Normally I would be writing a story about my MILF FWB Erin, but this is not a story about her, although it indirectly involves her. Erin is a successful lawyer in my area. After our mall hook-up, she texted me a few days later and asked me out to dinner to talk to about something. I fully expected her to end our arrangement, but instead it was something totally different. Over dinner Erin explained to me that her secretary who had always been reserved and quiet about her personal life had started to open up to Erin. According to Erin, Abigail (the secretary) had revealed that she had been raised in a devoutly religious home and with incredibly strict parents who up until she moved out at 28, had been incredibly overbearing. Over the past few weeks Abigail(now 30) had revealed more and more about her life until she finally admitted to Erin to that she was a virgin and had considered hiring a male escort to take care of her “problem.” Basically, a long story short, Erin told her not to do that, and that she knew of someone (me) who could take care of her “problem” and who wouldn’t treat her just like a transaction.
Fast forward to this past weekend, Erin arranged for us to use her house because she was out of town, the only rule was using the guest bedroom. I got to Erin’s house first and let myself in using the door code. I poured two glasses of wine and waited for Abigail to arrive. Around 7:45, I heard a knock at the door and ran to answer it, when I opened the door, I was greeted by Abigail. I had seen a picture of Abigail, but it was from the shoulders up. Abigail was about 5’4 and incredibly thin, she probably only weighs 110-115lbs. She was wearing a pair of fitted but not tight jeans and a checkered blue sweater that fit her torso, but like her jeans wasn’t tight. I introduced myself and gave her a hug and a light kiss on the cheek. We walked into the living room and made small talk over the next half hour while drinking a couple glasses of wine. Abigail told me about herself, her upbringing, and how she felt like she was missing out and that guys she dated were put off that she was still a virgin. As we finished our wine, she looked at me, smiled and said, “Thank you for being willing to help me out with this, can we go upstairs?”
I smiled and lead Abigail up to the spare bedroom. As we reached the room, Abigail turned to me and said, “I’m going to let you take the lead. Erin told me your clean, and I started on birth control for period control after I escaped my parents, so we don’t need a condom.” I kissed her softly on the lips and pulled her close. We kissed passionately for a few moments before I allowed my hands to begin to wander to her ass, giving it a firm squeeze, causing her to pull away and take a deep breath. She looked at me and smiled and then leaned back in to kiss me more. As we continued to kiss, my hands left her ass and wandered up underneath her sweater, as my hand reached the back of her bra, she lifted her arms and allowed me to take her sweater off. I told her she could take my clothes off too, and she lifted my shirt off. As I leaned down and kissed her neck, Abigail gasped and let out a little moan and shiver. As I kissed down to her neck and collarbone, her moans began get more consistent. I reached down and unbuttoned her jeans and slid them down her body. I looked at her and smiled before saying, “I think I am over dressed, a little help?” She smiled and unbuttoned my pants and allowed them to fall to the floor.
As we both stood there in just our underwear, Abigail blushed and said, “I’m sorry but I don’t own any sexy underwear.” For the first time I realized that she was simply wearing a pair of very conservative white panties, and a plain, full coverage white bra. I just laughed, told her, “There’s nothing to apologize for, you look beautiful.” Abigail just smiled and said, “Thank you.” I pulled her back in to a kiss and we kissed for another minute or so before I unsnapped her bra and stepped back so it could fall away. As the bra hit the floor, I realized the Abigail had a very small bust (34A as I found out later.). Once again Abigail blushed and said, “You’re the first man to ever see me like this.” I told her, “Then I am honored, lets lay down.” As we moved towards the bed, Abigail said, “Before we do that, let’s get rid of the rest of these clothes.” We both took our underwear off and I noticed that Abigail had a full but trimmed bush.
As we laid down, we continued to kiss; as we kissed Erin’s hand began wander down before she asked, “Can I touch it?” I smiled and told her yes. She took my cock gently in her hand and gave it a slight squeeze. I told her, “Keep that grip and move you hand up and down.” She proceeded to give me what I would call a “teenager hand job.” It didn’t have much rhythm, but it did feel good. After a few minutes of this, I pushed her onto her back and climbed on top of her. I smiled at her and said, “Can I eat you out?” She blushed and said, “A man has never touched me down there, but if you want. I’m sorry it’s so hairy, I’ve been too nervous to shave, just trim.” I smiled and told her that it was fine, and I kissed my way down her body pausing to kiss her breasts and nipples before traveling the rest of the way to her bush.
As I moved between her legs, I could tell that she was wet. I lightly kissed her thighs causing her to jerk a bit before starting to moan. As I got closer to her pussy, her moans began to get heavier, I paused be starting and said, “I’m going to eat you out now, relax and enjoy it.” She mumbled some words that I couldn’t make out because I was starting to lick her pussy. I used just basic up and down strokes paying special attention to her clit. I kept this up for 2 or 3 minutes all the while her moans began to get more consistent and louder. I paused for a brief moment and slipped a finger into her causing her to go, “OH GOD!!” I stopped and looked up and asked if she was okay. She took a couple of deep breaths and said, “Wow, yes that feels amazing, I’ve only used my fingers and they are much smaller!” I smiled and lightly began to finger while licking her clit. This action caused her moans to begin louder and louder; I kept up my pace and within another minute or she let out a slight whimper/moan and I felt her pussy clamp down on my finger. I stopped with my finger but kept up licking her clit as she shook with orgasm.
As her orgasm subsided, I slid up till I was even with her, and she kissed me before remarking, “Is that all me on your face and beard?!” I smiled and told it was and when she started to apologize, I told her it was normal. We laid there with me softly cupping her breasts as she caught her breath until she said, “I’ve never given a blowjob and I think it might be too much, is that okay?” I told her it was and that we could stop now if she wanted. She smiled and said, “NO, I came here to lose my virginity, and that’s what I’m going to do.” I sat up and repositioned between her legs and lined my cock up at her entrance. Before I slid in, I said, “This may hurt for a moment, just tell me to stop, but I’ll go slow.” She just bit her lip and shook her head. I pushed into her with just the head, and she took a deep breath, so I stopped, after a moment I began to push more, I felt a tiny bit of resistance, but I was able to slide all the way in. As our pelvises met, she let out a loud moan that kind of shocked me. I asked her if she was okay and she said, “I’m great, I just feel so full!” I slowly began to pull out and thrust into her, each time causing her to moan louder and louder until she began to cum again. As she came down from her second orgasm of the evening, I began to pick up my pace, thrusting in and out of her with a little more force and making sure I pulled out almost all of the way before plunging back in. I would love to tell you I last for another 15 minutes, but due to her tightness and moans, that wasn’t in the cards tonight. I thrusted a few more times and right as she began to cum for a final time, I had enough sense to pull out and with two strokes of my hand, blew my load all over her stomach and a bit even reaching the bottom of her small tits.
Be both collapsed on the bed and began to catch our breath. After a few minutes of nothing but breathing, Abigail leaned over and kissed me and said, “Thank you for that! It was amazing and I’m glad my first time was withs someone so caring and experienced. Erin was right you do know what you’re doing!” I smiled as I told her thank you. I got up and got her a towel to clean up with. As I leaned against the headboard, Abigail got dressed and said, “Erin told me I could stay the night, but I need to get home to my cat.” I told her no problem and walked her to the door. After she had left, I texted Erin, “Abigail just left thanks for setting that up, hopefully she just doesn’t catch feelings lol!” Erin responded back a few minutes later, “Oh she won’t. Lol. I made it very clear that this was a one-time thing and that your cock was all mine.” I responded, “Well that is fine with me, I’ll get things cleaned up and locked up here.” Erin texted back, “Just stay the night, I get home early tomorrow, and you can use that hard cock on me. Thinking of you two tonight has gotten me pretty horny.”
Source: reddit.com/r/gonewildstories/comments/mzdtmp/took_a_secretarys_virginity_mf
Very erotic and well written.