Hello readers, this story is about my first anal sex. I hope you enjoy it half as much as I did.
So some years ago, I was added to a group on WhatsApp; it was a party group, trends and stories about the latest parties in town. I had already gained admission into the university, so I could party without massive scrutiny from my parents. My friend, who was one of the group admin adds me; being an introvert, I never texted as I knew no one on there. I would just check out the banters going on and have a good laugh but it all changed one night, when my friend decided to chat; I was glad. I finally had someone I knew, I texted and we were flowing really good till the bastard went off. It was like he took my confidence and I was silent for some time before a girl asked if I was there, her name: Sandra. I replied yes and we made small talk, then I asked if I could DM her which she acquiesced; I DM’ed her and we were flowing well till I had to sleep some minutes after 2am.
When I woke the next day, I texted her and never got a reply. I mean, she virtually read the message as it had the blue marker on, I texted her again and the same thing happened. I guessed she wasn’t into our conversation like I was, so I archived the chat. I was surprised when she texted me in the night, apologizing about her silence, I told her we were cool. Halfway through texting, we decided to trade pictures; she sent me some pictures and she appeared thick in those pictures. I quickly deduced she was a thick girl which was my favorite spec when it comes to the opposite sex. We graduated to calling and became quite attached, we sexted a few times after about 3 weeks; I asked her out via WhatsApp, she agreed and we became official. I wanted her to visit, and she said she would when she went for dance rehearsals; I didn’t know about that and she explained she loved dancing and took lessons too.
She decided to visit on a Thursday, she said she would ditch lessons so she could spend more time with me; I was pleased and gave her directions to my house. When she called to tell me she was in the area, my cock automatically started throbbing; I put on a shirt and went to get her. I got to where she supposedly said she was; I was on the lookout for a thick girl, and couldn’t find any; so I called her and this lithe, tiny and curvy lady picked up… In my head I was like “Oh wow, she isn’t thick”. I approached her and we hugged each other then I led her to my house. Once we were in, I led her to my room; which was sparkling clean and neat. She dropped her purse on the table and might I add; she wore a purple gown that accentuated her curves. Her ass was damn, she approached me and I grabbed her. She was so tiny and light, I kissed her and she kissed me back; I dug into her ass and she moaned into my mouth. I broke away from the kiss and nuzzled her neck, which had her moaning. I raised her gown up a bit and put my hands in her panties which felt like a “used towel”; she was damp. I cupped her cunt and inserted my middle finger into her, she was dripping wet; hot and tight. I thrusted my fingers in and out and she gripped my hair tightly and her vaginal walls clenched hard around my slender finger as she orgasmed.
I thought to myself, she must really be horny or I had gotten really good. After she rode the last waves of her orgasm, I pulled my hand out; my finger was really moist and I really wanted to taste her juices but I didn’t know what kind of scent or odor her cunt gave… so I pretended to nuzzle her neck, and quickly brought the naughty hand to my nose. There was no odor which turned on a lot of green lights in my head. I stopped nuzzling and put my middle finger in my mouth tasting what was left of her juices and she tasted really good, tangy is the word. She looked at me sucking on my finger and licked her lips, then she went on her knees, attacked my shorts and before I knew it, my cock was engulfed in her mouth; her mouth was as hot as her cunt, and I enjoyed the way she sucked my cock.
I put my hand behind her head and tried to fuck her mouth but her throat wouldn’t have it. I pulled out of her mouth and undressed her, while her ass was great, she had small tits. My palms cupped each one successfully but what she lacked in tits, her nipples made up for it; her nipples were not small as I would have imagined. I grabbed one and put my tongue to work, rolling my tongue around in circular motion; her nipples grew hard and I sucked hard on the one in my mouth before switching to the other.
My cock was throbbing and needed attention, I was still sucking when she pulled her nipple out of my mouth and told me she wanted me in her. I was thinking of where I dropped the condom I bought earlier and she produced one from her purse, I tore off the foil and donned on the condom. She had already laid down on the bed and I positioned myself between her legs and breached her cunt with the tip of my cock; she was really tight so I had to go in slowly. When my cock was halfway in, she moaned for me to stop that she couldn’t take anymore. I was wondering, I wasn’t even that big; I made do with the half and started thrusting into her slowly and she moaned with each thrust. Friction wasn’t a problem as her pussy was leaking her juices; her heat got me really good and I picked up pace, thrusting faster but still gently.
Some part of me was afraid if I went hard she would faint. She came three times around my cock before we changed positions and when I pulled out, I told her I wanted doggy. While she was getting into position, I noticed the way the sheets molded into the bed, when I slid into her again, I grabbed her ass at first and later held her shoulder while fucking her fast and I could hear my balls slapping against her. Each thrust seemed to make her cum and when I felt my balls tighten, I knew I just had to cum. I slammed in finally and I erupted into the condom and after spasming I pulled out of her and she literally collapsed on the bed; her hair matted with sweat and at that moment, I felt really proud of myself. I disposed of the condom and joined her on the bed, she was taking a brief nap. When she woke up, she showered and while she was cleaning off her body, I admired her ass and wanted anal right that moment. I said nothing, I helped her dress up and saw her off. We fucked at least two times weekly and she was already adjusting to my size and taking more of me in.
Three weeks after our first encounter, we were playing Truth or Dare in the night and I asked her if she would like to have anal sex to which she replied no. I told her I wouldn’t hurt her and that I had read all about it, then she asked about the mess and I explained how we would deal with it and she said she would think about it. She was supposed to visit that week but she never showed up; she made up one excuse after the other. I had already forgot about the anal sex thing till she mentioned it on Wednesday night and told me she wanted it and asked if I was sure I knew what I was going to do and I told her yes. While I was supposed to be asleep, I researched about Home given enemas, I didn’t have money to purchase any of the items, so I decided to make a makeshift enema kit. The next day, I literally broke into my mom’s room; she’s a nurse and I was guessing I could find some tools. It was my lucky day, I found a catheter and a drip bag. I fixed one end of the catheter into the drip bag after filling it with water and tried to see things, I turned the bag upside down and water flowed out of the other side of the catheter; at that moment, I felt I had achieved something in life. After searching online and discovering I had none of the other ingredients; I settled for lemon juice and olive oil.
On Friday, I halved about 5 lemons and squeezed em into a bowl, then I put them in hot water to be able to squeeze out nor juices, I was home alone and my girlfriend arrived early about 11 am, after letting her in, I kissed her and told her I’d be with her shortly. I heated some water and I poured it out into a bowl to allow it cool; I brought out the tools and my girlfriend got scared and I had to make sure she wanted to go along with it. After testing that the water was warm and wouldn’t hurt, I added the lemon juice and stirred it with a spoon, then I poured it into the bag and tightened the lid. I asked her if she was ready and she said yes; we headed to my room where she undressed and I grabbed the bottle of olive oil I had taken from my mom’s room. We entered the bathroom and I asked her to bend at the waist, like a standing doggy style; then I greased her ass hole with some olive oil and she moaned, I greased the other end of the catheter and I slowly eased it into her, as the catheter was gentle on the skin, it actually eased into her without problem. Then I raised the bag up to allow water flow into her colon, at this point she held out her hands to the walls and then said to stop, I pulled out the catheter and helped her massage her abdomen, she held the water for a minute I think, then she let it out. We repeated it two more times and I asked her to wash up which she did, I was already naked when she headed back into my room. Her perky tits got my cock harder than my thoughts already did and I helped her dry her body, then she took my cock in her hands and stroked ever so gently. She went on her knees and sucked my cock, I wanted to do anal so bad. I told her to stand and wore a condom which I lubed up with the olive oil and she bent over my bed as I lubed up her asshole.
I put my cock to her entrance and pressed it in, her hole wouldn’t open up so I applied some pressure and when my tip was in, she moaned really loudly. I put some more in and she shouted enough, so I had to fuck her with about a quarter of my cock. She was so tight and hot and the oil aided friction, I thrusted ever so slowly and she moaned really loud, her hole was opening up to the intruder and taking more of my cock in. When I was halfway in, I increased pace and she gripped the headboard of the bed, I had my hands on her phat ass as I took her virgin asshole; At some point, I slid my finger into her cunt and she was dripping wet. I tried to simultaneously fuck both holes with my cock and finger but I couldn’t do it for long, I pulled out of her asshole and grabbed a chair. I motioned for her to stand up but she wouldn’t. I had to help her up, and position her over my cock, it was the reverse cowgirl position and she sat down gingerly on my cock, dictating the amount she took in and the pace; she rode my cock slowly and I cupped her breasts.
I knew I couldn’t take much more, she changed positions and straddled me; putting her breasts right in front of me and I sucked on them. She only sat on my cock in this position and she was heaving and breathing fast. I knew she was exhausted so I grabbed her ass with my hands and helped her ride my cock and on the 4th thrust, my cock slipped out of her asshole and I told her I was going to cum. She knelt down and immediately I took of the condom, I painted her white; coating her tits with my thick, pearly white cum. We cleaned up after and made small talk before I claimed her pussy again. Her legs were all wobbly when she was about to leave and I had to guide her to the junction where I got her a bike and kissed her goodbye.
It continued this way till I resumed school before we eventually parted ways.