[MF] Diana(55) and her first anal experience.

If you have read my previous stories regarding Diana you will know we were work colleagues who were friends and then had entered into a friends with benefits relationship. I was 23 years old 6’3, tall and handsome she would say. Diane was 55, about 5’3 chubby with short blonde/greying hair and most importantly huge G-cup breasts, saggy but still full. She was divorced, had two children and was very sexually inexperienced. Her husband had been older than her and a missionary only kind of guy.

After 3 months of being hooking up Diane had tried multiple sex positions, had experienced oral sex, (giving and receiving) for the first time and regularly tit fuck her. (You can read the previous encounters on my profile.)

She was really coming out of her shell. At first when she wanted sex she would say “Do you want to go upstairs” then she started saying to me “I want you to do me” and after about 7 months she would text me. “I’m waiting for you lover, come and fuck me”. She had bought some lingerie (which was slightly too small and her breasts would spill out of). She had a vibrator now and she was getting better at dirty talk. She would call me her toy boy.

The topic of anal sex had come up before, but she said it was dirty and never expressed any further interest. Then about a week before my 24th birthday, I had dropped her off at her house after work.

“I want to do something for your birthday David” she said to me.

“Sure, anything you want” I said. Diane had turned red.

“I want to do it in the bum” she said in a hushed voice. I laughed, which was the wrong thing to do. No one had ever said it like that to me before. I saw her expression and tried to stop giggling.

“You want to try anal?” I asked her.

“Yes, for your birthday…..would you like that?” She said, still embarrassed.

“Yes!” I tried not to sound too eager. “I would love that baby, are you sure?” She liked it when I called her babe or baby.

“I’ve never done it before, and I want to try it. I want to try it with you” she said. I was very flattered and very excited. I had fantasised about fucking Diana’s big, beautiful ass.

“That sounds great baby” I said and kissed her. We went into her house for our usual after work cup of tea followed by quickie in her bed. I went down on her twice and made her cum twice to show I appreciated her present.

Over the next week as my birthday approached I told her how to prepare, I told her how she should wash herself and make sure her ass was clean. I told her she would need her vibrator and I would bring lube and that she might need a few extra pillows. She would ask if it was going to hurt, I said it might at first but I would be gentle. Not to be immodest but I am all in proportion and my cock is on the large side, about 7/5 to 8 inches and quite thick.

Despite all this preparation she still referred to it as “Doing it in the bum” which made me laugh every time.

The day finally came, a Friday night. We were on different shifts that day, she was finished my early afternoon and I finished in the evening. I went straight to her house. She answered the door in her robe but I could see her lingerie underneath. A dark blue silky one piece.

“Happy Birthday!” She said happily and kissed me as soon as I walked inside. She was excited but nervous, I could tell. I hugged her and kissed her back. We both were quite tongue aggressive when it came to our kisses. I loved it.

I expected to sit down and have a drink first but she took my hand immediately led me upstairs to her bed. “I want you to have your present” She said smiling. The bed had extra pillows and a large towel. Her small pink vibrator was there too.

“Are you sure?” I said, again trying not to sound too eager. In response she undid her robe, and stood there, looking sexy as hell, her breasts spilling out of her one piece. She wrapped her arms around me and kissed me. I kissed her back. We did our usual undressing ritual. She would take off my clothes and then I would slowly remover her one piece and kiss down her body as I went, her forehead, her nose, her lips, her chin, her neck, her chest. I would kiss and lick her nipples as I went, I would get on my knees and kiss all the way down to her shaved pussy and kiss it once.

“Get on the bed babe” I tell her. She climbs onto the bed and lays down on the towel. I climb next to her and kiss her and caress her breasts. I play with her nipples and stroke her pussy making her moan sweetly. She kissed me and touched my cock and pulled me closer. We fingered her, felt how wet she was and made her gasp. “Are you ready babe?” I asked. She just nodded in response.

I pulled some of the pillows and put them under her ass to lift her hips up slightly and made sure she was comfortable. I moved between her legs and passed her the vibrator. “We will take it slow Diana” I said.

“Please call me babe” she said smiling.

“Okay babe, use your toy on your pussy while we do this, it will help” I teased her hole with my fingers gently. “How does that feel babe?” I asked

“Feels funny” She said “It tickles”. I reached for the lube and squirted it on my fingers. I made sure they were covered. (You can never have too much lube for anal).

“Okay, I’m just going to try my finger” I told her. I placed it on her entrance, she shivered.

“Its cold!” she said.

“Sorry” I said grinning. “Here it goes” I slowly pushed my finger inside her ass. “How does that feel babe?”

“Its okay, its cold and weird.” I pushed a bit further.

“Does it hurt?” I asked. I kept pushing.

“No, feels like I need the bathroom” She laughed. “Feels dirty” she said mischievously.

“Okay babe, we’ll try two fingers” I removed my finger, put more lube on them and then tried to push two fingers inside her ass.

“Ugh ow” she gasped. I stopped. “That hurt”

“Sorry babe, I’ll go slower.” I very slowly started to move my fingers backwards and forwards letting her get used to the feeling. “Use your toy” I said.

“Okay….” Diana said and started massaging her pussy with the vibrator. Her other hand went to breast involuntary. She enjoyed squeezing them herself especially when I was watching.

“Do you want to try my cock babe” I asked after she got used to my fingers. She nodded, looking at my erection was seemed huge compared to her tight hole. “Are you sure?” I asked again.

“Yes….David I want this” she said looking me in the eye.

“Okay” I said, I massaged some more lube into her hole then rubbed it all over my cock. “Okay babe, try and relax. Use your toy. If you want me to stop…say stop, okay?” She nodded.

I put the tip of my cock on her hole and began to push. I noticed she gripped the towel with her free hand. “Relax baby” I said “Just breath out” She did and I felt her relax and my cock head popped inside her ass.

“OW! Stop stop stop!” She cried out. I froze and didn’t move. We were both still for a few minutes but she kept using the vibrator.

“Want me to pull out?” I asked.

“No….just…wait.” She said. “Just go slow” I went as slow as I could I pushed inch by excruciating inch inside her. She was so tight, I wanted to fuck her hard and be all the way inside but I couldn’t so I took it so slow. “Slow down….oh it hurts baby” she would say. I would offer to pull out but she would always decline. “No its okay, keep going” It seemed to take forever but eventually all 8 inches were inside her. She breathed out “It’s so big… I feel so full”

I leaned over and kissed her, I kissed her breasts. I moved my hands all over her. When she started to relax and I pulled back a little and moved forward again, gentle slow thrusts. I could feel the vibrations from her toy.

“Is that okay?” I asked.

“Uh huh” She moaned.

“Do you want me to go a bit faster?”

“Uh huh” she moaned again. I started to move faster and pull back further. Occasionally I would go too fast and she would gasp or cry out but quickly “It’s alright, keep going lover”

“Does it feel good babe” I asked after we got a steady rhythm. I was thrusting deeper and faster now.

“Ugh yes….I like it….” She had wrapped her legs around my hips. “Keep doing it” She was rubbing her clit herself now, not using her toy anymore and squeezing her huge tits.

We fucked like this for a while, I wanted to fuck her harder and faster but I didn’t want to hurt her.

“Where’s my cock babe?” I asked, I loved to tease her and make her say it. Make her talk dirty.

“Inside me…oh….ah….” She moaned. I would slow down in response and repeat the question. “It’s in me” she said. I almost stopped completely and asked again. “Its in my arse” She said eventually. I resumed fucking her again and started getting louder.

“You like my young cock babe? I asked.

“Yes….I like it” she said.

“You liked being fucked by your toyboy” I asked.

“Yes I love it….please don’t stop” she moaned.

“Do you like my cock in your arse babe” I asked. She didn’t respond so I asked louder. “Say it”

“So….ah….naughty….ah….I love it….” She said “I love your cock in my arse”. I loved hearing her talk dirty. Her accent made it sound so sexy.

“Cum for me babe” I said to her as she rubbed herself furiously. “Cum with my big cock in your arse”. She did cum, I felt her whole body shake. I was so close myself. “Can I cum in your arse Diana?” I asked. “Tell me”

“Cum in me….cum in meee” She moaned and I did. I came inside her, I filled her 55 year old virgin arse.

We cleaned up afterwards. We rested for a while and then I did go down on her and made her cum again using my tongue. She was a little too sore to do much the next day.

We didn’t do anal again for another month but after that it became more regular. She really liked it, made her feel dirty and she liked the feeling.

Thanks for reading, as usual please feel free to AMA or check out my other stories.

Source: reddit.com/r/gonewildstories/comments/10cytk9/mf_diana55_and_her_first_anal_experience