First time anal with a long time girlfriend [MF]

During my final year in college, I met and began dating Jackie. She and I hit it off immediately. We were into the same bands and movies, and shared a similar sense of humor. It also helped that she was adorable. She was 5’4″ 120 lbs. Dark shoulder length hair and hazel eyes. She had some curves too. Only a 34B up top, but her ass was PHAT! I grabbed at it every chance I could, and she would tease me relentlessly with it too.

Once we graduated college, we found jobs in the same area and got an apartment together. Most mornings and weekends were spent lounging around where she would be in a t-shirt and a thong, wiggling her ass around trying to get me riled up. Most times it worked for sure. I was always 100% honest about my desire to fuck her in the ass, but she would always say “I’m sorry, baby. No.”

As we continued to live together, our sex lives grew adventurous. We introduced various toys and lubes into our bed and explored different positions and things that turned us on. Come to find out, Jackie was totally into light anal play. It became a regular thing where she would be riding me on top, and I would have one finger knuckle deep in her ass. And every time we did that, she would instantaneously cum. Anytime I mentioned this fact, she would respond with “It’s just a finger. Your cock is way bigger!” Bummer.

During the spring time we decided to take a small vacation to a local beach town. We drove in that morning and did all the fun touristy things like shopping, visiting the aquarium, walking along the beach, etc.. After the sun had set, we checked into our hotel near the downtown area and got ready to head out to dinner. The hotel was gorgeous. Our room had a king-size bed, mini-fridge, large shower, hot tub, the works!

As soon as we got in the door, Jackie stripped down to nothing and headed for the shower. I poured myself a glass of wine from the bottle we had bought at a tasting room earlier, and put the complementary champagne the hotel gave us into the fridge to chill. After my glass of wine, I decided to be a bit naughty. I stripped down naked and headed into the bathroom. I opened the shower door. “What are you doing?” Jackie asked with a smirk. I didn’t say a word, I just dropped down to my knees and took her clit into my mouth. I sucked and licked a bit. “Hey!” she cried as she lost her balance a little bit. I caught her by gripping her ass cheeks and pushed her clit tighter against my lips. I detached and slid my tongue from the bottom of her pussy (near her ass) to the clit a few times. I stood up, smacked her ass, and then exited the shower to dry off.

After she finished her shower, she came out asking what the hell that was about. I told her it was just a preview of what was to come. We got dressed and headed to dinner. After some good food and strong martinis, we stumbled back to the hotel room. We had barely closed the door to the room when the clothes were coming off and flinging everywhere. Our lips locked tight against each other as our hands roamed. I found her pussy soaking wet to the touch while her tiny hands gripped around my rock hard cock.

She pushed me on to the bed, dropped to her knees, and consumed my dick. When we first started dating, she was a below average cock sucker. But recently she had improved with some tips from me. She ran her lips up the sides of my shaft, stopping at the top each time to swirl her tongue around my head. I let her know she was doing an incredible job by moaning her name.

After a couple of minutes she stood up with a huge smile and kissed me again. I wrapped my arms around her and rolled her over on to the bed. I spread her legs wide open and dove in to her pussy. I continued where I left off earlier in the shower by licking her slit from bottom to top, pausing at the clit to suck on it a bit. I paused to find our “sex bag” as we called it. Inside were the toys, cock rings, and lubes that had become a regular part of our sexy times. I pulled out the medium-sized blue vibrator and guided it into your aching pussy. I turned it on while I latched back on to her clit with my lips. She was soon wiggling around yelling “FUCK that feels so good!”

After a few minutes of this, she gasps “Get up here and fuck me!” I remove the vibrator, turn it off, and toss to the side. With her on the edge of the bed still spread eagle, I aimed by precum-covered cock into her. I slid in with ease due to her insane amount of juices and begin fucking her hard. I grab her thighs and thrust in and out with enthusiasm as her eyes roll back in her head. I could tell she wanted to cum, but she usually only did when she was riding me on top. So I suggested a position change.

I laid down on the bed on my back while she mounted me. Almost immediately she drove her pussy down hard on my and grinded back and forth on my cock. She loved feeling me deep where my cock slid against her g-spot. My hand roamed to her asshole where I slid a finger in using her juices as lube. She leaned down and whispered “You love playing with my ass, don’t you?” All I could say was “Uh-hu.” Then she asked the unexpected… “Grab the lube. I want you to fuck my ass.”

I nearly threw her across the room in an effort to get the lube before she changed her mind. I told her to lay on her back while I poured the lube into my hand. I rubbed it all over my dick, then I poured more to lube her ass. I slid a finger in too for extra measure. With her legs in the air, I positioned my cock against her ass. I told her to let me know if it became too painful.

I pushed gently until the entire head of my cock disappeared into her ass. I paused to ask her it she was okay. She confirmed that it was a bit uncomfortable, but she was doing fine and to continue. I pushed in a bit further. I could see a bit of pain on her face, so I pull out a bit and squeezed a bit more lube. That seemed to do the trick as the next inch of my cock seemed to go a lot easier. Before long half my cock was in her ass, and I was beginning to realize that I was fucking my girlfriend in the ass. I knew that once I started pumping, I was NOT going to last long. A minute or so later, I fully in her ass. Her eyes were closed and she was moaning, which I knew meant she was enjoying it.

I pumped in and out slowly to make sure she was okay with it. Once I saw the pleasure on her face, I slid my hands down to her pussy and rubbed her clit while I fucked her ass. This sent her into a bit of a frenzy. She writhed around and just kept muttering “Oh god. Oh god. Oh god.” After a bit more than 30 seconds of that, she fucking shuddered and yelled “I’m cumming!” Her climax ignited mine. My cock stiffened and pulsed deep in her ass. My load filled her as she came down from her orgasm. Spurt after spurt filled her ass until I collapsed on top of her.

We got up and cleaned up. We celebrated by finishing a bottle of champagne and passing out. In the morning, I asked her if she would ever do it again. Unfortunately, she said she was so sore that she didn’t think it could ever happen again. While I was sad, I was still happy that it happened at all.

Source: reddit.com/r/gonewildstories/comments/9tf9ru/first_time_anal_with_a_long_time_girlfriend_mf

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