My First Blowjob, a Late Bloom

tagFirst TimeMy First Blowjob, a Late Bloom

I am reflecting on the months that led up to my thirtieth birthday. That was the year I was widowed after a ten year marriage. Needless to say I started some serious self exploration. It was a fine marriage, although his death didn't induce the deep grieving people describe. I spent most of my grieving weeks rethinking the decade of memories.
We started dating in high school and married young. At the time of his death I still barely understood love. We definitely loved each other at some level. Yet the reason for getting married wasn't love. Maybe convenience? More likely part guilt. We started having sex as teens which we both understood was wrong. Instead of admitting what we were doing we resolved our guilt through marriage. Once married the teen age sex no longer mattered.
The decade flew by having two kids and trying to present publicly as a good family. I had three consistent friends since high school that also didn't know my true self. How could they when I didn't know myself. Immediately after his death I started being unusually honest with my friends. They were totally surprised when I I admitted to them how my marriage was lacking.
For example, these three women were always sharing serious sex stories about their husbands. Initially I couldn't believe these stories were true as their lives seemed so different than mine. Amy and Lisa, and their husbands, would travel together as couples. Their best stories came from cruises. Together they would spend time on the topless deck. I hid my shock. The idea of their husbands seeing me naked was mortifying. In actuality, my own husband never saw me naked in the light. Kim, the third friend, shared some of her most intimate acts with her husband, most of which I couldn't even contemplate until porn finally arrived on our internet.
And the oral sex; all of them gave blow jobs constantly. I was told as a girl that oral sex was bad, always in the form of a blowjob, and unenjoyable. But all three of my friends seemed to relish giving head. And then there was the stories of their husbands licking their pussies. Amy and Lisa's husbands seemed to be eating them out on every trip away from home. How could they enjoy that? I couldn't imagine anyone even looking at my pussy let alone getting their mouth close to it.
Over one dinner with the four of us I admitted how bad my sex life was. Yes we had sex early, but it was anything but fun. From the very beginning he nearly refused to even touch me with his hands. Once he was hard he just wanted to fuck. The sex wasn't even that good, maybe 5 minutes, and when he was done it was over. Once married the frequency was almost comical. He seemed to need it about once a month, which was always the same five minute release. I was never comfortable making suggestions, not that I had any desires to make.
My husband and I were friends, and he was never abusive. My marriage just seemed like two high school friends raising kids. My friends were astonished. Kim politely accused me having lied all these years. She sincerely wished she could have helped but wasn't sure why I had deceived them. How could I not? Their marriages seemed so fantastical and mine was the odd one out.
I had lied. Mostly by omission. When they told me exciting sex stories I didn't know how to respond. At first I didn't believe them. Then when it was obvious that their relationships were normal and mine was abnormal, I couldn't admit how different I was. Mostly I just responded with "yup, I know what you mean." The worst lies were when I repeated back their stories as my own with small variations. Always just enough to redirect the conversation away from me. I gave limited details so that it wasn't obviously false. Ignorance was hard to hide but they didn't seem to dig deep enough to catch me.
Mostly these three were apologetic for not knowing my truth. They wished they had helped but mostly I felt their sympathy. They made it clear that they were very glad for the sex they are still having all of these years.
Still, our friendships were close enough for them to finally stop talking and to listen. They were glad I found porn, and there was no shame since they all also watches porn. I learned they watched alone for themselves, as do I, but also with their husbands for more sex fun. They heard me explain how the only fingers that have ever been in my pussy were my own. My only orgasms were my own and that only started two years before my husband's death. My husband never saw me naked as we only had sex in the dark and in bed, except for the few times in a car before we were married. I never even gave him a blowjob as he thought that was weird. So we shared five minute missionary sex once a month for a decade. The rest of my sex life was listening to their storie and dreaming while watching porn.
We kept getting together to talk twice a week. Everyone supported my reprogramming of sex and marriage. Their husbands would watch my kids in solidarity of our now new level of honest friendship. To expand our talks beyond my shocking marriage stories, I asked them to share more of their sex stories. And boy did they ever. I didn't think their stories could get any wilder but until I asked for everything they had, they must have been holding back.
Amy and Lisa, during their many travels together, said they let loose whenever they leave town. They each admitted to drunk naked dancing in bars in Las Vegas. One got up on the stage as an impromptu stripper show. One trip to Rome they admitted to having sex in the same room with each other. There was no swapping or anything like that, just each couple having sex in the same room at same time as the other couple. Wow, seeing your friend's husband naked seemed phenomenal when I never even showered with my husband.
Kim admitted to making out with a woman while her husband was sitting next to her. And then she described the wild sex that followed that night. She claims some of their sex lasted more than two hours. I can't even imagine what two people would do for two hours. Even after watching porn I didn't have that many ideas. I usually only had a few minutes to watch porn and touch myself for a while before going to bed.
I wanted to feel some of what they were sharing. But it seemed like it would take forever to get that comfortable. We four started talking about possibilities for me. It was fun and exciting to describe stories; none of which seemed likely. Kim wanted me to get eaten out. She loves being licked until she comes and was sure that was what I needed; unabashedly selfish sex. Amy and Lisa thought I should start tamer with a good finger bang. They admitted further that after that same room sex story their husbands kept finding places to finger fuck them in front of each other. My head was spinning. What would be going through your mind to have someone watching while I was being touched. Even with clothes on, those stories were unthinkable.
Ultimately I told them that I wasn't ready to be that exposed. Although having someone reach down my pants and finger me was the most appealing. When pressed for my wish for a future sex act I admitted to wanting to give my first blow job. Kim still couldn't believe I never had a dick in my mouth after having so many years of implying that I did give head. This was all a few weeks before I turned 30 years old. They finally understood why I would choose to give head before I'd feel good enough to accept anything myself.
The three focused their advice on my first blow job. Who could it be? Must be someone they trusted. Someone that would understand my situation and be sensitive and safe. Then there were the details. How to give head. Lisa asked if I wanted to watch her give head to her husband. "No!" good grief, I know these guys. That would be too weird. And what to do with the cum. The only cum I've experienced is what dripped out of me. I hadn't even given a hand job to completion so even cum handling would be new for me. They all agreed I shouldn't swallow but just blow a guy until I could watch him cum with my hands. When I got home I searched for similar porn, which there were many.
Upon reflection It came out that I actually had a prospective friend. Jeff worked in the same accounting firm as me but in an office across town. He was covering for someone in my office a couple of years ago during the time he lost his wife. We had lunch a few times and became acquainted. He contacted me when he heard I was also widowed. I felt safe with Jeff. He shared some post widow dating stories but wasn't pushy. It was clear we wouldn't be a future dating potential as we had some age differences and he didn't date women with kids, but with our shared experience we could call each other whenever needing to talk. Jeff was the only single male friend I knew at the time.
Kim jumped on Jeff as the prospect. She met him at a few work events and agreed I should pursue him. She even volunteered to talk to him and explain the situation. I was hesitant about their wanting to help but knew I had no experience in making this happen organically. I also wanted to do this before I started dating again. My lack of confidence and experience could sabotage the simplest of dating. All three agreed with my giving Jeff my first blow job, maybe a bit too eager.
It wasn't even a week after I agreed Kim could call Jeff that she had it arranged. Jeff, being the nice guy that he was, took some convincing. He was sure I needed to be pleased first, and he was totally interested in giving me a good sexual experience. Kim got Amy involved and she better explained why that wasn't my preference. Jeff agreed as long as I told him directly of my wish. I wanted to simply go to his house and give him head with little interaction. I dreaded a conversation. Jeff understood from his dating experiences after a fifteen marriage and would make it easy on me.
Jeff and I texted and agreed on a date. My friends eagerly created plans. Kim took my kids overnight and Amy would stay with me after the deed was done so I had someone to share my experience. Jeff assured me I was in total control but he would guide some details to keep me relaxed.
On the planned night I went to Jeff's house. It was 10:00, early enough to be awake but late enough not to linger after. Jeff met me at the door and brought me to his kitchen. He held my hand in the nicest way while asking me for confirmation of my desire. He made me a drink then suggested he script some of the next hour. I downed one drink from nerves and appreciated his attentiveness.
We went to his back patio room where he already had some music playing. The room was dimly lit with two candles on a mantle. We faced each other holding hands. He asked again if he could touch me or undress me and I confirmed that I wanted to stay dressed. I did give him permission to touch me anywhere he wanted on top of my clothes. He suggested being comfortable with a naked man's body was important for future dating. I took his advice and decided I should undress him. I asked him to close his eyes which he did respectfully.
I then pulled his shirt up over his head. Jeff was older than my husband but still very fit. My husband would be shirtless when we went to the beach but that was the most of his body I ever explored visually. The rest of this would be new territory. I ran my hands through his hair touching his face. Jeff kept his eyes shut but smiled from his own nerves. I ran my hands down his chest feeling his strong pecks. Even when my husband was shirtless I never explored his body this way. My hands slid down his stomach and around his back. Knowing Jeff wasn't watching me I felt free to explore and reached around touching his back and shoulder blades. The only skin I touched over the past decade with this intensity was my own. His skin was warm yet cool. I knew men liked younger women but Jeff's age wasn't a problem for me. Here was a strong man's body fully accessible to me.
Jeff sensed I was pausing and asked me to confirm I wanted to continue; which I did. He assured me he would keep his eyes closed which was definitely needed to calm my nerves. He grabbed my hands and placed them on his jean front. It was now up to me to unbutton his pants. I took a breath and opened the tops. I lowered the zipper and pulled his pants down as he lifted his legs to pull them off. Jeff was wearing the cutest briefs with birds on them. This man was fun and playful. He was now standing in front of me naked except for these printed briefs. Jeff stayed quiet as it was clear I knew what to do next.
I grabbed his waist band and pulled his briefs down to his feet, in doing so my face came very close to his penis. I stood back up, stood back slightly holding his hands for stabilization, and just looked at his body. For the first time this evening my body twitched sexually. Since my marriage, this was the most sexually aroused I got except for watching porn alone. Jeff wasn't even erect which surprised me. My husband had always been stiff before he would ask me to touch him. I let go of Jeff's hands, ensuring his eyes were still closed, and reached forward to touch his penis. My fingers slid up and around it. The air was cool and his scrotum was quite tight. I hadn't really looked at a scrotum before. Yes it was strange looking, just as my friends made fun of scrotums, but it was soft to the touch. I held the entire thing in my palm as his penis began to fill and rise. I grabbed the swelling penis with my other hand as it got more and more hard. At this point I can see why it is called a cock. Still strange looking, the way it felt made me feel arousingly beautiful. I stood there lightly stroking it. Jeff remained quiet.
My hands kept moving but overall I was frozen. I finally spoke and asked Jeff what I should do next. He didn't say anything with words but fell back on the couch pulling me to the floor in front of him. Jeff leaned his head back still with closed eyes. I was kneeling in front of him with both of my hands now stroking a fairly long erection. Jeff's hands were resting on my forearms as I stroked him. With one hand I reached over for my second glass and finished the contents. As I returned I leaned in and lowered my mouth over the tip of Jeff's cock.
It seemed to fill even fuller, getting stiffer and thicker. I was amazed at how it's shape kept evolving. My only experiences with erections were five minutes pumping inside of my pussy. Here I was exploring an erect cock using several senses. I knew what to do next from listening to my friends stories and from watching porn. I slowly slid my mouth down his shaft, farther and farther. It seemed to take forever to reach my limit. I pulled it out and started to lick up and down the shaft. It tasted like any skin that was recently washed. It would jump every now and then depending where my tongue touched. I pushed it back down in my mouth. I wasn't sure how to keep this exciting for him but I liked being in control of the pace and exploration.
I pumped my head up and down several times before stopping to ask questions. Did this feel good? Should I be doing something else? How long would this take?
Jeff was the perfect partner. Yes it felt great. I should vary my actions however I wanted to explore and respond to his reaction. He said he could last for as long as I wanted and could finish whenever I got tired. He told me my jaw could get tired which is something no one told me before. I was surprised he could stay this way as my husband never lasted very long.
His hands ran though my hair which was tantalizing. They would roam down my back, and he even fondled my breasts over my shirt. I was aroused and could finally see the fun in this. Everytime I made him squirm, or get his cock to jump, it made me that much more aroused. The more aroused I got the more I wanted to blow him. It was a very positive feedback loop.
I increased my pace and was really pumping my mouth. I used my tongue to add pressure which he seemed to like. Several times when my jaw would get tense I relaxed and pressed his cock way back into my throat until I nearly gagged. I found it very arousing to get right to a gag. I was in total control of Jeff's completely naked body. My hands kept exploring his chest when I pushed him the furthest down my throat.
Jeff reminded me that I didn't owe him a finish and could end any time. I looked and it had been nearly 30 minutes. I couldn't believe he was lasting. I gave him a solid handjob for a while to rest my jaw more. I decided I wanted to see a man cum and ask him if he would make that happen.
Jeff was still sitting and moved horizontal on the couch. I was still kneeling and enjoyed seeing his body in this position. He said if I blew him for a few more minutes he would tell me when I was going to cum and I could give him a hand job to the end. Just hearing him explain this in his words was sensual. I was totally turned on and couldn't wait to finger myself later for my own orgasm.
I grabbed his cock and balls with one hand and really started giving him head. His breathing got faster and deeper as his cock started getting fuller again. I placed his hand on the back of my head to give me some feedback. Jeff ever so lightly thrust his hips pushing his cock faster in my mouth. Just as his breathing got intense he pulled my head back and I grabbed his cock with both hands. He started cumming hard, arching his back. His cum was squirting on his stomach and all over my hands. My hands felt the pulsation through his cock which was now relaxing and thinning. I asked what to do next and Jeff said I could stroke him more for a while or stop whenever I wanted. His cum was messy but gave my hands a lot of lubrication. I enjoyed making his body continue to squirm as he was clearly still sensitive. Soon his cock started reducing in size and I knew it was time to stop.
Jeff opened his eyes for the first time to reach over for the box of tissue. It was thrilling when he looked down and saw my hands still wrapped his thinning erection. We both wiped up the cum and I wiped off my hands. Jeff knelt next to me, looked me right in the eyes, and gave me a welcomed kiss. He was so gentle and appreciative. I had chosen the right person to guide me through my first blow job a few days before my thirtieth birthday.
Jeff led me to the bathroom to clean up more while he got dressed. We hugged but I told him I wanted to go home. Amy would be there to recap my evening although I was still looking forward to fingering myself. I just played with a man's body for almost 40 minutes until he came and it was completely exciting. I said goodbye and drove home.
Amy was great. She listened to my story completely. And affirmed my different experiences at just the right times. After I assured her I would rather be home alone than have her stay, she gave me a present from all of them and left. I opened the box after she left to find my first vibrator; a well chosen gift.
By morning, fully satisfied and pleased with my previous evening, I started contemplating what would come next. I have the best friends. And expect the next decade to be completely better.

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