before returning home. Seeking far more than a quick piece of ass. While she served as my tour guide. Totally my treat since the divorce left her with little money as well as confidence.

As a result, Tammy eventually agreed to meet me for dinner at a nice restaurant. Just dinner, since she steadfastly promised, "No sex!" Since she neither had, nor ever would, first-date fuck someone. Of course, I replied, “No problem!”

During dinner, we got along great. Discussing family, careers, and the numerous sights I’d hoped to see in and around St. Louis. Particularly as the wine flowed and our pretty young waitress sensed a “hook-up” in progress. Eagerly chatting with us and asking all sorts of probing questions since it was a relatively slow weeknight. Frequently complementing how good we looked together and got along despite it being our first date. Basically, hinting, “You really need to fuck this guy!” and, “seal the deal,” whenever she locked eyes with Tammy despite the wedding ring on my finger. Earning herself a particularly generous tip. Tammy’s gorgeous college age daughter had similarly replied, “Why not?” when Tammy mentioned meeting a married guy for dinner, since I’d obviously helped extract Tammy from her post-divorce funk.

In addition, I assured Tammy that she deserved to go anywhere that her ex went. Including the adult places. As well as do anything that he did. Urging her to worry less about a few wrinkles and more about dressing and acting like the hot MILF and DILF that she was. Highlighting her huge tits and nice ass. As well as acknowledging and appreciating the stares that they gained. Since she was far from an unworthy hag who deserved occasional slut fucking after her ex visited the clubs.

Instead, I further assured her that I would’ve proudly escorted her to the adult places. Rather than being a jealous asshole like her ex. Particularly, since I’d spent years trying to convince my good little Catholic girl wife to let me share her with others. To satisfy her big cock fantasies as well as my collateral bi interests. With my wife repeatedly refusing to let me indulge our mutual interests. Up to and including waving off a couple of incredibly well-hung guys at the last minute. After she’d initially agreed to meet them. Then flirted with them for up to several hours before sending them home with a drooling hard-on, which was incredibly frustrating. To the point where I simply began discreetly seeking some bi fun without her.

Fortunately, Tammy agreed to follow me back to my hotel. Where, despite her noble claims to the contrary, she spread like butter on a hot day. Eagerly first-date fucking me. Resulting in particularly passionate making out. Followed by my spreading her wide and sucking both of her holes inside out. Gladly doing things her ex had refused to do. Ensuring she got off at least a few times before barebacking her pussy to completion. Super-hot honeymoon sex. Followed by lots of additional kissing and after snuggles. Then going down on her again. Thereafter, ensuring she made it home OK and immediately texting, “That was fantastic! When can I see you again?” Clearly communicating that life and sex would be very different and far from boring if she decided to continue seeing me over the next few months.

After our second date, Tammy insisted upon giving me the same swallowing deep-throat head that she used to give her ex. As well as spreading her other cheeks. Explaining that her ex enjoyed repeatedly gaging her before shooting a load down her throat. As well as hearing her, “hurts so good,” beg him to, “hurry up and cum,” while fucking her ass. Then, “making,” her, “blow him back up,” immediately thereafter. So, he could fuck her again. Reportedly glad that I wasn’t nearly as big or rough.

However, despite the apparent complaints, Tammy obviously missed her ex, as well as his big dick, and enjoyed relating such stories. Undoubtedly since she sensed they made me equally hot and horny. Thus, I eagerly listened and at least tried to fuck her nearly as hard. But neither had the sadistic inclination nor equipment needed to make it happen.

Of course, I also related a few stories about helping legally tender young MWM further explore their daddy interests. Particularly stories about first timers. Helping them finally realize their long-repressed bi desires. Proceeding gently and gradually to ensure they thoroughly enjoyed the experience. Or considerably rougher if they wished. However, assuring Tammy that I was bi, rather than gay. Same as her ex whenever he fucked a cub at the club. Which Tammy found hard to believe, but I knew was almost certainly true.

By our fourth date, Tammy began asking if I’d escort her to one of the adult places. Primarily the toy store. Since I’d described using cock-sleeves and vibes with my wife. However, I suspected Tammy truly wanted a full tour. Seeing everything her ex used to see and do before occasionally coming home and fucking her senseless. Likely making her taste another bitch's pussy and ass.

Thus, I selected a particularly notorious club affiliated with a famous men’s magazine in East St. Louis, which had a fully nude strip club and bar on its left side, huge adult toy store in the middle, and maze of video and couple's booths on its right side. Truly a sexual playground.

In particular, like many men, I truly wanted to share my, “woman,” meaning someone who I truly loved and cared about, with another man. Watching him please her in ways that I never could. Listening to her struggle to take him and eventually moan with pleasure. As well as ideally helping him please her and her please him. However, primarily ensuring she got fucked the way she deserved to get fucked. Long and hard. With my blessing and assistance. Feeling incredibly jealous, yet overwhelmingly horny, while watching her spread wide and get plowed balls deep. Feeling nearly as satisfied once she got him off deep in her pussy. And I’d truly begun loving and caring about Tammy.

However, Tammy insisted that she was just curious. Primarily wanting to better understand why her ex visited such places. With no plans or desire to play with anyone else. Regardless, I convinced her to wear a slinky dress over sexy lingerie in case she wanted to visit and play in one of the couple’s booths. Ideally while others watched us fuck through the shared peep holes between adjacent booths. However, if not, no problem. With no pressure or expectations. Truly, as much or little as she wished.

In addition, given my many years of military training, I was well prepared for anything that may or may not happen. Thus, I wore a pair of loose-fitting military-style cargo pants. Thereby, allowing me to discreetly carry ample supplies of condoms, lube, and wipes. As well as a flask of Tammy’s favorite flavored vodka.

“Ready?” I asked Tammy when we arrived in the parking lot of the adult playground. We’d already shared a few beers before leaving. However, I gladly handed her another, since she worried about running into someone she knew. Perhaps even her ex. Making me wonder, “What if we saw her ex?” Would she simply ignore and avoid him, confront and argue with him, or possibly fuck him? Further wondering if I could stand listening to him gag her throat, plow her pussy, and eviscerate her ass again while I patiently waited outside a couple's booth… Or he insisted I join them... And watch him use her like a cum dump… Or help her blow and fuck him as well. Unsure exactly how I'd react.

Finally, I pulled Tammy close and gave her a nice long kiss while cupping one of her big tits. Confirming that her nips were hard as a rock. Meaning, she was obviously more excited than nervous as well as beginning to feel the beers. Then popped open my car door and exclaimed, “Let’s do it!” before proceeding to proudly escort Tammy into the club. Knowing she’d undoubtedly attract lots of attention.

End of Part 1. Part 2 recently posted in Wife Lovers as well.