This is a true story that took place in 2008.
I got divorced from my first wife in 2007 and went through a bit of a dry spell afterwards. I had a brief fling for a few weeks with a nurse that I knew from work, but she had a boyfriend and we cut our relationship short after just a few hot weeks of messing around. After that, it was just porn and masturbation until early 2008.
I’d started hanging around with a couple of women I worked with. Both were older than me – at that time, I was 28 while they were 35 and 38. The 35-year-old, Tommie Ann, was a bigger girl, but she had a great personality and huge breasts that would push against whatever she was wearing. The 38-year-old, Beth, was a cute blonde who had a boyfriend but would come to the movies with us and do other fun stuff when he was at work.
To be honest, I wasn’t physically attracted to either of them, although looking back it’s clear that Tommie Ann was making suggestive comments about us fucking. One time, when we were all at her house watching a movie and eating pizza, she changed into her pj’s and made a comment about how we should all just go into her bedroom and have some fun together. Beth looked a little disturbed at the thought, and I just dismissed it as a joke.
Tommie Ann would call me a lot, so I’d usually hear from her every day. During our phone conversations, I found out that she had had many threesomes, had slept with both her ex-husband and his brother, and had at one point been a phone sex operator. It wasn’t long before thoughts of Tommie Ann would pop into my head while I masturbated, and I used to fantasize about fucking her and cumming inside her. In my head, I didn’t want a relationship, just a good fuck session.
Anyway, one day Tommie Ann came over to my apartment, and we watched a movie and ordered some Mexican food. The movie finished quite late. I was getting really sleepy, as was Tommie Ann. When the movie was over, she asked if she could crash on the couch. I agreed and went to bed. I couldn’t sleep, though, and found myself getting really horny. Sex had not been on my mind earlier, but it sure as hell was now. I pulled off my boxers and threw them on the floor. Naked, I let my hands roam over my body and I started to pull on my dick.
I’ve always been good at prolonging my masturbation sessions, so I pleasured myself for quite a while, thinking about how Tommie Ann was sleeping right through the wall. I then decided to do something risky and go to the bathroom naked. I didn’t need to go to the bathroom, but I was turned on at the thought of getting caught.
Quietly, I got up, went to the bedroom door, and slowly opened it. The apartment was in almost complete darkness, but not so dark that you couldn’t make out the outlines of the furniture. I listened for a moment and heard Tommie Ann breathing deeply. It was the deep, regular breathing of someone fast asleep. Convinced she was actually sleeping, instead of going to the bathroom, I crept out into the living room. I could see her outline lying on the sofa, partially covered in a blanket I’d given her. She definitely seemed to be asleep, so I crept closer.
My penis was fully erect and throbbing painfully. I approached the sofa, and saw that Tommie Ann was lying on her back with her eyes closed. I reached the sofa and positioned myself between the coffee table and Tommie Ann, standing over her, completely naked and erect. Slowly, I started to play with myself, and lowered myself down so my hard cock was almost touching her face.
I could feel her breath on the tip of my dick, and it felt amazing. It was warm and send an amazing tingling sensation throughout my whole body. I continued to stroke myself, slowly at first, but then increasing in speed and intensity, and it wasn’t long, despite my masturbation stamina, before I could feel my climax building. I kept stroking furiously as long as I dared and then twisted slightly as I started to spurt stream after stream of cum, out of my dick and onto the blanket covering Tommie Ann. She didn’t move, didn’t wake up, and as I stood up properly to return to the bedroom, a last piece of cum dripped out of my dick and landed on her right forearm, just above the wrist.
I froze, thinking she’d move, but she didn’t. I retreated to the bedroom. I couldn’t believe what I’d just done, couldn’t believe my cum had actually gotten on my sleeping friend, and I was amazed that I’d done something so risky without getting caught.
That’s as far as things went that night – when I woke up in the morning, Tommie Ann was gone, the blanket neatly folded and a “thank you” message written on the little fridge white board. I thought about what I’d done the night before and knew that I wanted more.
About two weeks later, it was Tommie Ann’s birthday. She was having a party with some friends and family, and I was invited, but due to work I couldn’t attend. I always like to get people stuff on their birthday, so I asked her what she wanted and she just shrugged and said she’d think about it and let me know.
A few days later, I got a phone call from her when I arrived home after work.
“I’ve thought about what I want for my birthday, and I know what it is,” she said.
“Oh, year?” I answered.
“Yeah,” she said. “I want you to fuck me.”
The request hung in the air for a moment. I wasn’t used to women being that direct, so I was a little shocked.
“Sorry, you want what now?” I asked.
“I want you to fuck me. Make love to me. Don’t say you haven’t thought about it,” she said.
I was speechless, and said something along the lines of, “Well, yeah … no … I mean … what … huh?”
She laughed on the other end of the line. “This will be strictly a sex thing. I know you’re not into me, and I don’t want to date a younger guy, but I do want to fuck you. Neither of us is getting any sex right now, so why shouldn’t we help each other out?”
My heart was pounding in my chest. “Well, yeah, ok.”
“Great,” she said. “You can decide when and let me know. See ya!” And just like that, she hung up.
I looked at the phone and remember smirking. Damn, I thought to myself. This could be fun!
The following Friday, I invited Tommie Ann over to watch a movie. I have no recollection to this day of what movie it was. All I could think about was the fact I was going to fuck her, and it was up to me to decide when. I wanted it to be that night, but she’d not mentioned sex to me since the call earlier in the week.
The movie ended, and I fidgeted nervously.
“Well, I’m kinda tired,” she said, stretching. “I guess I should go home.”
“You can sleep here again if you want,” I said.
She looked at me sideways. “Sure,” she said. “Will it be here on the sofa, or …”
Her words hung in the air.
Trying to be confident, I said, “You wanted me as your birthday present, let’s go in the bedroom and have sex.” Boy, I must have sounded ridiculous, but I hadn’t had sex in months and I was horny as hell.
With that, I got up and motioned for her to follow me. She followed me into the bedroom, and I closed the door. The bedroom was a lot darker than the living room.
Unromantically, I said, “Ok, take off your clothes,” as I started to strip myself. I was naked first, but couldn’t see much in the room, so I felt my way to the bed. It was a queen size pushed up against one of the bedroom walls. I crawled over to the side of the bed near the wall and heard the sound of Tommie Ann getting naked. I could hear her breathing and could tell she was a little nervous.
I saw her outline get onto the bed. I laid on my back, she laid on her left side, facing me.
“What do you like?” she asked.
“It’s your birthday, you do what you like,” I replied.
With that, I felt her hand slowly touch my chest. I breathed in sharply, and felt her soft touch trace around my chest and slowly move down, over my stomach, lowering slowly and gently to my groin, and then slowly running her fingers over my penis, which was hardening.
She teased it for a few moments, feeling it harden.
“You’re a good size, and really thick,” she commented.
I didn’t answer, because it was at that point that she grasped my penis firmly in her hand and began to work it back and forth. I let out a slight groan, savoring the touch of a female, and enjoying every moment.
She worked my dick for a good 5 minutes, gently and slowly but steadily. I then saw her lower her head and I felt the tip of her tongue flick out and touch the tiop of my cock. That sent shivers through my whole body. She teased and licked the shaft and tip for a few moments, before covering the head with her mouth and taking all of me inside her mouth, slowly at first, then faster. I could feel her tongue swirling around the penis tip furiously. I began to pump my dick in her mouth in response.
She gagged, and withdrew her mouth, streams of saliva trailing between her mouth and my dick.
I then rolled onto my side, reached out and felt her neck, then traced down to her breasts.
She let out a long hard moan as my fingers traced her left nipple, then I leaned in and took it in my mouth, swirling my tongue around it, tasting her sweat and feeling her chest rise and fall rapidly as she enjoyed my touch.
She pulled at my head, and I looked up, raised my head up, and our lips met, tonguing each other furiously, hands roaming all over each other’s body, exploring, touching, groping. There was no more slow, sensuous touching, it was not pure animal lust, a violent and desperate grinding and intertwining of my flesh with hers.
My right hand found its way down to her clit and I started to rub it from side to side, occasionally swirling my finger around. She was completely shaven and very, very wet. I inserted first one, then two fingers into her pussy. She opened her legs wider, lying on her back, knees bent. I finger fucked the shit out of her. She was thrusting her hips up to meet my fingers, crying out “more, more!” as I continued to finger fuck her. Soon I had three, then four fingers inside her. I felt her clamp over my fingers and she shook wildly, her orgasm so intense that she shook all over. The bed shook, and she yelled out, “fuck fuck fuck, shit, oh baby, fuck!”
I pulled my fingers out as she orgasmed, watching the outline of her body shaking, her back arched up and away from the mattress. Her hands roamed over her own body, massaging her breasts, and she rolled from side to side.
After a few minutes, the shaking subsided. She grabbed my dick, which was still hard and dripping precum. She took it in her mouth, tasting my precum, and laid down on her back, opened her legs, and simply said, “Fuck me. Fuck me now.” So I did.
I rose above her, directing the tip of my dick towards her pussy opening. Her hips came up to meet me. She was still very wet. I felt the tip slide inside her, and then quickly my full 8 inches entered her, enveloped in her pussy completely.
I paused for a second, listening to her sharp, shallow breathing. I was all the way inside my friend, unprotected. My dick had been in her mouth. I felt her hands grab my ass cheeks and she started to grind against me, so slowly I started to fuck her, in and out, a fairly slow but steady pace, until we found our rhythm. As I pushed in, she would grind her hips up against me, taking me deeper and deeper. Her legs wrapped around me, pulling me closer, and I could feel her naked flesh under mine as my hips thrust and my penis pushed deeper and deeper inside her.
She was moaning, “yes, yes, yes, yes, oh fuck yes”, and I felt my orgasm build. I continued to thrust deep inside her. I felt her get tighter around my dick and she let out a massive scream. Realising that she was cumming again, I started to feel my own orgasm building.
“I’m about to cum,” I said in between breaths. “I’ll pull out.”
“Don’t you fucking dare, I want all of you!” she said.
That was all it took. Another few thrusts, exhausted, I released spurt after spurt of cum inside her pussy. As I came, she started to cum again, and she said, “fuck, this is the best part,” referring to my hot cum deep inside her pussy.
My orgasm lingered, and I laid on top of her, still deep inside her, as she continued to grind against me, getting slower until she stopped. Still I laid there, enjoying her naked flesh beneath my own, and enjoying being inside her.
Eventually, I started to soften, and I pulled out. She immediately took me into her mouth, licking me clean. That was the first time my limp, cum-dripping dick had been inside someone’s mouth after an orgasm, and it felt oddly amazing.
Once I was clean, she sighed contentedly, laid back down, and said, “We are doing that again.”
Tommie Ann and I became fuck buddies for a long time after that. She says at one point she got pregnant to me, but I’m not sure about that. I got married again two years later, by which time Tommie Ann and I had lost touch and gone different ways. She never did have a kid, so I’m not sure what happened with the pregnancy.
Years later (2015) I was divorced again and had gone through multiple bad relationships, but had become somewhat of a sex champion (in my own eyes), having gone to bed with 29 different women in the space of 4 years. However, Tommie Ann and I reconnected, and started a weird “friends with benefits” type relationship again – our protocol was that I would sneak out after my girlfriend was asleep, Tommie Ann would give me a naked rub down/massage, then I’d finger fuck her before penetrating her. This went on for a while (I never told her I was seeing someone), and I even fucked her several times after getting married for the third time.
I enjoyed fucking her while it lasted. We live in different states now but have regular phone and video sex. I’ll maybe share some more stories of Tommie Ann, depending on how much people like this one.
