Had One Last Single Run.. The 24 Year Old MILF [MF] | 2016

So about two years ago I ended a 5 year relationship and had a 4 month period on Christian Mingle that to my surprise ended up as one of the best runs of my life. Since that single run has now ended figured I would share the highlights for your consideration.

Shelly was the first girl I ever messaged on the first night. She was exactly my type from her profile pictures. She was a 24 year old petite natural blonde with a super cute face and green eyes.

There was a lot to the back story so I will simplify with chronological bullet points for sake of time: - Hit it off and had a couple dinner dates - Would text and get flirty but would not get sexual - Called crying and apologized for not being up front. Revealed she was a single mother of 2 and her divorce wasn't even technically final. - Got knocked up as a Freshman in college. Didn't come back to school. Had a quick wedding. Didn't care for her husband but they had a BC accident and had daughter #2. Filed for divorce because he was a bad parent. - She lost her self confidence and joined not looking for anything but adoration.

We had agreed to go our separate ways as friends but she asked a favor of me. Her cousin was getting married and she didn't want to go alone to the wedding. I set boundaries but agreed. he wedding was pretty lame with the same ole DJ playing the same ole songs you always hear. Very few people danced and we sat at the table drinking. She kept commenting how she never drinks anymore and how she was feeling a buzz. She became closer to me and began touching my leg..she complimented me no less than 5 times how good I looked and how good my cologne smelled.

It was starting to wind down when she pulled me near so she could whisper, "If I tell you this will you not freak out? I am cool with this being the last time we hang out. I got a hotel room though because I knew we would drink. Do you want to stay with me?"

By this time I had a little buzz too and she looked phenomenal in her sherbet colored cocktail dress. I'll also be honest. I am a man and I would lie if I didn't say the reason I went was the outside hope I could get some action. That's why all straight men go as wedding dates. Still the red flags wove so I qualified her more.

"Here's the deal. You know where I stand and if we are both in bed and I have been drinking I am going to make a move. I clearly am attracted to you and want you.. but just know.. it is what it is." Clearly 5 years of being with the same girl had made me a smooth talker (Sarcasm).

Luckily for me I would later find out she had not had sex in over a year..before the divorce. She was desperate for affection and needed to feel wanted and even my cumbersome tongue couldn't mess it up.

"It'll be our secret. One time thing.", she said and gave a sneaky little grin. The entire mood changed after that for us. She began rubbing my leg more and made me dance to the slow songs with her. We drank some more and as the reception started to wind down she let me know it was time.

"I lose my filter when I am drunk so don't hold it against me. ", she started. "We need to go soon or else I am going to take you into the bathroom and suck your cock." Suffice to say we gathered our stuff and went to the car. The Hampton Inn was maybe two miles away but I had to find a drug store first for condoms.

I am going to brag a little. I know most guys do some humble brag where they talk about being "bigger than normal" or "told they are big".. I will freely admit I am blessed with a big cock. I literally HAVE to wear Magnums because I had a couple scares in college when I used the infirmary condom and had unfortunate breaks a couple times that caused a tense month after. I say this because there was NO way I was about to risk that with a girl who had already had two "oops" babies.

As we stepped into the elevator I asked, "Still craving doing what you said at the wedding?" She just smiled and said "We'll See"

The second we got inside our room and turned the light on she instantly hit the floor and attacked the belt and zipper of my slacks. From just mentioning it in the elevator I was already about 75% hard and she wasted no time bringing me to 100%. I used one hand to help guide her up and down and the other to pull her hair back. In the back of my mind I still worried about whether she would mistake this for "love making" so I consciously began making sure she knew this was about fucking. I began talking dirty.

"You have been needing my dick all night" "I am so much bigger than your ex-husband, ain't I?" "You turn into a dirty little slut when you drink"

As far as I would go she loved it even more. Soon she would take me out of her mouth to respond. As I continued she soon began telling me how bad she needed me inside her, how wet she was, and how she couldn't wait to fuck me.

I teased her a little more, "You want this inside you? Ask for it" "I want you to fuck me", she responded. "Say please like a good girl", I remarked. "Please" "No! Say please and then ask for it" "Will you please fuck me?", she said. About this time I was literally shaking with adrenaline. It had been 5 years since I had been with anyone besides my ex ad the sight of Shelly's cute face bobbing on my cock and begging to get fucked had me ready to go.

I nudged her up with my hand and carried her to the edge of the bed. She took off her heels and I pulled down a neon yellow thong. I began gently dipping into her wet slit and round her lips. Trying to stay into character of being dominant I asked,

"You ready to get fucked like you have been needing? Turn around and give me that ass right here."

She quickly moved onto all fours and I lifted her dress over her perfect little round ass. I could see the wetness of her pussy as it had even dripped onto the inside of her leg. I sank two fingers inside her and she pushed back onto my hand. I got on my knees and angled beneath her to lick her clit while fumbling to get my pants off my ankles. I had to get inside her. My dick still sticky with a mixture of her saliva and my pre-cum.

I stood up and grabbed the CVS bag and ripped through the plastic around the condom box. I was literally shaking with adrenaline and couldn't open the wrapper. I had to tear it open with my teeth. I positioned myself behind her and slipped my cock into the wetness of her lips moving it to create lube around the head . I pushed her back down and adjusted her ass to create the perfect angle and sank just inside her. Caught up in the moment I put my full cock into her in one single thrust.

"Fuuuucccckkkk. Hold on!" she muttered it obvious pain. I broke character to ask if she was alright and if she wanted me to pull out. I now was easing back and forth slowly. She didn't respond.

"Shell.. you ok? Need me to hold up?" "K. Don't. Im Good. God it feels good" she stammered in broken English "How you want me to fuck you?", I asked. "Just fuck me. Fuck me."

I quickly resumed pace until I was pounding into her harder than I think I have ever fucked someone. Her ass bounced in rhythm to each thrust. I smacked her ass, I would pull her had back, a steady stream of dirty talk and questions flowing from my mouth which she only responded to with screams and pants at first. I knew I was nowhere close to cumming as I was too hyped up. My thighs twitched and my cock throbbed.

I flipped her over and lifted her legs against my stomach and chest and began pounding again. She pulled down her dress straps and her breasts began bouncing in tune trying to free themselves from the fabric. I crossed her heels over and began thrusting slower but deeper. Turning my hips at the deepest point. Shelly was the loudest fuck I have ever had. She was an uncontrollable stream of screams, cries, "Shit's", "Fuck's", "God's" and incoherent babble. She would routinely wrap her legs around my lower back and pull me close digging her nails in my shoulders.

Finally I was spent and not even close to cumming. I pulled out and crawled into the bed and lay there catching my breathe. She couldn't move from the foot of the bed. Still halfway in her dress..panting and otherwise motionless. In my mind I questioned myself thinking I had quit. She finally mustered energy and sat up..peeling her dress off finally revealing ample C or maybe even D cups on her tiny frame that may have been 110 pounds.

"Damn Shell...your tits are amazing. If I knew that I would have taken that dress off at the start! ", she smiled bashfully and said "One gift from being a mom..they grew and stayed". She went to the bath room.

Still self conscious about quitting I still lay there a bit upset, then Shelly surprised and confused me by saying from the bathroom,

"I have never did that before. Wow."

"Did what?", I questioned.

"Never had multiples.. I hardly ever came as it was."

Apparently she had numerous orgasms one after another and each time she wrapped her legs was a different one. This turned me on again. I was back to full attention when she came back out and she noticed.

"Holy shit that thing looks huge. Didn't you cum?"

I explained how I was so amped up I couldn't. She straddled me and tried to ride me but we couldn't get it in her and she was too tender now. "I want you to cum too". She peeled the condom off and began going down on me. I was super sensitive to the point it almost hurt when she would work over the tip. I bit my lips and tried to withstand it.

"I want to see you cum", she whispered. "it's your turn."

"Where do you want me to cum?", I asked.

"Anywhere you like babe".

I was closer but not there and the sensation was too much. I rolled her off and stood on my knees over her on the bed. I began jacking myself furiously. She squeezed her tits and stared at my cock saying, "Cum on these? You like them so cum on them. Please cum on me."

That was it... my cock exploded with a thick, chunky load had built up for three days. Lost in the moment I didn't even aim. When I looked down the majority of my load had hit her jaw and right chin. Some dotted her neck and collarbone. I was worried she would be upset

"That was so hot! I think it's in my hair though.", is all she said. I retrieved a wash cloth. After clearing her skin we showered together.

We woke up the next morning and had a much more subdued encore. She rode me and I would periodically thrust up into her. This time I had no problem reaching climax and filled the condom. We kept true to our word and that was the last time we saw each other aside from some texting. We both got exactly what we needed. She felt wanted and I let 5 years of frustration out onto her face. With my knew confidence I sat out for more conquests.