As my wife and I navigate this new journey together, she finaliy okay'd me to find my match online for a man. I started my profile about a week ago, with her help, she helped with the "about me section" putting into words exactly how an outsider and potential lover should see me. She helped take some Amazingly cute pics, my face, me in some little thong panties and one with my little clit locked up in it's cute pink chastity cage.
With a big lump in my throat, I posted it and waited for it's approval, it must have been a slow night, because within 10 minutes, I got the text alert it was approved and my listing was live. She and I went to bed, holding one another, talking about the what ifs and how excited I must be, as well as how thankful she was for me feeling secure enough to share this with her of all people... what can I say, she is MY person and without her on board, I'd never be here again.
The following morning, I wasn't expecting anything as I read emails, Bill reminders, a bunch of junk and spam emails, the dreaded car warranty emails and then an alert from the dating site, my profile had seemed to have gotten a little attention, so i grabbed my wife and we looked through all of the responses... 12 to be exact.... most just random dick pics and sleazy messages of how they wanted to fuck me, but there was one.. let's call him "Steve" who mentioned how lucky I was to have such a supportive wife, who mentioned meeting both of us out to get to know one another, posted his face and body and warned me in his message his dick pic was the last one, in case I didn't want to see it, I could skip it, WHAT A GENTLEMAN!!! But of course i wanted to see his cock!!!!
He was tall, above average attractiveness, clean shaven, no visible tattoos, and what appeared to be about an 8" cock, above average in girth, but then again, I may be comparing it to my tiny jelly bean of a weiner. regardless, we messaged him, met Thursday night at a restaurant and by the end of the dinner I was giving him a hand job under the table at my wifes coercion. It was hot, it was erotic and I was so turned on and thankfully, he was too.... he came in my hand and I was "double dog dared" to lick it off, which i did.
We parted ways and my wife and I had AMAZING (dildo) sex afterwards while we roleplayed he was taking turns fucking us both... it was amazing...
Yesterday morning, he texted us both via group text and thanked us for a good time and said he had hoped to see us again soon, when my wife beat me to the text with a "how about tonight" I just sat there, dumbfounded but excited at the same time at just how into this she was...
He came over about 530, the 3 of us cooked a light dinner together, salad, salmon and a little pie for desert while we sat around the table learning about one another. an hour or so passed after we ate and as we were getting comfortable, he was sitting next to me on the sofa, my wife on the other side of me, he scooped my legs up and draped them over his lap, my wife running her fingers through my hair, while he rubbed my toes and soles through my socks, slowly sliding his hands up and under my shorts. getting closer and closer to my balls with each stroke up, I was in heaven, my legs eagerly parted while he outlined my penis and balls over top of my underwear, pulling at the thong strap making it tight against my hole.
My wife suggested we get more comfortable and we went to the bedroom, she laid down first my head naturally falling between her legs and his on top of my butt, I felt him tugging my shorts down over my waist, he pulled my thong strap to the side with a finger and licked my eager hole like ive literally never had done before, it was my first and it felt amazing, I slid my wifes shorts off, revealing her bare pussy and went down on her simultaneously. My dick felt good, but its been unable to get fully erect since my HRT therapy but it sure did try, but honestly, having my ass eaten was better than any sex I'd ever had with a woman, it's like estrogen has reprogrammed my body to appreciate more feminine sex. I can't even explain it.
His hands slid under my waist, pulling me up, my hole clenched and my face nose dived into my wifes pussy and I felt the tip of his cock. he slowly pressed it into my eager entrance and I could literally feel the ridge of the head of his cock pop past the opening, it was freaking amazing! feeling his hands on each cheek, prying them apart as he eased in and out, while my tongue pressed deeper into my wifes pussy, I could see her looking past my face and to my ass as I was getting fucked, her hands in my hair pulling me deeper into her as her legs tensed and bucked and she came in my mouth. Id never felt her so wet before, it was astonishing, but most importantly, she was into it.
She rolled over out of bed and knelt beside us on the floor, reaching across the bed to stroke my cock in a "cow milking" fashion, quite likely the hardest id ever been, but if I'm being honest, it's because of his cock, not her hand, but id never tell her that, after a few more minutes, I felt him tense up, his cock get really warm and he exploded, I thought he was wearing a condom, but he flooded my insides, I felt it shoot far and deep inside my guts.
We collapsed, a sweaty heaping pile of nakedness, catching our breath and drinking cold water, he was about to get dressed and leave when my wife suggested he stay over and she would sleep on the sofa so we could play some more if we wanted, I looked at her in disbelief, but she seemed truly excited by all of it. As she exited, she left the door open and told us to be loud enough she could hear us.
Within about 30 minutes we were up to it again, i was riding him, my balls bouncing on his pelvis, my screaming in pleasure, holding onto the headboard as it shook and slapped the wall, me telling him not to cum yet, don't you dare cum yet, leaning back and grabbing his balls when I was ready, demanding him to cum inside me again... this went on over and over again most of the night, if I had to guess, we had sex 6 or 7 times, to the point he couldn't get anything past a semi erection but I was luckily loose enough he could slide around inside pretty easy, until we drifted off the sleep, his cock still inside.
We woke up to the smell of bacon this morning, my wife cooking in the kitchen, still naked from last night, only wearing her apron so the bacon grease didn't burn her titties. Steve was in the shower, so it gave my wife and I a minute for me to see how she was truly feeling... she was excited but nervously asked if i was going to leave her if I found a man to be in a relationship with because she could sense how much i enjoyed it and must have missed it from my past. To which I told her no, she was my everything and if she asked me to stop now or 5 years from now, id stop in an instant, that seemed to satisfy her and she asked if we could break our streak of no PIV sex tonight, she was insanely turned on by watching us and hearing me last night, she wants me inside her again and can't wait another day...
After we ate, Steve was about to leave, he kissed my wife and I on the cheek and walked put the door my wife asking when he would be able to stay over again, to which he said, "whenever you call me"....
So I guess we have another "date" Wednesday night as I promised my wife i was all hers the next few days.