I have been a SD off and on for about 10 years or so. A the time of this story I had been seeing my first SB for about a year, since she graduated from my senior seminar class… read the story how it started HERE. We started our arrangement right after my birthday in May so we were coming up on both my birthday and our year anniversary. Also, I knew she was leaving over the summer for graduate school, so our meetings had become more intense for both of us as we saw the end in sight.
Anyway, baby had asked if I wanted anything special for my birthday present and honestly, she would do whatever I wanted, so I had to really think about it. Little did I know it would turn into a bit of a small obsession for me after that. I asked her to worship my cock and see how many times she could make me cum in an afternoon. We usually spent a few hours in a hotel together and I would cum once or twice. I love to make the first one last with being edged, a variety of positions and my attention to her orgasms, etc.
She accepted the challenge enthusiastically. I am 99% of the time dominant in the bedroom, so after I greeted her in the hotel room I instructed her to take her clothes off, to give Daddy a little inspection. Then I told her if she could make me cum 3 times I would do whatever she wanted next meeting. She immediately dropped to her knees and after getting my pants off and sitting me in a chair, she proceeded to rim me quite aggressively. We had discovered over the past year how much I liked this and her plan clearly was to get me to cum fast the first time.
It worked. she rimmed and deep throated me with an enthusiastic energy bordering desperation, it was intoxicating. switching from cock to my ass with stops at my balls for variety she got cum on her face in about 5 minutes after getting to the hotel room.
According to some studies, 18-year-old males have a refractory period of about 15 minutes, while those in their 70s take about 20 hours, with the average for all men being approximately half an hour. At the time I was 40 and just like now, after the first orgasm, if I keep going I can stay hard throughout the refractory period. It’s actually kind of amazing how it feels both pleasurable and a bit numb for 10 to 15 minutes.
She didn’t even clean all the cum off her face before putting a condom on me and climbing on. Riding me hard in a chair it was about 15 minutes later when I felt I was completely ready again. I let her know this and she climbed off, asked me to get on all fours at the edge of the bed then proceeded to suck my cock, balls and ass from behind. Hands down, this is one of my favorite positions. Why does if feel better? I have no idea. But it does. She did this for what seemed like forever, in reality was probably only 1/2 hour. Which is as we all know, a long time to suck something! I remember feeling close to the edge for awhile. A feeling women talk about a lot, the cliff before the orgasm.
One thing I love about cumming multiple times is that the 2nd one is intense in a very different way. The first one is sort of a mind blowing intensity of pent up feeling and sensation, one that I usually try to not let happen too soon. The second one takes a long, slow climb up the cliff… and then Blammo! Often and to my surprise I usually shoot more cum than the first one. It is always more watery but it is also counter intuitive how it is more. The feeling is so overwhelming that I usually have to make sure nobody touches my cock for a bit after cumming that second time.
Long story short, I came that second time with a blinding light in my mind. She was still behind me licking my ass, balls and sucking my cock, and she opened her mouth and drank it all. Then she let go of me and asked, “Daddy, I know you need to rest a bit now. I am going to take a shower then if you are ok with it, sit on your face so I can rest my mouth and cum.”
Of course I agreed to this plan. We were about 1 hour into our rendezvous and I was on track for 3 orgasms for sure.
Baby climbed up onto my face after her shower, her pussy both wet with water and slippery from her excitement. She was really getting off on being more assertive than usual. Her big labia swollen from excitement she rode me gingerly at first but when I started slapping her ass she got more aggressive. She came Hard and quivered and shook on my face, her legs trembling. She was So Loud and I often wondered what the hotel thought, if they ever got complaints… I mean, she was always so fucking loud. It was such a turn on.
She had ridden me for some time and when she finally climbed off I was at about half mast;) My cock was excited if not a little tired, but she wasted no time in taking me all in her mouth and slowly, deeply and with great messiness, sucked me hard once again. At this point, keeping me hard took constant movement, friction, sucking, etc. I decided to give her a break in decision making and took control. I put her ass up, head down and began slowly but steadily fucking her doggy. After awhile she decided to take a little control back and asked me to put my cock in her ass. Of course I obliged. Who could resist? She was a gorgeous 22 year old petite woman with nice perky tits and an Insanely wonderful ass… and the aforementioned outtie pussy;)
Well, I wasted no time and I got my cock in her ass with minimal effort. She became louder than ever with her particular moaning, high pitched yelp. Fucking amazing. I now understood her plan. And sure enough, she soon asked me to remove the condom and cum in her ass. I practically came as she asked me that. A side note. Having been together for a year, we had talked about this a few times. We wore condoms for sex because although we were both tested, we both had other partners. We had both just gotten a new round of testing done… so we were embolden to play out this fantasy of hers, getting an anal cream pie. Something up to that point she had not experienced. I remember ripping the condom off and throwing it, then slowly pressing the tip of my cock into her ass until I was balls deep. I slowly started fucking her and came almost immediately. Grabbing my camera, a frequent object of our desire, I documented the cum dripping from her ass.
So did number 4 happen? Yes, hence this story! It is one of the few times I have cum 4 times in a day, let alone in a manor of hours. The details of number four were as follows… We both showered again and ordered room service. We caught up on each other’s lives for at this point, we talked about everything. I remember a lot of it centered around her anxiety about moving for school in the fall. We never talked about continuing long distance, both knowing it was what it was. That said, over the last 10 years, I have fucked her a half dozen times while she visits her family in NY. I am her guaranteed hookup:). I feel very honored.
Number 4. Not gonna lie, number 4 took awhile but she was determined. And because of that, I didn’t feel bad that it took her a long time to suck out number 4. I finally came fucking her face pretty hard and fast. It was messy and wonderful and utterly exhausting. I actually took the following day off and didn’t do anything.
I will never forget this experience and think of it often. She reminds me of it sometimes when I see her on her visits. Cumming 3 times now at the age of 50 is a feat for me but I do manage it frequently. 4 I think would take me 24 hours;)
I hope you enjoyed my trip down memory lane. Next story will feature my birthday sexy time with my current 19 year old sugar baby… stay tuned.
Source: reddit.com/r/gonewildstories/comments/nersp9/mf_happy_birthday_sugar_baby